Q & Answer: How Do You Pick the Right Shoe Size Online?

Zack writes to us to ask: I’m interested in buying a pair of shoes online, but am having trouble figuring out if they’d fit. I emailed the manufacturer and they gave me the length and width measurements in millimeters. The problem is, I don’t know whether the longest part of my foot aligns with the longest part of the shoe. Do you have any suggestions for what measurements I should ask for, so I can make an educated guess?

I’m not a big fan of measurements for shoes. Like you, I never know what I’m supposed to do with them. 

The length of a shoe can vary depending on a few factors.

  • Size, most obviously. But you’d be surprised how little changes from size to size. The difference can be as small as an eighth of an inch.
  • Welting technique. By welting technique, I mean how the sole was attached to the uppers. The length of your shoes — as measured from the bottom of your soles — can vary depending on the welting technique, as well as within the same kind of construction. Check out the two shoes above, for example. One is from Allen Edmonds, the other from Edward Green. Both are made with Goodyear welts, but the heel on the Allen Edmonds sticks out a bit more from the heel cup, while the heel of the Edward Greens hugs the shoe. 
  • Heel design. Although not as common, some shoes will have what’s known as a canted or Cuban heel, such as these from Saint Crispin’s. Again, compare them to the straight-down heel of the Allen Edmonds shoe above, and you can see how this would affect the measurement of the shoes at the bottom of the sole. 
  • Most importantly, the last. The last is the wooden form on which the leather is pulled over so that it can take a certain shape. You can have lasts in all sorts of shapes. Some shoes can be round and stubby (like Alden); some can be very long and pointy (like Gaziano & Girling). This will affect the length of a shoe more than anything else. You can have two perfectly fitting shoes, but one might be slightly longer simply because the toes were designed to look sleeker. 

In the end, it’s not even the length of your shoes that matter, but rather the heel-to-ball measurement. Critical to your fit is where the heel and ball of your feet sit in your shoes, not whether the ends of your shoe come within a certain distance to your toes.

There’s really only one way to figure out your size online, assuming you can’t try stuff on first.

  • Figure out your Brannock size. Go to a place like Nordstrom and ask someone to measure you. It’s sometimes good to get both feet measured, as few people have the same sized feet. 
  • Ask the store or manufacturer for advice. Not all salespeople will know what they’re talking about, so take their advice with a grain of salt. That said, there are few better places to get sizing advice than from the store or manufacturer you’re buying from. They’re the ones who are likely to be most knowledgeable. Tell them your Brannock size, and if you have other high-end shoes, your size in other brands and models. I don’t mean sneakers like Nike, but rather dress shoes from companies such as Allen Edmonds, Alden, Crockett & Jones, etc. 
  • Check this advice against the forum threads. Styleforum has the biggest archive of all clothing forums, but depending on what kind of shoes you’re buying, Superfuture and Ask Andy About Clothes can be useful as well. Iron Heart and Denimbro are also good for workwear type stuff. The key here is to search the archives before posting anything, as there’s usually a wealth of information you can mine. 

Finally, once you get your shoes, you can check to see if they fit according to this post.

Long story short: measurements are good for clothes, but bad for shoes. To find your size, you have to do some other stuff.

(Photos via Leffot, The Shoe Buff, and Bengal Stripe)

A Summertime Favorite: Penny Loafers
Once the weather warms up and the days get long, I often find that the best shoes are either sneakers or slip-ons. I typically wear sneakers with jeans and casual outerwear, and slip-ons with dressier trousers and sport coats. Styles can really range, but most of the time, sneakers tend to be white and minimalistic, and the slip-ons tend to be penny loafers.
The penny loafer is often thought of as a quintessentially American shoe — a style that’s most at home with tweed jackets and Shetland sweaters, as they were originally worn on Ivy League campuses in the mid-20th century. Today, however, you can safely wear them without any preppy connotations (although, you can also wear them as such, if you wish). With a sleeker pair of European pennies, for example, you can combine them with a soft-shouldered sport coat, wool trousers, and an open collared shirt for a very dégagé Continental look. With some beefroll loafers, jeans, and a light jacket, you can go back to looking like an American, but in a way that doesn’t feel too preppy. 
If you haven’t yet got yourself a pair, consider some of these:
Highly expensive at $750+: JM Weston’s 180 moccasin and John Lobb’s Lopez are pretty iconic, with the first having uniquely high walls around the toe that help distinguish it from the pack. My favorite loafers in this price tier, however, are all from Edward Green – an English firm known for its tasteful designs, quality construction, and beautiful finishing. Check out the Piccadilly, Montpellier, Sandown, and Harrow to start.
Pricey options between $350 and $500: Less expensive, but no less well-made, are loafers from all of your usual suspects. Carmina, for example, has something that looks very much like Edward Green’s Montpellier, while Alden has a wide range of handsome American designs. More recently, Wildsmith (a bespoke shoemaker once famous for their unlined loafers) relaunched as a ready-to-wear brand, and although their loafers aren’t as close to their originals as Edward Green’s Harrow, they’re priced competitively. Shipton & Heneage will also have a nice range of options, and they’re made a bit more affordable through the company’s Discount Club. Additionally, Crockett & Jones is very much worth a look, as are Alfred Sargent, Sid Mashburn’s house line, Kent Wang’s antique calf loafers, and the newly launched Paul Evans.
A bit more affordable at $350 and below: Of course, for more affordable shoes, there’s always Allen Edmonds’ factory second store, where the company heavily discounts shoes that didn’t pass quality control. Flaws are often very, very minor, if even visible at all. Loake’s 1880 line is also worth a look, and they sometimes produce for Charles Tyrwhitt and Herring (just note that some Loake-made shoes aren’t of terribly good quality, so use good judgment). Similarly, Ralph Lauren and Brooks Brothers will have some nice models, even though their quality can really range. Stick to the stuff that retails for $350 and above, and wait for end-of-season sales. In addition, Meermin offers some of the best price-to-value ratio right now in footwear, especially once you take into consideration their made-to-order program, and Jack Erwin is the best I’ve seen in the sub-$200 price range. For more American styled loafers, check out Rancourt and Bass’ Made in Maine collection.
Shell cordovan: Lastly, shell cordovan loafers are worth highlighting. Although shell cordovan is traditionally a workboot material, it works wonderfully today for slightly dressier styles (think wingtips, tassel loafers, and penny loafers). Alden’s Leisure Handsewn is a really beautiful American model, while Carmina will be more European. Meermin may also be able to make you something through their made-to-order program.
(Pictured above: Hooman Majd in his fifteen year old Edward Greens)

