Q and Answer: Can I Wear Loafers With A Suit?
A loyal reader asks: Can I wear loafers with a suit? I rarely see it done on blogs.
Yes you can. But should you? That’s more complicated.
The loafer, especially the American penny loafer, was created to be a casual shoe. The simple fact that it slipped on and off made it the 1935 equivalent of those socks with treads printed onto them. Over the years, though, that’s softened, at least here in the States.
Today, there are a few kinds of men wearing loafers with suits.
Men in hip, casual suits. Search loafers and suit on the web and you’ll find plenty of young men in cotton suits, fashion-y suits and the like who look fine with loafers. Not necessarily great, there’s still something a bit dissonant about it, but fine. Going out at night in a dark suit, no tie and loafers is perfectly OK with me, if it’s your preference.
All-American Businessman types, who wear penny loafers with business suits because… well… they don’t want to lace up their shoes? Or something? This has become traditional for Americans, but it isn’t very good looking, is borderline shocking to some non-Americans, and just generally makes you look like a yokel. Don’t do this.
Wall Street types. Not just folks who work on Wall Street, but folks who aspire to be the star of the movie “Wall Street.” Or perhaps “The Wolf of Wall Street.” These people are awful. Don’t be one of them.
The upshot? Most of the time, you should avoid wearing loafers with suits. Your Weejuns are much more at home with flannel trousers or corduroys anyway. If you’re headed to a Suit Occasion, wear a pair of shoes you have to lace. It’s the least you can do.
(And that goes for you too, Dave.)

Q and Answer: Can I Wear Loafers With A Suit?

A loyal reader asks: Can I wear loafers with a suit? I rarely see it done on blogs.

Yes you can. But should you? That’s more complicated.

The loafer, especially the American penny loafer, was created to be a casual shoe. The simple fact that it slipped on and off made it the 1935 equivalent of those socks with treads printed onto them. Over the years, though, that’s softened, at least here in the States.

Today, there are a few kinds of men wearing loafers with suits.

  • Men in hip, casual suits. Search loafers and suit on the web and you’ll find plenty of young men in cotton suits, fashion-y suits and the like who look fine with loafers. Not necessarily great, there’s still something a bit dissonant about it, but fine. Going out at night in a dark suit, no tie and loafers is perfectly OK with me, if it’s your preference.
  • All-American Businessman types, who wear penny loafers with business suits because… well… they don’t want to lace up their shoes? Or something? This has become traditional for Americans, but it isn’t very good looking, is borderline shocking to some non-Americans, and just generally makes you look like a yokel. Don’t do this.
  • Wall Street types. Not just folks who work on Wall Street, but folks who aspire to be the star of the movie “Wall Street.” Or perhaps “The Wolf of Wall Street.” These people are awful. Don’t be one of them.

The upshot? Most of the time, you should avoid wearing loafers with suits. Your Weejuns are much more at home with flannel trousers or corduroys anyway. If you’re headed to a Suit Occasion, wear a pair of shoes you have to lace. It’s the least you can do.

(And that goes for you too, Dave.)

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.”

"In the 1930s there was this tendency in Hollywood to portray everyone as rich. Even if they were doing a poor man’s dance, they were all so nicely clothed, gowned, coiffured. That’s why I decided to wear white socks, loafers, T-shirts, and blue jeans."  —Gene Kelly
White socks, though?
-Pete

"In the 1930s there was this tendency in Hollywood to portray everyone as rich. Even if they were doing a poor man’s dance, they were all so nicely clothed, gowned, coiffured. That’s why I decided to wear white socks, loafers, T-shirts, and blue jeans."  —Gene Kelly

White socks, though?

