Dress code decides which of these pairs you wear: a black oxford for a wedding, interview or funeral, a black derby for an ordinary workday, and brown leather sneakers, white minimalist sneakers or black canvas sneakers for a relaxed Saturday.
Cedar shoe trees, a horsehair brush and monthly polish keep the leather ones going for years.
1. Black Oxford Shoes
A black oxford is the most formal shoe a man can own, and the closed lacing is what makes it so. The eyelets are stitched under the vamp, so the shoe sits sleek against the foot.
Wear it with a suit in grey, navy or charcoal, and match your belt to it.
Keep the leather polished. A scuffed black oxford looks worse than no effort at all.
Jeans and chunky knits are a mismatch. For weddings, interviews and funerals, this is the pair I’d buy first.
2. Chelsea Boots
Slip-on ankle boots with an elastic side panel, Chelsea boots are the easiest cool-weather shoe to get out the door in. With no laces to deal with, a Chelsea is the fastest boot to pull on and go.
Dark brown leather works with blue jeans, chinos and wool trousers alike. I’d choose a slim, plain toe over anything chunky, since the clean line is the whole appeal.
Let the trouser hem sit over the top of the boot or just brush it. Cuffed jeans stacked on the shaft look cluttered.
3. Suede Loafers
Soft, napped and a little casual, suede loafers suit a man who wants something dressier than sneakers without the stiffness of leather dress shoes. Brown is the safest first color for suede loafers, with black a distant second.
Pair them with chinos, linen trousers or dark denim, and go sockless or wear low-cut socks.
Suede dislikes rain and stains, so keep a suede brush on hand and skip them on wet days. That is the price of the texture, and I think it’s worth paying.
4. Chukka Boots
Chukkas stop at the ankle and carry a short row of eyelets, which makes them the boot I reach for when a Chelsea feels too sleek and a work boot too rugged.
Brown suede is the friendliest version of a chukka.
Wear them with jeans, chinos or a soft, unstructured jacket. Keep the trousers slim to mid-width so the boot isn’t swallowed.
Suede scuffs and spots easily, so a protective spray is a sensible first purchase. Smart casual is their territory; a suit is not.
5. Penny Loafers
Penny loafers are slip-ons with a saddle strap across the vamp, and they run easier than any lace-up shoe. Burgundy leather gives you more character than plain black or brown while still matching most outfits.
Dark grey or navy trousers, chinos, even cropped jeans all work. Whether to wear socks is a choice: crisp white ones read preppy, while no-show socks keep things quiet.
Pick a snug fit at the heel, because loafers loosen with wear. For offices that skip the tie, they fit well.
6. Monk Strap Shoes
Buckles replace laces on a monk strap, and that single change makes the shoe feel distinctive while staying dressy. A double strap is the bolder version of the monk strap; a single strap is quieter.}
Brown leather pairs well with navy trousers, grey flannel and tailored chinos. I like them best under a suit that’s a little less stiff than the black oxford crowd would wear.
Fasten the buckles snugly but without squeezing the instep. If you want a dress shoe people notice for the right reasons, start here.
7. Brown Leather Sneakers
Brown leather low-tops with a white sole sit right between a gym shoe and a dress shoe, and that’s why they earn a spot.
Leather reads neater than canvas, so the same pair works with jeans on a Saturday and chinos on a casual Friday.
Cuffed dark denim shows off the shoe and keeps the line clean. A single narrow cuff is enough.
Wipe them down now and then and keep the leather conditioned.
Brown leather sneakers are the pair I’d wear to a relaxed office, since the smooth leather and muted color read closer to a casual derby than to a gym shoe.
8. Brown Wingtip Brogues
Wingtip brogues carry the decorative perforations and the pointed toe cap that wraps back toward the laces, and in brown leather they are the most useful dressy shoe after a black oxford.
Closed lacing keeps them formal enough for a suit.