A Summertime Favorite: Penny Loafers

Once the weather warms up and the days get long, I often find that the best shoes are either sneakers or slip-ons. I typically wear sneakers with jeans and casual outerwear, and slip-ons with dressier trousers and sport coats. Styles can really range, but most of the time, sneakers tend to be white and minimalistic, and the slip-ons tend to be penny loafers.

The penny loafer is often thought of as a quintessentially American shoe — a style that’s most at home with tweed jackets and Shetland sweaters, as they were originally worn on Ivy League campuses in the mid-20th century. Today, however, you can safely wear them without any preppy connotations (although, you can also wear them as such, if you wish). With a sleeker pair of European pennies, for example, you can combine them with a soft-shouldered sport coat, wool trousers, and an open collared shirt for a very dégagé Continental look. With some beefroll loafers, jeans, and a light jacket, you can go back to looking like an American, but in a way that doesn’t feel too preppy. 

If you haven’t yet got yourself a pair, consider some of these:

  • Highly expensive at $750+: JM Weston’s 180 moccasin and John Lobb’s Lopez are pretty iconic, with the first having uniquely high walls around the toe that help distinguish it from the pack. My favorite loafers in this price tier, however, are all from Edward Green – an English firm known for its tasteful designs, quality construction, and beautiful finishing. Check out the Piccadilly, Montpellier, Sandown, and Harrow to start.
  • Pricey options between $350 and $500: Less expensive, but no less well-made, are loafers from all of your usual suspects. Carmina, for example, has something that looks very much like Edward Green’s Montpellier, while Alden has a wide range of handsome American designs. More recently, Wildsmith (a bespoke shoemaker once famous for their unlined loafers) relaunched as a ready-to-wear brand, and although their loafers aren’t as close to their originals as Edward Green’s Harrow, they’re priced competitively. Shipton & Heneage will also have a nice range of options, and they’re made a bit more affordable through the company’s Discount Club. Additionally, Crockett & Jones is very much worth a look, as are Alfred Sargent, Sid Mashburn’s house line, Kent Wang’s antique calf loafers, and the newly launched Paul Evans.
  • A bit more affordable at $350 and below: Of course, for more affordable shoes, there’s always Allen Edmonds’ factory second store, where the company heavily discounts shoes that didn’t pass quality control. Flaws are often very, very minor, if even visible at all. Loake’s 1880 line is also worth a look, and they sometimes produce for Charles Tyrwhitt and Herring (just note that some Loake-made shoes aren’t of terribly good quality, so use good judgment). Similarly, Ralph Lauren and Brooks Brothers will have some nice models, even though their quality can really range. Stick to the stuff that retails for $350 and above, and wait for end-of-season sales. In addition, Meermin offers some of the best price-to-value ratio right now in footwear, especially once you take into consideration their made-to-order program, and Jack Erwin is the best I’ve seen in the sub-$200 price range. For more American styled loafers, check out Rancourt and Bass’ Made in Maine collection.
  • Shell cordovan: Lastly, shell cordovan loafers are worth highlighting. Although shell cordovan is traditionally a workboot material, it works wonderfully today for slightly dressier styles (think wingtips, tassel loafers, and penny loafers). Alden’s Leisure Handsewn is a really beautiful American model, while Carmina will be more European. Meermin may also be able to make you something through their made-to-order program.

(Pictured above: Hooman Majd in his fifteen year old Edward Greens)

The Language of Penny Loafers

As the weather gets warmer and we inch closer to summer, I most look forward to when I can wear my penny loafers again. I pair them with everything – linen suits, wool trousers and sport coats, chinos and madras shirts, and even the occasional pair of jeans and a button-up. While the style is versatile, however, every pair of pennies may not be. I find that the ones that look best with tailored clothes, for example, don’t go that well with jeans. The difference is all in the detailing.