-Pete

(Source: interviewmagazine.com)

Time to Reconsider Black Shoes
Black shoes have been tagged for years with the stigma of the duckbilled, corrected grain kicks that crawled out of the menswear dark ages of the 1990s and dominated business wear in the early 2000s. Ditching anatomically confusing and unappealingly dull shoes for the universe of brown or burgundy choices made on more traditional, rounder lasts has become a rite of passage for guys who decide to put a little thought into what they wear. But in shunning black shoes (except for formal and business formal wear), we’re missing out on one of modernity’s favorite colors.
Wearing black shoes in a nonstandard texture—scotch grain or even suede—makes sure they won’t be confused for interview shoes. The Tricker’s pictured are in black alpine grain (another word for scotch grain or pebble grain) and sit on a Dainite rubber sole. Although there’s some DNA shared with the classic American business wingtip, these are more closely related to English country shoes. The market for those old American wingtips, like vintage Florsheim Imperials, has gotten more competitive, so they’re not the value they used to be, but still a strong option. Finding a shoe with a natural midsole can ease you into blackshoes if you don’t want to go full murdered out.  On the other end of the spectrum would be something like a snaffle bit loafer, an undeservedly stigmatized shape. George Hamilton embraces their loucheness; I’d wear them with washed jeans and a small cuff.
While gray wool fabrics are maybe the most natural complement for black shoes (see Thom Browne), navy is another easy match for more formal dress, and tans, olives, and blue denim work for no-jacket-required wear, provided the cut is right (bigger shoes? bigger pant hem, generally). To state the obvious, black also goes with black (some designers and writers have made entire careers out of it), but different black tones can have varying undertones of green or red, and can in fact clash.
-Pete

Time to Reconsider Black Shoes

Black shoes have been tagged for years with the stigma of the duckbilled, corrected grain kicks that crawled out of the menswear dark ages of the 1990s and dominated business wear in the early 2000s. Ditching anatomically confusing and unappealingly dull shoes for the universe of brown or burgundy choices made on more traditional, rounder lasts has become a rite of passage for guys who decide to put a little thought into what they wear. But in shunning black shoes (except for formal and business formal wear), we’re missing out on one of modernity’s favorite colors.

Wearing black shoes in a nonstandard texturescotch grain or even suedemakes sure they won’t be confused for interview shoes. The Tricker’s pictured are in black alpine grain (another word for scotch grain or pebble grain) and sit on a Dainite rubber sole. Although there’s some DNA shared with the classic American business wingtip, these are more closely related to English country shoes. The market for those old American wingtips, like vintage Florsheim Imperials, has gotten more competitive, so they’re not the value they used to be, but still a strong option. Finding a shoe with a natural midsole can ease you into blackshoes if you don’t want to go full murdered out.  On the other end of the spectrum would be something like a snaffle bit loafer, an undeservedly stigmatized shape. George Hamilton embraces their loucheness; I’d wear them with washed jeans and a small cuff.

While gray wool fabrics are maybe the most natural complement for black shoes (see Thom Browne), navy is another easy match for more formal dress, and tans, olives, and blue denim work for no-jacket-required wear, provided the cut is right (bigger shoes? bigger pant hem, generally). To state the obvious, black also goes with black (some designers and writers have made entire careers out of it), but different black tones can have varying undertones of green or red, and can in fact clash.

-Pete

Floppy Shoes
I love floppy shoes, particularly for wearing on warm weather days. By floppy, I mean what’s usually referred to as unlined - a term that’s kind of a misnomer since few shoes are truly made without any lining. Like with neckties, when a company describes their shoes as unlined, what they usually mean is that they’re partially or lightly lined, as some lining is often still used to give the shoes some structure. 
To explain, a well-made pair of leather shoes will usually have a full leather sock liner built in. That means two pieces of leather are joined together to form the upper. There’s the leather that faces the outside world, and the leather that touches your feet. By joining these two pieces together, you get something that has a bit more structure and will holds its shape better. Without the lining, however, you get a softer, more comfortable shoe. Whereas most leather shoes need a break-in period, unlined shoes will feel like slippers on first wear. 
My own floppy unlined shoes are by Alden. I have two pairs of their suede chukkas – one in snuff suede and the other in tan. The bottom is built on Alden’s flex welt sole, which is a thin, water-locked, oiled leather. It’s exceptionally flexible and complements the shoes’ unlined construction well. The combination of the two makes for a lightweight, comfortable boot that looks as great with jeans and chinos as they do with grey wool trousers.
They’re expensive at full retail, but sometimes you can find them for about half off on eBay. Allen Edmonds has a similar model called the Amok. The shape is slightly sleeker, and it comes in at $250. Nordstorm describes it as having a leather lining, but you can see this isn’t true when you zoom in on the photos.
Alden also makes unlined derbys and loafers, which you can find through Harrison, Unionmade, Leffot, and Shoemart. The unlined loafers also come in shell cordovan (most notably in the well-beloved Horween #8, which has a beautiful reddish-brown color). That one is sold exclusively through Brooks Brothers, who has them on discount today as part of their Corporate Card event (30% off for anyone who holds a Brooks corporate card). For something a bit more affordable – but no less well made – consider Rancourt. They have a made-to-order system that can allow you to order any of their shoes unlined. I’m personally thinking of getting some snuff suede unlined penny loafers from them in the next month or so. 
(Photo credit: Unionmade)

