The Best Men's Dress Shoes: Oxfords, Derbies, Monks and How to Wear Them

The men's dress shoes to buy first are black calf oxfords with a plain or cap toe on a slim sole. They go with every navy, charcoal and gray suit and with almost every invitation short of black tie. Add a dark brown pair for gray and earth-toned tailoring, a derby or monk strap for long days on your feet, and patent or velvet for the evening. Below we take the styles in order of formality, from John Lobb and Berluti to Ferragamo and Christian Louboutin, then the details that separate a good pair from an expensive one: construction, leather, sizing on real listings, color by suit and care.

Men's dress shoes, from most formal to least

Two things set a dress shoe's rank: how it laces and how much decoration it carries. An oxford has closed lacing, its eyelet panels stitched beneath the front of the shoe, so the lacing lies flat. A derby's panels sit on top and open outward, which reads a notch less formal. After that, every punched hole and buckle moves a shoe a step further from black tie.

Oxford shoes for men: start with a black cap-toe

If you buy one dress shoe, make it this. The cap-toe's straight seam gives the shoe shape without ornament, and in black calf it is right with navy, charcoal and gray suits at work, at weddings, at funerals and at dinners short of black tie. In our experience the toe decides how long you will wear it: a round or almond toe looks as good in ten years as now, while an exaggerated point dates fast.

Zegna's Torino is hand-buffed calf with Blake construction, on a leather sole with rubber inserts at toe and heel, and its listing says it fits true to size. John Lobb's Bristol, made in the UK by its listing, adds a line of perforations on a rubber outsole, the sensible choice for a wet commute. Christian Louboutin's Seriox is semi-matte calf over the house's red sole; Ferragamo's Boston edges its cap with brogue detailing that reads plain from a few feet away. Tom Ford's Elkan has a squared toe and a high shine.

• Navy worsted suit, white shirt, burgundy silk tie, black cap-toes and a black belt.
• Charcoal flannel suit, pale blue shirt, navy knitted tie and black cap-toes.
• Mid-gray suit, white shirt, black grenadine tie and black cap-toes, for a daytime wedding.

Whole-cut and plain-toe oxfords

A whole-cut is made from one piece of leather with a single seam at the back. With nothing to interrupt the surface it is the sleekest day shoe and the most exacting, because every crease shows, so buy it in the best leather you can. John Lobb's listing describes its Marldon as cut from a single piece and Goodyear-welted.

Two companies trade as John Lobb, and they are easy to confuse. The one whose ready-to-wear shoes are sold here belongs to Hermès. Bootmaker John Lobb opened in London in 1866 and in Paris around 1900; in 1976 the Hermès group bought the French business, which began making ready-to-wear collections in 1982 and still makes some of its shoes in Northampton, according to the Comité Colbert. The bespoke workshop at 9 St James's Street in London is a separate company: its own history records that only the French arm was sold in 1976, and the Lobb family still runs it.

Berluti cuts its Blake whole-cut (Blake is the model's name, not its construction) from Venezia leather, which its listing says is meant to show the patina the hide gains over time, and sets it on rubber soles; the house's plainer black oxford ships with wooden shoe trees. Manolo Blahnik's Snowdon is a whole-cut in glossed leather. Plain-toe oxfords, such as Canali's and Ferragamo's Angiolo, keep the closed lacing without a cap; Brunello Cucinelli's glossy pair adds a split rubber sole for a day that may turn wet.

A black whole-cut is also the one day shoe that can follow you into black tie, since Debrett's, the British etiquette authority, accepts black highly polished lace-ups alongside patent. In our experience it needs a real shine to pass at night: build the polish on toe and heel.

• Black whole-cuts, a charcoal or midnight suit, white shirt and a silver-gray tie, for an evening wedding.
• Berluti's brown whole-cut with a mid-gray flannel suit, a white shirt and an olive knitted tie.

