Ever since I first got interested in menswear by reading magazines like GQ or Esquire, then eventually joining online communities to learn about clothing, I’ve noticed magazine stylists, celebrity stylists, personal shoppers and more were putting guys in suits with sneakers on their feet.Â
Doing that attempts to solve for 2 issues: 1—Comfort for the guy’s feet, as it takes a bit of time and energy to get a good fit for leather-bottom dress shoes that are comfortable to wear all day; and 2—Casualizing tailored clothing, as suits, sportcoats and tailoring in general is less and less ubiquitous in daily life, and therefore people are always looking for ways to freshen it up.
But the problem is that tailored clothing is like a great white shark: It’s a fully formed mode of dressing, with each piece having a well established form, and you’re best coloring within the lines. So a business suit with a pair of white sneakers usually looks bad.
Then something strange happened: Shoe companies started creating dress-shoe-sneaker-hybrids, by adding sneaker soles to the upper of what otherwise looks like a normal dress shoe. I see these all the time on guys, which is heartening since it tells me guys have at least a little bit of sense not to attempt to dress up sneakers. And I totally understand the impulse to wear them, as the sneaker sole is more forgiving in comfort.
But again, my problem with them is that they’re ugly. I think the intent from the shoe companies making these is to lean into the sneaker-sole, rather than downplay it, so they make them white and sometimes put colors on them. Allen Edmonds’ most iconic dress shoe with a white sneaker sole, for example, or their Randolph penny loafer. It hurts my heart to see those shoes. Meanwhile, their latest actual sneaker has tastefully color-matched soles to the dark brown suede upper. Down is up. Left is right.
So I’m telling you: just stop. Don’t wear hybrid dress-sneakers. Wear a leather sneaker by all means (honestly that brown suede AE Barnes is nice if you like that style of sneaker). But don’t wear a dress shoe with a sneaker sole.
Which begs the question: what should you wear instead? I’m glad you asked, here are some suggestions.
First, a quick note on leather: I go for suede for most shoes. It wears easier for both dressed-up and dressed-down-but-still-kinda-dressy fits. I write about this in my eBook which you can buy here. But the majority of my suggestions below are going to be suede.
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“Traveler” Style Belgian Loafers
Belgian loafers have this whole New York cult following going back a long time. Originally they were only made with thin leather soles, sort of like slippers, which would wear through quickly, but stylish dudes like David Coggins would take those well-worn pairs and wear them to the beach. I was won over a couple years ago after realizing many of the photos I’d saved of stylish guys over the years were wearing Belgians in those photos. The appeal of Belgians is their low vamp (the top part of the loafer) and the nice shape it has, while being an otherwise lightweight and simple shoe. They can dress up with tailoring, including suits (just not the most formal business suits; here’s some more help on identifying what that looks like), but can also look great with jeans or chinos.
In the last decade or so the Belgian shoe designers created a version with a rubber sole. And as they’ve grown in popularity more makers are creating them so you’re not only having to pay $600 for the originals.
I’ve tried a few styles, and by far the most comfortable are these two:
Crown North Hampton’s Artizan loafer. The sole is significantly more subtle, as it’s underset a bit, almost more like a slipper. I wore these walking all afternoon on the cobblestones of Florence in June and was comfortable the whole time. Read my short write-up about Crown North Hampton here.
Myrqvist’s Angby Suede Belgian loafer. These have the more typical black rubber sole other Belgian shoe makers use. Out of the box the collar of these (the part that goes around your achilles heel) was tight, digging into my achilles; I put wooden shoe trees in them so the back of the shoe tree pushed against the collar, and it stretched it out. I can now wear them comfortably all day. Less comfortable than the Crown North Hamptons by 10% but not painful by the end of the day.
Other options are the originals, simply called Belgian Shoes; Baudoin & Lange’s; Skolyx’s Yanko Belgians (these are not a great fit for me).
Desert Boots
Annoying people will whine about desert boots being basic, but honestly if I see a guy show up in desert boots and chinos, I can’t help but smile in approval. Desert boots are like Jeeps—honest menswear staples that helped win the war against the Nazis (so are chinos for that matter), and in my mind you can’t go wrong. The crepe sole makes them more comfortable than hard leather-bottom shoes.
