Formal to Friday
Sixteen dress shoes, sorted by where you're going
Almost every dress shoe guide sorts by price, which tells you nothing, because a $200 black cap toe and a $200 suede loafer aren't competing for the same night out. The question that actually matters is what you're walking into.
So this page runs from the most formal shoe you can own down to the one that goes with jeans. Four bands, four picks each, and a note on every pair about how it looks and how long it lasts.
Every shoe here states how its sole is attached, in the brand's own words. That one line separates a shoe a cobbler can rebuild from one that gets thrown out when the sole wears through, and plenty of well known names never print it. If a brand wouldn't say, we couldn't either, so it isn't on the list.
The whole field
All sixteen on one ladder
Hover a dot to see which pair it is. The left end is a tuxedo and the right end is a pair of jeans, and almost everything you'll ever need sits in the middle.
Before you buy anything
The three ways a sole gets attached
There are only three ways the bottom of a dress shoe gets attached to the top, and which one you're holding decides how the shoe feels on day one and whether it's worth anything on day two thousand. It takes about ten seconds to check, and roughly half the brands out there won't tell you.
Goodyear welt
Built to be rebuilt
A strip of leather called the welt is stitched to the upper and the insole, then the outsole is stitched to that strip. Nothing goes through the inside of the shoe, so a cobbler can cut the outsole off and stitch a new one on without touching anything you paid for.
- Feels likeStiff for a few weeks, then it takes the shape of your foot and stays there.
- LifespanResole it as many times as the upper survives.
- Best forThe office shoe you wear most days.
Blake stitch
Slim, light, flexible
One row of stitching goes straight through the insole, the upper and the outsole from inside the shoe. There's no welt sticking out, so the sole sits flush with the upper and the whole shoe comes out narrower and lighter.
- Feels likeComfortable immediately. Almost no break-in.
- LifespanCan be resoled, but it needs a cobbler with a Blake machine.
- Best forDress shoes worn a few times a month, and loafers.
Handwelted
The old way, by hand
Same idea as a Goodyear welt, except a person stitches the welt to a ridge carved into the insole rather than a machine stitching it to a fabric rib. It takes hours longer and it's why handwelted shoes usually start where other shoes stop.
- Feels likeMoulds to your foot more closely than anything else.
- LifespanThe longest life of the three, comfortably.
- Best forThe pair you expect to still own in twenty years.
Occasion finder
Four questions, and it returns the band you should be shopping in plus the three pairs here that fit it best.
What's the occasion?
What are you wearing them with?
How often will you actually wear them?
What's the budget?
The picks
All sixteen, formal to casual
Filter by band, or just read straight through.
The most formal shoe you can own · Tuxedos and black-tie-optional
Black tie: Shiny, seamless and barely there
At the top of the ladder a shoe does as little as possible. No brogueing, no chunky sole, as few seams as the leather allows, and a finish that throws light back at the room. A wholecut is one piece of leather over the whole upper, which is the hardest way to make a shoe and the quietest one to look at.
You've got a black-tie thing on the calendar, or a wedding where you're the one standing at the front.
- GoodNothing on the shoe competes with the suit
- GoodThe one pair that makes a rented tux look bought
- GoodSlim enough to disappear under a trouser break
- TradeoffPatent and wholecut both show every scuff
- TradeoffToo dressy to wear to the office on a Tuesday
Suitsupply
Suitsupply Tuxedo Oxford in Patent Leather
High-gloss patent on a sleek pointed last, which is the exact look black tie asks for and a look almost nothing else pulls off. Blake stitching keeps the sole edge tight to the upper so the whole shoe stays slim, and slim is the entire brief here. You'll wear it five times a decade and it'll be right every time.
Meermin
Meermin Linea Maestro 102635 Wholecut Oxford
A wholecut is one piece of leather wrapped over the last with a single seam at the heel, so there's nothing to catch your eye and nowhere to hide a flaw. Meermin's Linea Maestro line is their handwelted tier, which is the old way of doing it and normally sits at triple this price.
Beckett Simonon
Beckett Simonon Valencia Wholecuts
The same one-piece upper as the shoes above at well under half the money, in Italian calfskin with a clean rounded toe. Beckett Simonon gets there by making shoes only after they're ordered, so nothing sits in a warehouse and nothing gets marked down. You pay for the shoe and not the inventory.
Grenson
Grenson Shoe No.2 Oxford in Black Calf
Grenson has been making shoes in Northamptonshire since 1866 and the No.2 is the plain black oxford they'd point at if you asked what they do. Narrow waist, a toe with actual shape to it, and a leather sole that gets thinner toward the arch. It's the most expensive shoe here and it looks like it from across a room.
The serious occasions · Weddings, funerals, first days
Weddings and interviews: The cap toe, and why it never loses
A black cap toe oxford is the least interesting shoe in any room and that's exactly the job. Closed lacing, a line across the toe, nothing else going on. You can wear one to a wedding in the morning and a funeral in the afternoon and nobody will think about your feet either time, which is the whole point.
You want one pair you can put on without thinking whenever the invitation says anything more than smart casual.