Brogues and wingtips: how much decoration a suit can take

The English shoemaker John White traces broguing to Irish and Scottish field shoes, whose perforations let water drain out on boggy ground, and the name to the Irish word for shoe, bróg. In town the holes became decoration, and the rule since has been simple: the more punching, the more casual the shoe.

A quarter brogue punches only the seam of the toe cap and usually has no medallion. A semi-brogue adds a medallion, a rosette of holes, at the toe. A full brogue, or wingtip, has a W-shaped cap whose wings sweep down both sides; a longwing carries them to the heel, as on Thom Browne's Classic Longwing. Leather moves the reading as much as punching: a black calf semi-brogue sits under a worsted business suit, while a suede wingtip belongs with flannel and tweed.

Ferragamo's Sebastiano is a semi-brogue, Blake-stitched for what its listing calls a slim, flexible finish; the house's Albert keeps a plain cap and punches the quarters instead. John Lobb's Hartland is a semi-brogue in navy calf, a quiet partner for a gray suit. Kiton's Caravaggio is cut almost like a whole-cut, punched only along the topline and at the toe, and Versace's is a full brogue in high-shine black. Kiton's and Tod's suede wingtips lace open, derby-style.

• Black semi-brogues, a charcoal worsted suit, white shirt and a burgundy tie.
• Dark brown suede wingtips, a mid-gray flannel suit, white shirt and an olive knitted tie.
• Navy semi-brogues with a light gray suit and an open-collared white shirt.
• Black longwings, charcoal flannel trousers, a gray tweed jacket and a white button-down.

Derby shoes: open lacing, more room

A derby suits a high instep, a heavier sock or a foot that swells by evening, because its open facings can be let out without the shoe gaping. In plain black calf on a slim sole it is entirely correct with a business suit. Our stylists' pick for a man who stands all day is a black derby on a thin rubber sole: it grips a wet lobby floor and stays quiet in a meeting room.

Saint Laurent's Stanton is glazed calf on a leather sole with a one-inch heel, by its listing. Prada's brushed-calf derby and Gianvito Rossi's polished William Smart sit on rubber; Berluti's Alessio, in Venezia leather and lightly padded along the sides, has the thickest rubber sole here and is the pair we would keep for odd trousers rather than a sharp suit. Manolo Blahnik's Newbury has tonal topstitching around an apron toe, a country seam that still looks neat with tailoring.

• Black derbies, a navy suit, white shirt and a navy tie.
• Black rubber-soled derbies, charcoal trousers, a gray sport coat and a white shirt, for a day of meetings in the rain.

Monk straps, single and double

A monk replaces the laces with a strap and buckle, the one dress shoe with jewelry built in. It belongs with a suit and never with a tuxedo: Debrett's asks for lace-ups at black tie, which leaves the buckle out. A single monk is plainer and, to our eye, a little dressier than a double. Fasten both buckles of a double monk, and ask your tailor for little or no break, because the buckles sit where a long hem catches.

Jimmy Choo's Finnion is brush-off leather with gunmetal-tone buckles on a leather sole. Ferragamo's double monk uses the house's Tramezza construction, which its listing describes as a soft leather layer between sole and insole. Versace's Primo adds brogue punching and a Greca-engraved buckle; Ferragamo's Sullivan is a single monk in hand-buffed burgundy calf.

• Black double monks, a charcoal chalk-stripe suit, white shirt and a silver-gray tie.
• Burgundy single monks, a mid-gray flannel suit, pale blue shirt and a navy knitted tie.
• Brown suede monks, olive wool trousers, a cream rollneck and a beige cashmere jacket.

Dress loafers that can stand in for a lace-up

A loafer can go with a suit when it is built like a dress shoe: black calf, a slim sole, a low heel and little hardware. That leaves out driving shoes, lug soles and large logos. Brioni's penny loafer sits on a leather sole and Zegna's plain penny loafer is smooth calf, by their listings; Prada's Venetian is brushed leather with a moc toe on rubber; Alexander McQueen's Wishbone adds one gold-finish buckle. Outside patent, keep loafers away from black tie. Our guide to the best loafers for men covers penny, horsebit and tassel styles in depth, and men's loafers has the full range.