Desert boots are not good with a fully tailored fit—but with chinos and denim, perfect. Maybe I’d wear desert boots with a pair of somewhat full-fitting tailored dress trousers in a fabric like cotton or linen (ironed with a crease) and a shirt with rolled-up sleeves. In other words, lean into that military heritage. Since desert boots are a rounded toe shape, they work best a bit more casually.
My favorite two makers for desert boots are these:
Crown North Hampton’s Woodford desert boot. Read more about it here, but these are constructed like the desert boots your grandfather wore in WWII. I added leather tongue pads to the tongues to make the lacing a bit more comfortable.
Astorflex Brownflex desert boot. They have a few styles but the Brownflex is the most classic desert boot looking one of them (with a low toe profile, specifically). These are nice because they have a removable insole, meaning you can put in one from, say, Superfeet, to add more heel or arch support without bulking up the shoe.
Other makers are: Of course Clark’s Originals desert boot, which was kind of the OG but which has offshored manufacture and is less good than the above two (though it has a price to match), and I also don’t like the colors of suede they make as much, though the cola suede linked I do like; Drake’s Clifford desert boot (which are made by Astorflex but on a special last that’s better than Astorflex’s own).
Canoe Moccasins
The moccasin style of shoe is most popularly found on boat shoes. Those have a much more decidedly preppy connotation, but the one-eyelet version, called some variation of canoe moc or camp moc, is better IMO. They have the same comfort and casual vibes as a boat shoe but without the prep baggage. These wear similarly to a desert boot in formality: wear it with chinos or lower in formality. I’ve worn them with chinos + a blazer successfully in the past.
My favorite canoe moccasin maker:
Sid Mashburn camp mocs. Made in Portugal, so a bit cheaper than the MiUSA versions, but a great choice.
Oak Street bootmakers. These are made in the USA. The chromexcel color is the best. They’re well made and comfortable and will last a long time.
Tyrolean Shoes and/or Wallabees
These are honestly kind of ugly but I’ve come to love them, and they have more of a point of view than plain leather sneakers TBH. They’re chunky and have the apron toe construction. The traditional style is a rounded toe with waffle-stomper rubber soles. Clark’s makes a similar shoe called the Wallabee which is on an uber comfortable crepe sole, and the toe shape is… foot-shaped (?). It’s not round, it follows the contour of your foot. Again I wouldn’t wear these with suits, but it has been done by guys with eccentric style (Wes Anderson specifically), so if you want to do it go for it just stick with casual suits like in corduroy, cotton twill or similar.
Makers I’d recommend:
Clark’s Wallabees. I own these in the low-top version in cola suede, and they’re kind of my go-to travel shoe now on account of how comfortable they are.
Padmore & Barnes. This is the Irish factory that originally made Clark’s before they were offshored. So kind of the real OG. Better color selections than Clark’s TBH. Better quality, too, and the toe shape is a little better too.
Skolyx’s Yanko Tyrolean. I just got these and they’re comfortable out of the box.
August 1963, my first day in Hales Franciscan High School (Chicago). Dress code – a shirt and tie, and crepe soled shoes (they made less noise in the halls, and didn’t scuff the floors). 2025, I still wear crepe soled shoes (Clarks desert boots and Wallabees). Two years ago, I bought my first pair of Sperry Top Siders. I only wear sneakers when I’m out cutting the grass.
I’ve found when the Sperry’s wear out, they work well for cutting the grass. Growing up, my dad had a pair of leather desert boots that became his stepping-outside shoes right by the door, to get the mail or step outside for a moment, and they just would. not. die. My brother and I marveled at how the entire shape of those had been destroyed and flattened, yet for years they persisted. I don’t think they make them that well anymore (I recently got a pair of their Gold Cup and indeed they’re much nicer than the normal ones, so perhaps these will last that long).
Just a heads up regarding the camp mocs: Chromexcel isn’t a color, it’s a type of leather tannage.
I have oak street’s camp moc in their natural Chromexcel roughout (suede) and they’re supremely comfortable, and pair nicely with fatigues and denim and shorts, though the dark brown and natural colored smooth leather versions would pair nicely with casual chinos as well.