Toe Construction

Every pair of penny loafers has a U-shaped ridge that bounds the top of the toe. On my dark brown calf Edward Greens, this ridge is made with a decorative top stitch that results in a very clean line. On my dark brown suede Rancourts, the uppers and sides are handsewn together to form what’s known as a “moc toe” (moc being short for moccasin). It’s a slightly rougher looking line, and this roughness only becomes more so with time, as moc toes tend to loosen with wear. Finally, my tan-suede Ralph Laurens have the most prominent ridge of all, with the top piece of the leather folded down and stitched to the sides.

Generally speaking, the last two styles are a bit more casual than the first, if only because they’re rougher and more prominent looking. I find that they go better with slim chinos or jeans, but if you have a more casual sensibility with tailored clothing, they could work with those styles as well. Conversely, the decorative skin stitch technique tends to be the dressiest. You can see this a bit more easily when you compare those Rancourts above to these Aldens. Both are very American in style, but the Aldens are just a tad dressier.

Toe Box Shape

All things being equal, the sleeker the toe box, the dressier the shoe. In this regard, my dark brown calf Edward Greens are the dressiest, while the dark brown suede Rancourts are the most casual.

Color and Material

Like with all shoes, black and dark browns tend to look dressier, while lighter colors (and non-traditional colors) will look more casual. Calf also tends to be dressier than shell cordovan or suede. This is especially true over time, as suede “balds” with wear. This is because, while you can hide scuffs on calf with shoe polish, there’s little you can do about scuffs on suede. This isn’t a bad thing, as quality shoes look better well-worn, but it does mean that wear tends to show up more on suede than anything else.

It’s easy, when choosing a penny loafer, to find yourself drawn to whatever looks dressiest and sleekest, but beware. While those styles may suit you, it’s useful to think hard about what you might wear your loafers with. If it’s something like chinos or jeans, you might do better with something made with a moc toe or beefroll (beefrolls refer to the visible stitching on the sides of the penny strap, which resemble a cut of beef tied with cooking string). There’s language in penny loafers that will dictate how you can best wear your shoes. As Charles Eames once said, “The details are not the details. They make the design.”

The Very Versatile Casual Suit
I love suits, but being that I don’t work in law or finance, don’t live on the East Coast, and am (what I’d like to think) a relatively young guy in his mid-30s, I don’t get to wear them very often. So, I buy most of mine these days in causal materials, such as cotton, linen, and corduroy. That way, I can have a casual suit for social occasions, or break the pieces up and wear them separately. In the above, for example, the brown sport coat is actually a suit jacket that’s part of a cigar linen suit I bought last year.
With a casual suit, even the trousers can be worn separately. Corduroy, linen, and cotton suit trousers just become … well, corduroy pants, linen pants, and chinos. And since these pieces came as part of a suit, the jacket’s length will be a bit longer than most sport coats these days (which often look too short anyway) and the pants will have a slightly higher rise (which I think looks more flattering anyhow).
The only downside, of course, is the cost. A good suit – whether made from a fine worsted wool or a more casual material – can run you $1,000 or more at the retail level. Depending on how you break up that price, that’s a lot more than what you’d typically pay for a casual pair of pants and a sport coat. Those won’t match up to form a suit when you need them to, but they will be less expensive.
If you can afford them, however, casual suits can be great, and they’ll give you a lot of versatility in your wardrobe. You can find them at most places that sell tailored clothing (try our suit buying guides here and here). No Man Walks Alone also has a rare Minnis Fresco option this summer. Fresco is an open-weave, worsted wool (which makes it breathable on hot days) and it has a bit of a texture (which means you can wear the jacket as a sport coat). Remember: the rule of thumb for wearing suit jackets as sport coats is to avoid anything that’s made from a very silky or finely woven wool. It should never look like you’re wearing a suit jacket by itself, even if you are.
Pictured above: tan linen pants from Hickey Freeman; cigar linen suit jacket by Napolisumisura (made from W. Bill linen); light blue shirt by Ascot Chang (made from Simonnot Godard chambray); dark brown loafers from Edward Green; dark brown belt from Brooks Brothers; and white cotton pocket square from Simonnot Godard

The Very Versatile Casual Suit

I love suits, but being that I don’t work in law or finance, don’t live on the East Coast, and am (what I’d like to think) a relatively young guy in his mid-30s, I don’t get to wear them very often. So, I buy most of mine these days in causal materials, such as cotton, linen, and corduroy. That way, I can have a casual suit for social occasions, or break the pieces up and wear them separately. In the above, for example, the brown sport coat is actually a suit jacket that’s part of a cigar linen suit I bought last year.

With a casual suit, even the trousers can be worn separately. Corduroy, linen, and cotton suit trousers just become … well, corduroy pants, linen pants, and chinos. And since these pieces came as part of a suit, the jacket’s length will be a bit longer than most sport coats these days (which often look too short anyway) and the pants will have a slightly higher rise (which I think looks more flattering anyhow).

