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.

Totokaelo Man Sale

A store I’ve been really digging lately for casualwear, Totokaelo Man, just did another round of price drops in their sale section. Some items that caught my eye included:

  • An APC striped sweater for $82.25 (I picked up one this season, and think it would make for a nice layering piece this fall)
  • Twins for Peace leather sneakers in white and black for $61.25 (I’ve never handled these in person, but they seem like they could be a nice alternative to pricier options)
  • Twins for Peace canvas sneakers in navy and white for $42
  • Grenson suede crepe soled chukkas for $140.
  • APC Chelsea boots for $180.25 (would look great with a pair of slim jeans or chinos)
  • Margiela chukkas and sidezip boots and for $311 and $344, respectively (a bit more fashion forward, but I think they’d look good with the right ensemble)

You can see what else they have here

Q & Answer: What Shoes Should I Bring On Vacation?

Ben writes: This May, my wife and I are honeymooning in Europe for two weeks. I know that I will be doing a heavy amount of walking. Do you have any suggestions for footwear that will allow me to keep pace with my wife without looking like the ugly American?

Packing shoes for a trip - especially one that requires more than one level of formality - is always tough. When I travel, I fight not to bring more than two pairs of shoes, with one of those pairs on my feet. I don’t always win the fight.

I’ve got plenty of dress shoes that are perfectly comfortable, but none that I’d want to walk miles in. So if I’m bringing a pair of dress shoes to make a big presentation or what-have-you, I’m usually looking to compliment them with a “walking shoe.”

Depending on the season and context, that usually boils down to one of two things: a simple sneaker, or a comfortable boot.

I actually own the Grenson chukka boots pictured above, in a slightly darker brown. I find they work great with jeans or khakis, though I obviously wouldn’t wear them with shorts were I headed somewhere hot. In fact, they’re sort of a three-season shoe - fine anytime but summer. Sometimes I’ll substitute the chunkier, hardier Alden Indy Boot for these. Most importantly, I can put in a few miles on these, and be happy to see them the next day.

I also frequently bring sneakers on trips that will involve walking. As usual, I’d say the simpler the better. Above are a classic, the Adidas Samba. I usually wear Common Projects, which are great but expensive. I’m hoping Kent Wang gets in a full size run of his plain white sneaks soon. And of course if it’s summer, there’s stuff like Jack Purcells and Supergas, among others.

Traveling’s really an exercise in building a capsule wardrobe. You want to carry as few pieces as possible, and have as much interchangability as possible. So: keep it simple, and you’ll be fine.

Q and Answer: Ten In-Between Shoes

Matt asks: I need a new pair of shoes!  What I have right now is either too casual (a sneaker) or too formal (a fancy dress shoe), but I’m trying to figure out something in between. Any suggestions?

This is a question we get a lot. For men who want to wear something a little more put-together than their beat-up Nikes, but aren’t yet ready for a full-on sportcoat-trousers-dress-shoes ensemble, is there anything in between?

The simple answer is: yes. Here are ten choices for casual footwear that will keep you a head above the dirty sneaker crowd. (It’s a little tougher in the summer, so I’ll start there - the pictures run left to right and top to bottom.)

  1. Refined sneakers. When choosing sneakers, look for simplicity. White’s a great color for spring and summer, black and brown will do you well in the cooler months. You want as few details as possible here, and if you’re going to try and dress them up, they should be clean and sharp. I’ve got some Common Projects, the gold standard for this kind of thing, pictured above, but if you can find similarly simple leather sneakers from a brand that doesn’t cost a bajillion dollars, go for it.
  2. Boat shoes. While their ubiquity the past few years or their inherent preppiness might be a turn-off, boat shoes remain the default casual summer shoe (non-sneaker category). Wear them without socks in pretty much any casual situation during the hot-weather months. Then put them away.
  3. Espadrilles. These are the classic European vacation shoe - what Cary Grant might wear to the French Riviera. They’re cheap, comfortable and refined. Just don’t try to wear them outside of summer vacation, and for goodness’ sake don’t wear those awful Toms.
  4. Crepe-soled Chukkas. Desert boots are a comfortable, good-looking mostly-casual shoe for nine months of the year. Like boat shoes, they’re starting to overwhelm with their ubiquity, but if you try an alternative style like the calf version above, you can get a little more refinement and a little less “been there, done that.” (I can’t believe I just typed “been there, done that.”)
  5. Leather-soled Chukkas. Chukkas with leather or dainite soles like the brown suede pair above are one of the most versatile shoes you can own. They’re great with jeans, and in a pinch they could even be worn with a suit (though maybe not in suede). 
  6. Camp Mocs. Camp mocs are the cool-weather equivalent of the boat shoe. Inexpensive, casual, preppy and a little more refined than sneakers. The LL Bean Blucher Moc is the standard here, though the quality isn’t as high on them as it once was. Works great with jeans or chinos, but not so much with a more formal look.
  7. Plain-Toe Bluchers. This is the classic casual shoe. My own pair is an old double-soled pair of Florsheims in shell cordovan. I wear them with everything short of a suit. Black looks like security guard shoes, so avoid it. Brown is a touch more casual than burgundy, and crepe soles a touch more casual than leather.
  8. Country Brogues. Grenson is the classic maker of real country brogues, so that’s what you see above. The leather in shoes was originally perforated by folks who lived in marshy, wet conditions and wanted shoes that shed water. It’s purely decorative now, but still casual relative to other oxfords. If you want to wear brogues casually, look for prominent broguing, a stout shape and heavy soles. These are too casual for most suits (save country suits like corduroy or tweed), but if they’re clunky enough, they can stand up to blue jeans well. The boot equivalent of these shoes is even more casual. Note, also, that crepe soles or (especially) suede can turn down the formality of most dress shoes.
  9. Work and Outdoor Boots. There are a broad range of work-style boots. I’ve pictured something in the middle, the Red Wing Gentleman Traveler. On the casual end are hunting and hiking boots (like Danners) and real work boots (like traditional Red Wings, with lug soles and moc toes). I love my Alden Indy Boots, which are moc-toed, but otherwise quite refined - I wear them with chinos or jeans and a casual blazer all the time. Also in this category are military-inspired boots, like Polo Rangers.
  10. The Chelsea Boot. I’ve pictured a pair by the Australian maker R.M. Williams. A hefty, chunky Chelsea like these is more casual. A more refined model can even be worn with a suit. In fact, the Chelsea is probably the shoe that most comfortably goes from casual to formal.