- GoodRight for every formal event that isn't black tie
- GoodReads correct with navy, charcoal and black alike
- GoodThe safest shoe to own if you only own one
- TradeoffBlack cap toes want a suit, not chinos
- TradeoffThey need polishing, and it shows fast when you skip it
Johnston & Murphy
Johnston & Murphy Melton Cap Toe
The default American cap toe, and the one that solves the problem nobody else on this page solves: it comes in five widths and sizes up to 16. If your foot has never really fit a dress shoe, start here. Welted, so the leather settles into your foot's shape over the first month instead of fighting it.
Carmina
Carmina 80201 Cap Toe Oxford in Black Boxcalf
Carmina has been making shoes on the same Spanish island for five generations, and this is the plainest thing they sell: a black cap toe on their Rain last, welted, leather lined, leather soled. It's the shoe you buy when you've decided to only ever buy one black oxford.
Charles Tyrwhitt
Charles Tyrwhitt High-Shine Leather Luxury Oxford
Tyrwhitt does the hard part for you. This one arrives with the toe and heel burnished to a proper shine, which is a job that takes most people an evening and a lot of swearing. Blake stitching keeps it light and close-cut, so it reads dressier than the price bracket usually manages.
Allen Edmonds
Allen Edmonds Park Avenue Cap-toe Oxford
The Park Avenue is the shoe American offices have been wearing for decades, and the thing that keeps it here is what happens in year six. Allen Edmonds will take the pair back, strip it to the upper and rebuild it on a new sole. That turns an expensive shoe into a cheap one if you keep it long enough.
Five days a week · Monday through Friday
The office: Brown, burgundy, and built to be rebuilt
Down here the shoe gets a little friendlier. Brown or burgundy instead of black, a bit of brogueing or a strap instead of a plain toe, and usually more leather underfoot because it's going to get walked on. This is the band where construction matters most, because these are the shoes that rack up miles.
You're dressing for work most days and you'd rather buy one good pair now than three cheap ones over the same stretch.
- GoodBrown and burgundy go with more of your closet than black does
- GoodTakes scuffs and looks better for them
- GoodWelted pairs here can be resoled instead of replaced
- TradeoffBrown is wrong at a funeral and borderline at a black-tie wedding
- TradeoffA daily shoe wants a second pair so it can rest
Johnston & Murphy
Johnston & Murphy Ashton Plain Toe
Brown full-grain, no cap, no brogueing, nothing to fuss over. Full-grain leather is the top layer of the hide with nothing sanded off it, so it scuffs into a patina instead of peeling. This is a shoe you stop thinking about after a week, which for a work shoe is the highest compliment there is.
Florsheim
Florsheim Kenmoor Wingtip Oxford in Burgundy
A longwing, meaning the brogued wing runs all the way back to the heel instead of stopping at the toe, on open lacing and a double leather sole. The burgundy goes with navy and grey better than black ever does, and it's the least expensive way on this page into a shoe a cobbler can rebuild.
Beckett Simonon
Beckett Simonon Hoyt Monkstraps
Two straps and a buckle instead of laces, which somehow reads as more considered than an oxford without reading as showy. It sits neatly between a formal shoe and a loafer, and it's the pick that gives an ordinary grey suit something to talk about at the floor.
Grenson
Grenson Camden Derby in Black Leather
Open lacing, which means the two flaps sit on top of the vamp rather than under it. That's a derby, and it's both slightly less formal than an oxford and a lot more forgiving if you have a high instep. Grenson builds this one heavy enough to take a daily commute.
The loafers · Dinner, drinks, Friday
Dressy with jeans: No laces, no fuss
The bottom of the ladder isn't the bottom of the quality. These are proper leather shoes with proper soles that happen to look right with dark denim. A loafer is the shoe that lets you keep the jeans and still look like you thought about it, and it's the pair most guys end up wearing more than anything else here.
You want a real shoe for the nights and weekends where a sneaker is too little and an oxford is too much.
- GoodWorks with jeans, chinos and an unstructured suit
- GoodOn and off without bending down
- GoodSuede softens the whole outfit without dressing it down
- TradeoffA loafer is too casual for a formal wedding
- TradeoffSuede and heavy rain are a bad pairing
Meermin
Meermin 514511 Unlined Penny Loafer in Atacama Suede
Unlined, so there's no second layer of leather between your foot and the suede and the shoe gives immediately instead of asking for a break-in fortnight. Meermin built a new last for this range with a tighter heel, which is the fix for the one thing loafers usually get wrong.
Suitsupply
Suitsupply Dark Brown Penny Loafer in Suede
Dark brown suede with a fine, even nap and a slim blake-stitched sole, which is the combination that lets a loafer go under tailoring without looking like you gave up halfway. Wear it with jeans on Saturday and an unstructured navy suit on Tuesday and it's the correct shoe both times.
Allen Edmonds
Allen Edmonds Randolph 2.0 Penny Loafer
A single leather sole keeps this one low and sleek instead of chunky, which is what separates a dress loafer from a casual one. Same deal as the Park Avenue further up the page: when the sole finally goes, Allen Edmonds will rebuild it rather than you replacing it.
Todd Snyder
Todd Snyder X Alden Venetian Leather Loafer
A venetian loafer has no penny strap and no tassel, just a clean sweep of leather across the vamp, which makes it the quietest slip-on there is. Alden builds it in Massachusetts on the Aberdeen last, and Todd Snyder gets an exclusive run so you don't have to chase a stockist.
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