The only downside, of course, is the cost. A good suit – whether made from a fine worsted wool or a more casual material – can run you $1,000 or more at the retail level. Depending on how you break up that price, that’s a lot more than what you’d typically pay for a casual pair of pants and a sport coat. Those won’t match up to form a suit when you need them to, but they will be less expensive.

If you can afford them, however, casual suits can be great, and they’ll give you a lot of versatility in your wardrobe. You can find them at most places that sell tailored clothing (try our suit buying guides here and here). No Man Walks Alone also has a rare Minnis Fresco option this summer. Fresco is an open-weave, worsted wool (which makes it breathable on hot days) and it has a bit of a texture (which means you can wear the jacket as a sport coat). Remember: the rule of thumb for wearing suit jackets as sport coats is to avoid anything that’s made from a very silky or finely woven wool. It should never look like you’re wearing a suit jacket by itself, even if you are.

Pictured above: tan linen pants from Hickey Freeman; cigar linen suit jacket by Napolisumisura (made from W. Bill linen); light blue shirt by Ascot Chang (made from Simonnot Godard chambray); dark brown loafers from Edward Green; dark brown belt from Brooks Brothers; and white cotton pocket square from Simonnot Godard

It’s On Sale: Edward Green Shoes

Edward Green is my favorite shoe brand, but they are very expensive. At Brooks Brothers, for example, they go for about $1,300-1,500 a pair. Are they worth it? Well, they won’t last you any longer than the ~$250-350 shoes you might buy from Allen Edmonds, Paul Evans, or Meermin, but they do look very, very beautiful. They use great materials and have exceptionally nice finishing techniques. What that effectively means is: the interior will feel slightly nicer, and the uppers will be colored in a way that gives them some visual depth. 

Unfortunately, they’re rarely discounted, which makes Ashton Marks’ sale on them notable. Included is a very useful black cap toe (in two widths), some brown wingtips, and a couple of loafers. Shipping is free, and with the discount, you’re looking at about $750 a pair. Not cheap, but about half the price of what they go for in the US. 

If you haven’t ordered Edward Greens before, know that the general rule of thumb is to go a half size down from your Brannock size. That is, if you normally wear a 10D, then you’re probably a 9.5 in most of Edward Green’s shoes. The only exception is maybe the 888 last, which is tighter at the toe box, so some people take their regular US size. 

How Much Should You Spend on Dress Shoes?
One of the questions I frequently get in my inbox is: “I’m looking to buy a better pair of dress shoes, and only have X to spend. Should I save up for something better, or is so-and-so brand OK?” Like with many questions we get, a lot depends on the person asking.  
It’s worth noting, however, that in footwear (like in everything), there are serious diminishing returns after a certain point. Very roughly speaking, that point tends to be around $350 at full retail, although what’s sold at full retail can be had for less with smart shopping (eBay, factory seconds, seasonal sales, thrift stores, etc).
The Unfortunate Reality of Diminishing Returns
There are a number of things that go into the construction of a good shoe, but the two biggest are: the quality of the leather used and how the soles have been attached. Jesse did a great job in describing the difference between corrected grain and full grain leathers here. It’s also worth noting that even among full-grain leathers, there can be differences in quality. Additionally, most well made shoes will have their shoes attached through a Goodyear or Blake stitching process. Jesse reviewed some of these in the second episode of our video series, and you can read more about each technique here. The short of it is: with a sole that’s been stitched on, rather than glued, you can more easily resole your shoes, which means you don’t have to bin them when the bottoms wear out.
In the past, the “entry price” for good (dress) shoes tended to be around $350. These were usually from Allen Edmonds, Ralph Lauren, and Brooks Brothers, although not everything from these brands were worth buying. There were also some European names such as Herring and Loake’s 1880 line.
After this, you get marginally better constructions, but the differences become smaller and smaller (perhaps a leather insole vs. a fiberboard insole, or a sole that’s been attached by hand rather than machine, or slightly better leathers used for the uppers). Largely, as you move up from the $350 MSRP mark, you’re paying for design. A $1,250 pair of Edward Greens won’t last you 4x longer than a $350 pair from Allen Edmonds, but to many, they’re shaped and finished more handsomely.
The Emergence of a More Competitive Market
The good news is that the market has gotten a lot more competitive in the last five years, and the cost/ benefit curve has smoothed out considerably. Today, there are companies such as Beckett Simonon, John Doe, and Jack Erwin below the $200 price mark (the last of which I was particularly impressed by). Just a hair over $200 is Meermin, which I still think is one of the best values for (relatively) affordable footwear. They have a “Classic” line for about $200 (but with customs and duties, you might pay around $230) and a higher end “Linea Maestro” line for about $300 starting. And at the $350 mark, there’s more than Allen Edmonds and Loake’s 1880 these days. Paul Evans, Kent Wang, and Howard Yount are all good companies to look into.
The question of how much should you spend isn’t about what’s “good” in the footwear market, it’s about what’s “good enough” for you. For dress shoes, the only real criteria are: quality full-grain leather uppers and some kind of stitched on sole. Much of the rest is about aesthetics and personal preference.
(Photo: Crockett & Jones’ Whitehall oxfords at Ben Silver)

How Much Should You Spend on Dress Shoes?