Remember: city is more formal than country. Leather soles more formal than rubber (and lug soles the least formal of all). Smooth leather is more formal than textured, which is more formal than suede, which in turn is more formal than unpolished. Shoes are more formal than boots. Shapely is more formal than clunky.

And always, always stay away from hybrids. Nothing good can come of two shoes mating.

Finding a level of formality that’s between slovenliness and traditional business dress is vital for anyone who isn’t a slob or a traditional businessman. Hopefully this will set you on your way.

The “Steals & Deals” section of The Rider Boot Co.’s store has some really excellent stuff at the moment, at really excellent prices. Rider’s own designs are sometimes a bit nutty, but there are some attractive choices, too. Perhaps most notable is a modest selection of Grenson shoes, made to a very high standard for a men’s retailer whose name rhymes with Stall Puart - all for less than $200 a pair. Get in on the fun here.

The “Steals & Deals” section of The Rider Boot Co.’s store has some really excellent stuff at the moment, at really excellent prices. Rider’s own designs are sometimes a bit nutty, but there are some attractive choices, too. Perhaps most notable is a modest selection of Grenson shoes, made to a very high standard for a men’s retailer whose name rhymes with Stall Puart - all for less than $200 a pair. Get in on the fun here.

Put This On Episode 5: Clothing Credits

Intro:
Tie: Pierrepont Hicks
Shirt: Lands’ End
Sweater: Vintage Scottish Cashmere
Jeans: Levis LVC 1947
Shoes: Grenson
Vest: Lands’ End

At J. Press:
Shirt: CEGO Custom Shirtmaker
Jacket: Polo Ralph Lauren
Sweater: Vintage Scottish Cashmere
Tie: Vintage Unlabeled
Pocket Square: Luciano Barbera
Pants: Incotex

At Thom Browne:
Shirt: Brooks Brothers Black Fleece
Tie: Santoni
Pocket Square: Vintage
Pants: Vintage Ralph Lauren Purple Label
Shoes: Vintage Florsheim
Socks: Robert Talbott

Gilt Man is offering Grenson shoes for the first time in a while today. It’s one of the only high-quality shoe brands they offer. A lot will likely be from Grenson’s lower-end lines, but even those are solid for the price. These are English-made country shoes, excellent for casual wear. Starts at 9AM pacific, noon eastern. (Note that they are listed by their UK sizes.)

Gilt Man is offering Grenson shoes for the first time in a while today. It’s one of the only high-quality shoe brands they offer. A lot will likely be from Grenson’s lower-end lines, but even those are solid for the price. These are English-made country shoes, excellent for casual wear. Starts at 9AM pacific, noon eastern. (Note that they are listed by their UK sizes.)

It’s On eBay
Paul Stuart (by Grenson) Loafers (11C)
Start at $9.99 or BIN $79.99

It’s On eBay

Paul Stuart (by Grenson) Loafers (11C)

Start at $9.99 or BIN $79.99

It’s On Ebay
Grenson Chukkas in Navy
Starting at about $130, ends January 16

It’s On Ebay

Grenson Chukkas in Navy

Starting at about $130, ends January 16

Pictured: the Grenson Archie in Chestnut.
Double-soled and bulbous, but beautiful.  This is about as casual as what we’d call a dress shoe can get.  Double soled.  Heavily brogued (broguing is the punch-hole decoration), brown, and fat.
But wouldn’t this look lovely with jeans?  Or with odd trousers with a big two inch cuff?  Or corduroys?  The heft of this shoe stands up to denim, which is unusual for a dress shoe.  The double soles and Goodyear welting mean that they’ll last a lifetime, as well.
One note: if you don’t feel like paying full freight, Grenson seconds do come up from time to time on Ebay, so keep your eyes peeled (and your US-to-UK size converter handy).
(via Men’s Flair)

Pictured: the Grenson Archie in Chestnut.

Double-soled and bulbous, but beautiful.  This is about as casual as what we’d call a dress shoe can get.  Double soled.  Heavily brogued (broguing is the punch-hole decoration), brown, and fat.

But wouldn’t this look lovely with jeans?  Or with odd trousers with a big two inch cuff?  Or corduroys?  The heft of this shoe stands up to denim, which is unusual for a dress shoe.  The double soles and Goodyear welting mean that they’ll last a lifetime, as well.

One note: if you don’t feel like paying full freight, Grenson seconds do come up from time to time on Ebay, so keep your eyes peeled (and your US-to-UK size converter handy).

(via Men’s Flair)