Wear them with navy or grey trousers, or with chinos and a sport coat when you want a little more texture. I’d pick a mid-brown over a very light tan, which is harder to match.
Brogue detailing is busy, so keep everything else you wear quiet. Match your belt to the leather.
9. Black Derby Shoes
Derbies have open lacing, where the quarters sit on top of the vamp, and that makes a black derby a touch less formal than a black oxford. It’s the easier shoe to wear on an ordinary workday.
Grey dress trousers and a blue blazer are a dependable partner, and charcoal or navy suits work as well. Keep the leather polished and match the belt.
Open lacing also suits a wider foot, since the shoe adjusts more easily across the instep. If you own the oxford already, this is the pair for days when it feels like too much.
10. White Minimalist Sneakers
White leather sneakers with a plain upper and a single logo are the cleanest casual shoe I know. A brown sole, like the one on these Pumas, warms the white and hides some wear.
Wear them with chinos, jeans or shorts, and keep the other pieces simple: a solid tee, an overshirt, nothing loud. Low-cut socks work best.
White shows dirt, and that is the real cost. Wipe them after each wear and don’t let marks set.
11. Black Canvas Sneakers
Black canvas low-tops with white laces are the cheapest shoe on this list and the easiest to throw on. Light and flat, they suit warm days and a relaxed weekend.
Blue jeans and a white tee make the simplest outfit, and I’d keep it that way. Black hides dirt better than white canvas does.
Canvas offers little support and no polish, so skip them for work, dates at nicer restaurants or anything dressy. For running errands, they do the job.
Shoe Care Tips
Rotate your pairs. Leather needs a day or so to dry out between wears, and a shoe worn daily breaks down faster than two worn on alternate days.
Put cedar shoe trees in as soon as you take the shoes off. Cedar shoe trees keep the leather from creasing and curling, and the wood draws out the moisture your feet leave behind overnight.
Brush off dust after wearing, and use a leather cleaner when the surface is dirty.
For a shine, I reach for a horsehair brush; its bristles lift dust from the welt and buff polish to a soft glow. Condition with a good shoe cream so the leather doesn’t crack, and polish leather monthly.
Use a product made for suede, and keep it away from leather creams and polish.
Once a sole wears down, replace it. A resoled pair costs far less than a new one, and good shoes can last for years if you keep up with this routine.
Styling for Occasions
Start with the dress code, then pick the shoe.
A suit for a wedding or a formal evening calls for a polished leather dress shoe with a sleek profile, and a sharp, shiny pair is still the right call for date night too.
Black-tie leaves almost no room: a black oxford is what I would wear.
Cap toes or plain toes will do the job. Choose premium leather and a slim shape over a chunky one.
Dress shoes also don’t have to stay in formal settings.
Keep the rest of the outfit quiet, and a dressier pair can make a casual look feel sharper instead of overdressed. Try them with dark denim and a plain knit.
Sneakers and loafers belong to casual outings.
If you’re unsure how formal an event will be, go one step dressier than you think you need. It’s easier to look slightly sharp than slightly careless.
When you’re suiting up for date night, a wedding, or any other type of formal occasion, a slick and shiny pair of dress shoes is still the way to go. But don’t limit this formal footwear to buttoned-up occasions.
— GQ
Frequently Asked Questions
What are essential shoes for men?
A black oxford, brown wingtip brogues or a black derby, a pair of loafers, Chelsea boots and a clean pair of sneakers cover most situations.
The oxford handles weddings, interviews and funerals, while the boots, loafers and sneakers take care of everything casual. Other pages that cover this give a similar mix: oxfords, derbies, loafers, boots and sneakers.
What shoes are cool for guys right now?
White sneakers and Chelsea boots are the 2 styles pages covering current trends point to most.
Either one fits into most closets without effort: the sneakers handle chinos, jeans and shorts, and a slim plain-toe Chelsea in dark brown leather looks right with denim, chinos or wool trousers.
Loafers are also named as a favorite among fashion-conscious guys.