One of the questions I frequently get in my inbox is: “I’m looking to buy a better pair of dress shoes, and only have X to spend. Should I save up for something better, or is so-and-so brand OK?” Like with many questions we get, a lot depends on the person asking. 

It’s worth noting, however, that in footwear (like in everything), there are serious diminishing returns after a certain point. Very roughly speaking, that point tends to be around $350 at full retail, although what’s sold at full retail can be had for less with smart shopping (eBay, factory seconds, seasonal sales, thrift stores, etc).

The Unfortunate Reality of Diminishing Returns

There are a number of things that go into the construction of a good shoe, but the two biggest are: the quality of the leather used and how the soles have been attached. Jesse did a great job in describing the difference between corrected grain and full grain leathers here. It’s also worth noting that even among full-grain leathers, there can be differences in quality. Additionally, most well made shoes will have their shoes attached through a Goodyear or Blake stitching process. Jesse reviewed some of these in the second episode of our video series, and you can read more about each technique here. The short of it is: with a sole that’s been stitched on, rather than glued, you can more easily resole your shoes, which means you don’t have to bin them when the bottoms wear out.

In the past, the “entry price” for good (dress) shoes tended to be around $350. These were usually from Allen Edmonds, Ralph Lauren, and Brooks Brothers, although not everything from these brands were worth buying. There were also some European names such as Herring and Loake’s 1880 line.

After this, you get marginally better constructions, but the differences become smaller and smaller (perhaps a leather insole vs. a fiberboard insole, or a sole that’s been attached by hand rather than machine, or slightly better leathers used for the uppers). Largely, as you move up from the $350 MSRP mark, you’re paying for design. A $1,250 pair of Edward Greens won’t last you 4x longer than a $350 pair from Allen Edmonds, but to many, they’re shaped and finished more handsomely.

The Emergence of a More Competitive Market

The good news is that the market has gotten a lot more competitive in the last five years, and the cost/ benefit curve has smoothed out considerably. Today, there are companies such as Beckett Simonon, John Doe, and Jack Erwin below the $200 price mark (the last of which I was particularly impressed by). Just a hair over $200 is Meermin, which I still think is one of the best values for (relatively) affordable footwear. They have a “Classic” line for about $200 (but with customs and duties, you might pay around $230) and a higher end “Linea Maestro” line for about $300 starting. And at the $350 mark, there’s more than Allen Edmonds and Loake’s 1880 these days. Paul Evans, Kent Wang, and Howard Yount are all good companies to look into.

The question of how much should you spend isn’t about what’s “good” in the footwear market, it’s about what’s “good enough” for you. For dress shoes, the only real criteria are: quality full-grain leather uppers and some kind of stitched on sole. Much of the rest is about aesthetics and personal preference.

(Photo: Crockett & Jones’ Whitehall oxfords at Ben Silver)

Which boots are best for snow?
With most of the United States seeing some early flakeage this year, it’s time to break out the sleet-kickers. Some things to consider if you’re considering new winter boots, whether you need dress boots or something less sleek:
Traction
For minimum slippage on snow and ice, you want an outsole that is relatively soft with maximum tread. Ralph Fabricius of Russell Moccasin told me that you don’t want “a real hard sole for ice—that’s two hard surfaces up against one another. Some Vibram [brand] soles have more forgiveness to them.” So a dress leather sole is right out—adding a Topy rubber sole probably helps a little. The title of grippiest, according to Ralph, goes to Vibram’s Fire and Ice or Olympia soles. My Danner boots (pictured above) use a light but deeply lugged Vibram Kletterlift outsole that suited me well on a trip to Quebec last January. The white Christy wedge sole that looks so darn good with so many boots is not a great choice for snow—too flat and too hard.
For dress boots you’ll find Dainite studded rubber or Ridgeway (also a Dainite product) soles are handy and widely available on better British shoes, especially country boots like those from Crockett and Jones. Likewise Commando lugged soles. On icy sidewalks, though, there’s not much you can do but be cautious.
Water resistance
In cold temperatures, you can often get away with outerwear that’s not 100% waterproof—it will take a lot longer for snow to soak through the shoulders of a heavy wool coat than steady rain. Water from melting snow can start getting into shoes rather quickly, though. Leather is hide, and by definition porous, so you have two options: treat your leather boots with a waterproofing compound like mink oil or Obenauf’s LP, which can darken leather and will need re-proofing over time, or add a layer of synthetic material, like Gore-Tex. Hiking boots—I’m partial to classically styled models like Danners or Merrells—are the most likely to feature a synthetic liner; I don’t know of any true dress boots that do so. Of note is that the highest-end hiking boots, like Limmers, do not use synthetic midlayers, but rather recommend waterproofing treatments.
For dress boots, you’re best off avoiding serious snow and slush if you can, and treating your leather boots well, both before and after you go out in winter conditions. So, rub them down with a quality, natural leather protectant regularly, and once you get out of the snow, wipe them clean, use shoe trees, and let them dry away from heat to avoid cracking or overdrying the leather. Crockett and Jones’s Snowdon model is one of the few dress boots that claim to be waterproof, with a waxy leather upper and Norwegian/Veldtshoen construction that is less likely to let water seep in between the sole and the upper than most shoes. If I had a pair of Snowdons, though, I’d still shovel the walk in something I wouldn’t feel I had to fuss over.
Warmth
Few boots are significantly insulated by themselves. Viberg hikers use a layer of Thinsulate, and you can always wear down booties, I guess. Bean Boots, a classic choice for long New England winters, are really quite cold, although L.L. does offer shearling/Thinsulate lined models. For dress boots, Paul at Leffot recommends Edward Green Galway boots, which can be made to order with a shearling lined shaft. Woah. Let’s see those again. Nice. Like Eddie Green Uggs.
Of course, warm socks provide insulation when boots don’t. Cotton socks are poor insulators when dry and miserable to wear when wet. I’m a big believer in SmartWool’s widely available wool-blend socks. Are they dress socks? No; but if you’re wearing a boot with a high shaft anyway, the dress-appropriateness of your sock becomes less of an issue. If you’re desperate for a little more warmth without resorting to all-out ultra-thick hiking socks, you can add a sock liner, which you wear as sort of a baselayer for your feet. Sock liners (also called liner socks) are usually made from synthetics or silk—quite comfortable and not too thick. One last tip for warm feet: add a layer to your legs. Long underwear under your trousers is too warm for most offices, but if you know you’ll be out in the elements a while, they’re worth it: warmer legs will make your feet feel warmer, too.
-Pete