Floppy Shoes

I love floppy shoes, particularly for wearing on warm weather days. By floppy, I mean what’s usually referred to as unlined - a term that’s kind of a misnomer since few shoes are truly made without any lining. Like with neckties, when a company describes their shoes as unlined, what they usually mean is that they’re partially or lightly lined, as some lining is often still used to give the shoes some structure. 

To explain, a well-made pair of leather shoes will usually have a full leather sock liner built in. That means two pieces of leather are joined together to form the upper. There’s the leather that faces the outside world, and the leather that touches your feet. By joining these two pieces together, you get something that has a bit more structure and will holds its shape better. Without the lining, however, you get a softer, more comfortable shoe. Whereas most leather shoes need a break-in period, unlined shoes will feel like slippers on first wear. 

My own floppy unlined shoes are by Alden. I have two pairs of their suede chukkas – one in snuff suede and the other in tan. The bottom is built on Alden’s flex welt sole, which is a thin, water-locked, oiled leather. It’s exceptionally flexible and complements the shoes’ unlined construction well. The combination of the two makes for a lightweight, comfortable boot that looks as great with jeans and chinos as they do with grey wool trousers.

They’re expensive at full retail, but sometimes you can find them for about half off on eBay. Allen Edmonds has a similar model called the Amok. The shape is slightly sleeker, and it comes in at $250. Nordstorm describes it as having a leather lining, but you can see this isn’t true when you zoom in on the photos.

Alden also makes unlined derbys and loafers, which you can find through Harrison, Unionmade, Leffot, and Shoemart. The unlined loafers also come in shell cordovan (most notably in the well-beloved Horween #8, which has a beautiful reddish-brown color). That one is sold exclusively through Brooks Brothers, who has them on discount today as part of their Corporate Card event (30% off for anyone who holds a Brooks corporate card). For something a bit more affordable – but no less well made – consider Rancourt. They have a made-to-order system that can allow you to order any of their shoes unlined. I’m personally thinking of getting some snuff suede unlined penny loafers from them in the next month or so. 

(Photo credit: Unionmade)

The Charm of Tassel Loafers
I really like tassel loafers. I’m wearing a shell cordovan pair now with brown sharkskin trousers, a dark green v-neck sweater, light blue oxford cloth button-down shirt, navy over-the-calf socks, and a dark reddish-brown alligator belt. With clothes that are a bit too fully cut, tassel loafers can look a little fuddy duddy; with clothes that are too tight, they can look overly hip. Somewhere in the middle, I think, is where they look best.
Tassel loafers came into being in the post-war period of the 1940s, right when tweed jackets, Shetland sweaters, and penny loafers dominated prep schools and Ivy League campuses. As college students graduated, they wanted something as comfortable as their slip-ons, but were a bit dressier and more sophisticated for their new life in the business world. It was around this time that an actor named Paul Lukas came back from Europe with a pair of oxfords. They had little tassels at the end of their laces, which Lukas thought made them look more lively. So he took them to a couple of New York shoemakers to see if they could make something similar, and they in turn took the job to Alden. The company’s president at the time, Arthur Tarlow, came up with tasseled loafers and they were an instant success. That makes Alden’s model the original, and Paul Lukas the first man to wear this style of footwear. You can read more about this wonderful history in this article by Bruce Boyer.
Tassel loafers come in a variety of colors and leathers. The most common is brown calfskin, but the ne plus ultra is the reddish-brown shell cordovan that comes from Chicago’s Horween Tannery. Shell cordovan has the particularly good quality of holding the color burgundy well. In calf, burgundy can sometimes look cheap, but in horsehide leather, it absolutely glows. 
As for where to get them, there are probably a dozens of versions on the market. I’ll only cover a few. As mentioned, Alden’s is the original and its history as the classic makes it hard to beat. They also make a similar model for Brooks Brothers. The main deviation is the piece of leather that’s added to the heel cup. From England, we have Crockett & Jones’ Cavendish and Edward Green’s Belgravia. Crockett & Jones also makes a shell cordovan version for Ralph Lauren called the the Marlow, and it has a slightly more unique shade of shell cordovan brown.
My own pair is Allen Edmonds’ Grayson. It’s quite similar to Alden’s, but it has a higher vamp, which is the part the shoe that covers the top part of your foot. I thought it looked slightly better this way, so I bought a pair in shell cordovan. I couldn’t be happier with the purchase and recommend them highly.
If you’d like more affordable options, consider Loake’s Lincoln and Meermin’s 101381. Both come in around $175, but Meermin has the added advantage of being able to do special orders. If you’d like to get a pair in shell cordovan or suede, or made from a different last or sole, they’d be happy to make you a pair for a small surcharge. I have a pair of their made-to-order shoes and couldn’t be more impressed with their value. To order, read this buyer’s guide and then go to Meermin’s website. My only comment on that guide is that you should ask Meermin for sizing advice; don’t just assume. 
Tassel loafers aren’t anything I’d call “an essential,” but they’re certainly very enjoyable to wear. If you work in an environment that lets you get away with more casual footwear, try wearing a pair of these with a wool sweater and corduroys, or maybe a checkered tweed and flannel wool trousers. Both will carry a great sense of American style that’s both casual and sophisticated. 