Which boots are best for snow?

With most of the United States seeing some early flakeage this year, it’s time to break out the sleet-kickers. Some things to consider if you’re considering new winter boots, whether you need dress boots or something less sleek:

Traction

For minimum slippage on snow and ice, you want an outsole that is relatively soft with maximum tread. Ralph Fabricius of Russell Moccasin told me that you don’t want “a real hard sole for ice—that’s two hard surfaces up against one another. Some Vibram [brand] soles have more forgiveness to them.” So a dress leather sole is right out—adding a Topy rubber sole probably helps a little. The title of grippiest, according to Ralph, goes to Vibram’s Fire and Ice or Olympia soles. My Danner boots (pictured above) use a light but deeply lugged Vibram Kletterlift outsole that suited me well on a trip to Quebec last January. The white Christy wedge sole that looks so darn good with so many boots is not a great choice for snow—too flat and too hard.

For dress boots you’ll find Dainite studded rubber or Ridgeway (also a Dainite product) soles are handy and widely available on better British shoes, especially country boots like those from Crockett and Jones. Likewise Commando lugged soles. On icy sidewalks, though, there’s not much you can do but be cautious.

Water resistance

In cold temperatures, you can often get away with outerwear that’s not 100% waterproof—it will take a lot longer for snow to soak through the shoulders of a heavy wool coat than steady rain. Water from melting snow can start getting into shoes rather quickly, though. Leather is hide, and by definition porous, so you have two options: treat your leather boots with a waterproofing compound like mink oil or Obenauf’s LP, which can darken leather and will need re-proofing over time, or add a layer of synthetic material, like Gore-Tex. Hiking boots—I’m partial to classically styled models like Danners or Merrells—are the most likely to feature a synthetic liner; I don’t know of any true dress boots that do so. Of note is that the highest-end hiking boots, like Limmers, do not use synthetic midlayers, but rather recommend waterproofing treatments.

For dress boots, you’re best off avoiding serious snow and slush if you can, and treating your leather boots well, both before and after you go out in winter conditions. So, rub them down with a quality, natural leather protectant regularly, and once you get out of the snow, wipe them clean, use shoe trees, and let them dry away from heat to avoid cracking or overdrying the leather. Crockett and Jones’s Snowdon model is one of the few dress boots that claim to be waterproof, with a waxy leather upper and Norwegian/Veldtshoen construction that is less likely to let water seep in between the sole and the upper than most shoes. If I had a pair of Snowdons, though, I’d still shovel the walk in something I wouldn’t feel I had to fuss over.

Warmth

Few boots are significantly insulated by themselves. Viberg hikers use a layer of Thinsulate, and you can always wear down booties, I guess. Bean Boots, a classic choice for long New England winters, are really quite cold, although L.L. does offer shearling/Thinsulate lined models. For dress boots, Paul at Leffot recommends Edward Green Galway boots, which can be made to order with a shearling lined shaft. Woah. Let’s see those again. Nice. Like Eddie Green Uggs.

Of course, warm socks provide insulation when boots don’t. Cotton socks are poor insulators when dry and miserable to wear when wet. I’m a big believer in SmartWool’s widely available wool-blend socks. Are they dress socks? No; but if you’re wearing a boot with a high shaft anyway, the dress-appropriateness of your sock becomes less of an issue. If you’re desperate for a little more warmth without resorting to all-out ultra-thick hiking socks, you can add a sock liner, which you wear as sort of a baselayer for your feet. Sock liners (also called liner socks) are usually made from synthetics or silk—quite comfortable and not too thick. One last tip for warm feet: add a layer to your legs. Long underwear under your trousers is too warm for most offices, but if you know you’ll be out in the elements a while, they’re worth it: warmer legs will make your feet feel warmer, too.

-Pete

It’s On Sale: Edward Green Shoes

For our readers in England, Edward Green is holding a sale this Saturday from 8am until 2pm. Shoes will be discounted by 60%, with a limit of five purchases per customer. You can check out the sale at Cliftonville Road, Northampton, NN1 5BU.  

And if you’re wondering, no, they won’t do phone orders. Trust me, I’ve tried. 

Chelsea Boots
For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first kinds of boots I fell in love with were Chelseas. Chelseas are a kind of ankle-length, pull-on boot with elastic side gussets. They were invented in the mid-19th century as an alternative to the button boot, but they didn’t really gain popularity until the 1960s, when they were picked up by young men in Chelsea, London (hence the name) and then famously worn by The Beatles (though technically speaking, the Beatles wore a modified version of the Chelsea).
Various English shoe companies make Chelseas in their most classic form (the kind that we associate with the Mod movement of the 1960s). On the uppermost end, there’s Edward Green’s Newmarket, which are fantastically beautiful, but also fantastically expensive. A bit more affordable (but still quite expensive) is Crockett & Jones. They have three versions, simply named models 3, 5, and 8. Their Chelsea 3, being the sleekest and featuring a single-layer leather sole, is the dressiest. Models 5 and 8, on the other hand, are built on studded Dainite soles, with number 8 being a nice, almond-toe compromise between the sleekness of number 3 and the roundness of 5. You can buy these from Crockett & Jones or Barneys New York, though Pediwear, Robert Old, and P. Lal will likely have better prices (note, P. Lal’s prices are denoted in Malaysian ringgit, so you have to convert them).
Slightly more affordable options can be had through Grenson, Shipton & Heneage, and Carmina. Our friends at The Armoury stock the Carmina version in the very sleek Simpson last, while Skoaktiebolaget sells them in the slightly less tapered Rain (a last, as many readers know, is the form that the shoe’s leather is pulled over, and is what determines the shoe’s shape). Carmina can also custom make Chelseas for you, where you choose the last and material, but this comes at a 50% upcharge.
For something more affordable still, there’s Loake and Herring, Charles Tyrwhitt (don’t be fooled by the sale, as they’re always on sale), Markowski, and RM Williams. You can also check eBay, although you’ll want to be careful to avoid the frumpy versions (I’m not a fan of Blundstones, though my friend Jake over at Wax Wane likes them).
If you’re considering getting a pair, try them in black. Those are arguably the easiest and most versatile to wear. If shaped right, and built on a leather sole, they could span everything from suits to jeans. Brown leather would also work well, although on the suit end, they might need to be paired with more casual options (Mark over at The Armoury can be seen here looking great in his tan suit, blue gingham shirt, and Gaziano & Girling Chelseas). Brown suede could also be nice, especially under a pair of tan cavalry twill trousers or some light, washed blue jeans. Whatever you choose, I recommend wearing them with a slim trouser leg, just to keep with the Mod tradition.

Chelsea Boots

For as long as I’ve been interested in shoes, I’ve always favored boots, and one of the first kinds of boots I fell in love with were Chelseas. Chelseas are a kind of ankle-length, pull-on boot with elastic side gussets. They were invented in the mid-19th century as an alternative to the button boot, but they didn’t really gain popularity until the 1960s, when they were picked up by young men in Chelsea, London (hence the name) and then famously worn by The Beatles (though technically speaking, the Beatles wore a modified version of the Chelsea).

Various English shoe companies make Chelseas in their most classic form (the kind that we associate with the Mod movement of the 1960s). On the uppermost end, there’s Edward Green’s Newmarket, which are fantastically beautiful, but also fantastically expensive. A bit more affordable (but still quite expensive) is Crockett & Jones. They have three versions, simply named models 3, 5, and 8. Their Chelsea 3, being the sleekest and featuring a single-layer leather sole, is the dressiest. Models 5 and 8, on the other hand, are built on studded Dainite soles, with number 8 being a nice, almond-toe compromise between the sleekness of number 3 and the roundness of 5. You can buy these from Crockett & Jones or Barneys New York, though Pediwear, Robert Old, and P. Lal will likely have better prices (note, P. Lal’s prices are denoted in Malaysian ringgit, so you have to convert them).

Slightly more affordable options can be had through Grenson, Shipton & Heneage, and Carmina. Our friends at The Armoury stock the Carmina version in the very sleek Simpson last, while Skoaktiebolaget sells them in the slightly less tapered Rain (a last, as many readers know, is the form that the shoe’s leather is pulled over, and is what determines the shoe’s shape). Carmina can also custom make Chelseas for you, where you choose the last and material, but this comes at a 50% upcharge.

For something more affordable still, there’s Loake and Herring, Charles Tyrwhitt (don’t be fooled by the sale, as they’re always on sale), Markowski, and RM Williams. You can also check eBay, although you’ll want to be careful to avoid the frumpy versions (I’m not a fan of Blundstones, though my friend Jake over at Wax Wane likes them).