The Charm of Tassel Loafers

I really like tassel loafers. I’m wearing a shell cordovan pair now with brown sharkskin trousers, a dark green v-neck sweater, light blue oxford cloth button-down shirt, navy over-the-calf socks, and a dark reddish-brown alligator belt. With clothes that are a bit too fully cut, tassel loafers can look a little fuddy duddy; with clothes that are too tight, they can look overly hip. Somewhere in the middle, I think, is where they look best.

Tassel loafers came into being in the post-war period of the 1940s, right when tweed jackets, Shetland sweaters, and penny loafers dominated prep schools and Ivy League campuses. As college students graduated, they wanted something as comfortable as their slip-ons, but were a bit dressier and more sophisticated for their new life in the business world. It was around this time that an actor named Paul Lukas came back from Europe with a pair of oxfords. They had little tassels at the end of their laces, which Lukas thought made them look more lively. So he took them to a couple of New York shoemakers to see if they could make something similar, and they in turn took the job to Alden. The company’s president at the time, Arthur Tarlow, came up with tasseled loafers and they were an instant success. That makes Alden’s model the original, and Paul Lukas the first man to wear this style of footwear. You can read more about this wonderful history in this article by Bruce Boyer.

Tassel loafers come in a variety of colors and leathers. The most common is brown calfskin, but the ne plus ultra is the reddish-brown shell cordovan that comes from Chicago’s Horween Tannery. Shell cordovan has the particularly good quality of holding the color burgundy well. In calf, burgundy can sometimes look cheap, but in horsehide leather, it absolutely glows. 

As for where to get them, there are probably a dozens of versions on the market. I’ll only cover a few. As mentioned, Alden’s is the original and its history as the classic makes it hard to beat. They also make a similar model for Brooks Brothers. The main deviation is the piece of leather that’s added to the heel cup. From England, we have Crockett & Jones’ Cavendish and Edward Green’s Belgravia. Crockett & Jones also makes a shell cordovan version for Ralph Lauren called the the Marlow, and it has a slightly more unique shade of shell cordovan brown.

My own pair is Allen Edmonds’ Grayson. It’s quite similar to Alden’s, but it has a higher vamp, which is the part the shoe that covers the top part of your foot. I thought it looked slightly better this way, so I bought a pair in shell cordovan. I couldn’t be happier with the purchase and recommend them highly.

If you’d like more affordable options, consider Loake’s Lincoln and Meermin’s 101381. Both come in around $175, but Meermin has the added advantage of being able to do special orders. If you’d like to get a pair in shell cordovan or suede, or made from a different last or sole, they’d be happy to make you a pair for a small surcharge. I have a pair of their made-to-order shoes and couldn’t be more impressed with their value. To order, read this buyer’s guide and then go to Meermin’s website. My only comment on that guide is that you should ask Meermin for sizing advice; don’t just assume. 

Tassel loafers aren’t anything I’d call “an essential,” but they’re certainly very enjoyable to wear. If you work in an environment that lets you get away with more casual footwear, try wearing a pair of these with a wool sweater and corduroys, or maybe a checkered tweed and flannel wool trousers. Both will carry a great sense of American style that’s both casual and sophisticated. 

Casual Summer Footwear

Like most men of my generation, I rarely wear more “formal” clothes such as dark wool suits and black oxford shoes. Much of my wardrobe consists of more casual items, though I admit it leans towards the dressier side of things. That means lots of odd trousers and sport coats, casual button-up shirts, and shoes such as derbys, boots, and slip-ons. With the passing of Memorial Day and the unofficial arrival of summer, I thought I’d review some casual footwear options for the new season. Basically things that will work with what I think most men already have in their closet.

Generally speaking, I think men tend to look smarter in a pair of leather shoes than trainers. The one exception is white sneakers during the summer. For some ensembles, such as a pair of navy chinos and a colorful madras shirt, there may be nothing better. My favorites in this category include Superga, Chuck Taylors’ All Stars, and Vans’ Authentics, but there are many others. I covered a bunch of them last year in a post about plimsolls. In addition to those, you can consider the Common Projects and German Army Trainers that Jesse has talked about, as well as Svensson’s Classic Low Whites, Superga’s 1705s, and Superga’s decks. Svensson is a bit more refined looking, like Common Projects, but comes at a lower price point and even less branding. Men of Ilk is offering a 20% off discount code right now (GLCCW49), which puts the Svenssons at $180 for American customers. As for the Supergas, I bought a pair of the 1705s a few months ago and have been really enjoying them. The branding is less obvious and the design is basic enough to pair with most things.

For something slightly dressier, you can consider chukka boots. I know boots are a bit of an odd suggestion for summer footwear, but depending on your regional climate, I think they can work quite well. Alden’s unlined suede chukka, for example, is so soft and buttery that it wears very much like a slipper. The lack of leather lining inside makes the upper more malleable and breathable, much like a canvas shoe. My friend Stephen at The Simply Refined has said everything I could say about them. For something similar, you can consider Church’s Sahara and Allen Edmonds’ Amok. The brown version of the Amok is on clearance right now for $125.

If you prefer a bit more structure in your leather chukkas, you should check out Loake’s Kempton, Sahara, and Camden. Brooks Brothers also has a suede boot that gets discounted to $130 or so at the end of every season, and there’s of course Clark’s desert boots that everyone already knows about. If you have a bit more money to spend, I would also recommend A Suitable Wardrobe’s crepe sole chukka. I really like the shape of the toe box and think the crepe sole/ suede upper combination helps underscore the casualness of the shoes.

Finally, I’ll also suggest you get a pair of loafers this summer. Like with chukkas, these can be worn mostly year round, but feel especially nice for the warmer seasons. There are a good number of styles to consider, but for the purposes of this post, I’ll stick with the classic American penny loafer. Inspired by the Norwegian moccasin, the penny loafer was the sine non-qua for the post-war “Ivy Look,” and still looks quite sharp today. I recommend getting them from American manufacturers such as Alden, Allen Edmonds, Ralph Lauren, Brooks Brothers, Rancourt, and Oak Street Bootmakers. Bass also has some, though their quality is much lower these days. Outside of American companies, you may also want to look into Markowski, Herring, and Loake, as well as some of the models that Crockett & Jones offers.

Of course, there are dozens of good causal footwear styles, and some may be better suited for warm weather conditions than the ones above (e.g. espadrilles, white bucks, and spectators). However, for good, versatile basics that can work well for summer and transition into fall, I think you’d do well with white sneakers, suede chukkas, and leather penny loafers. 

streetetiquette:

Ali of A Noble Savage 

Let your smile be your umbrella, shielding you from those who would accuse you of wearing a tablecloth in your breast pocket.
(Seriously, outside of that absurd pocket parachute, this guy looks like a million.)

streetetiquette:

Ali of A Noble Savage 

Let your smile be your umbrella, shielding you from those who would accuse you of wearing a tablecloth in your breast pocket.

(Seriously, outside of that absurd pocket parachute, this guy looks like a million.)

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