If you’re considering getting a pair, try them in black. Those are arguably the easiest and most versatile to wear. If shaped right, and built on a leather sole, they could span everything from suits to jeans. Brown leather would also work well, although on the suit end, they might need to be paired with more casual options (Mark over at The Armoury can be seen here looking great in his tan suit, blue gingham shirt, and Gaziano & Girling Chelseas). Brown suede could also be nice, especially under a pair of tan cavalry twill trousers or some light, washed blue jeans. Whatever you choose, I recommend wearing them with a slim trouser leg, just to keep with the Mod tradition.

Shoe Terminology

Yesterday’s post on shoe construction seemed to be popular, so I thought I’d do something similar by going through some more terminology. Pictured above are three of my favorite shoes, with some labeling of their different parts. Click each photo to enlarge them.

Aglet: A small plastic or metal sheath used to protect the end of a shoestring, cord, or drawstring. 

Apron: Some sort of visible stitching or edge that forms a sort of “lake” at the front of the shoe. You typically only see this on derbys or loafers.

Blind Eyelet: See eyelets.

Brogueing: The small perforations and small punches used to decorate a shoe. It’s been said that these were historically done to help country shoes drain out water, but nowadays it’s just for decoration.

Burnishing: A bit of darkening of the leather, usually at the toe or heel. Sometimes it’s called antiquing, especially if it’s done all over the shoe.

Eyelets: The holes through which you stick your shoelaces. Metal rings called grommets are usually used to support these holes. If the grommets are on the exposed side of the leather - the side that you can see - and they’re in a different color than your uppers, then they’re called agatine eyelets. If they match your uppers, they’re called matched agatine, and if they’re on the underside of the leather, they’re called blind eyelets. Generally speaking, blind eyelets are more formal than matched agatine eyelets, which in turn are more formal than agatine. Essentially, the less visible the grommets, the more formal the shoe.

Eyelet tabs: The tabs on a derby that are used to hold eyelets.

Heel cup: A strip of leather on the outside of the heel used to cover the seam joining the quarters.

Heel lifts: Two to four pieces of leather stacked to form a heel. The sides are then usually painted black or brown, depending on the color of the upper.

Insole: The layer of the sole that goes on top of the outsole and midsole. This is what the bottom of your feet touches when you wear your shoes.

Instep: The area of the foot between the toes and the ankle. Much of this is covered by the shoe’s vamp and tongue.

Lining: Most leather shoes have a leather lining that helps the shoe maintain its overall shape. You can see the lining here, and read about unlined shoes here

Medallion: An ornamental detail at the toe created by punching or perforating the leather.

Outsole: The exposed part of the sole that actually touches the ground.

Pinking: Zig-zag edges on leather, done for decoration. Sometimes this is called gimping because a shoemaker does this with a gimping machine, in which steel tools with various patterns can be fitted to achieve the desired effect.

Quarter: The part of the upper that starts at about the instep and goes back towards the heel. Every shoe will have two quarters - the parts that cover the inner and outer sides of the foot.

Quarter rubber: A hard, non-slip piece of rubber that’s inserted into the top piece of the heel. Sometimes it’s protected by plastic “heel protectors,” which a cobbler can put in for you.

Scalloping: Like pinking, but instead of a saw-toothed edge, you’ll see a wavy cut.

Sock: A small piece of leather used to hide the nails that keep the sole together. A sock can be full length, three-quarters, or just cover the heel section. The last is most common.

Sole: The entire part of the shoe that’s below the wearer’s foot. These can be single or double leather, or even HAF (double tapering to a single). The upper and sole make up the whole of the shoe.

Throat: The central part of the vamp that dictates the maximum girth of a shoe. The throatline is the seam that joins the rear part of the vamp to the front part of the quarter.

Toe cap: A piece of leather that covers the toe area of a shoe.

Tongue: The piece of leather that comes between your foot and the shoelaces. When I was a kid, we used to pump these to make our shoes inflate, because it was somehow believed that inflatable shoes would increase our athletic performance.

Topline: The opening of the shoe, where you’d stick your foot in. On athletic shoes, this area is typically padded and referred to as the collar. On women’s shoes, you’ll sometimes see the top most part of the topline decorated with a thin, rolled piece of leather (usually in a contrasting color to the upper). That’s called French binding.

Top piece: The part of the heel lift that actually comes in contact with the ground.

Upper: The part of the shoe that you see that’s above the sole. The upper and sole make up the whole of the shoe.

Vamp: If you take a bird’s eye view of your shoe, this is the center front part of the upper.

Waist: The area of the shoe that supports the mid-section of your foot, where your arch is.

Welt: A strip of material that holds the upper, insole, and sole together. Here we see the welt seam, though it’s important to note that just because you see stitching here doesn’t always mean the shoe has been welted. Sometimes stitches are glued here for decorative purposes.

(Shoes pictured: Edward Green Malvern in Chestnut Antique calf, 202 last; Edward Green Dover in Dark Oak antique calf, 606 last; Meermin Linea Maestro plain toe blucher in dark brown Annonay naturacalf, Hiro last)