• Black calf penny loafers, a charcoal suit and a white shirt with no tie.
• Black loafers, a mid-gray flannel suit and a black merino rollneck.

Dress boots for a suit in winter

In snow or slush a boot can stand in for an oxford if it keeps the oxford's lines: a slim shaft, a dress sole and a toe no heavier than your shoes'. Gianvito Rossi's Alain Torino sits on a leather sole; Givenchy's Tux, in brushed bull leather, has a flat 5 mm heel; Tom Ford's burnished Chelsea has a pointed toe on a stacked heel of just under 1.4 inches; Manolo Blahnik's Sempione, in polished leather, uses ribbed-knit side panels. For wet streets, Tod's and Prada's tapered saffiano pair sit on rubber, as does John Lobb's Regi, from its Officer line, which closes with a discreet side zip instead of elastic.

Check the side view in a mirror, in the trousers you will wear: the hem should cover the elastic gusset completely, and a trouser cut with no break may need lengthening to do it. For jodhpur boots, see our men's fall boots guide; for snow and salt, our guide to men's winter boots; for more pairs, men's Chelsea boots.

• Black Chelsea boots, a charcoal flannel suit, white shirt, black knitted tie and a charcoal overcoat.

Men's formal shoes for black tie: patent and velvet

Holiday parties between Thanksgiving, on Thursday, November 26, and New Year's Eve are when an evening shoe earns its place. For black tie, Debrett's asks for “black highly polished or patent lace-up shoes and black silk socks.” A monk strap is out, and in our stylists' view so are broguing, a thick sole and a wide square toe, which fight the plainness of a dinner suit.

If you own one evening shoe, make it a plain patent oxford, with a black whole-cut polished hard as the fallback. A patent pump or velvet slipper is the laceless alternative, which we keep for a party you host or a creative black-tie invitation. Christian Louboutin's Greggo Galvin is patent with a grosgrain-edged cap; Brioni's high-shine slip-on, edged around the opening, is the nearest thing here to a pump; Saint Laurent's laceless Milton has a mirror shine; and Louboutin's Chambeliss is a lace-up derby in black velvet. Prada's patent lace-up laces open, like a derby, so we would keep it for black tie optional, and Dolce & Gabbana's high-shine Chelsea boot is our pick for a creative black-tie party on a snowy night. In our experience patent needs only a soft, damp cloth; wax polish dulls it.

Our guide to men's tuxedos covers the rest of the black-tie outfit, our men's holiday party outfits take each December dress code in turn, and how to dress for black-tie events covers the evening for both of you.

• Patent oxfords, a black peak-lapel tuxedo, a white piqué-bib shirt, a black silk bow tie and over-the-calf black silk socks.
• Black velvet derbies or slippers, a midnight dinner jacket, black tuxedo trousers and a white pleated shirt, for a party you host.

Dress shoes for suits: which color goes with which suit

Vêtir's stylists keep two pairings out of every outfit: brown, tan or cognac shoes with a navy, blue or black suit, and black shoes with a brown, camel or tan suit. So navy goes with black, or with a true burgundy, and a man whose suits are mostly navy needs black shoes first. It is how our stylists dress rather than a law of menswear, and it keeps a small shoe wardrobe simple.

Choose burgundy from the photograph, because some leathers sold as oxblood come out close to chocolate, and match the belt to the shoes in color and finish. If your suits are already in your Vêtir closet, ask our AI stylist which pair each one needs, and see men's suits for the tailoring.

The edit below is for the gray side of the wardrobe: Ferragamo suede oxfords, Zegna's Torino in hand-buffed dark brown, Kiton's open-laced cognac pair, John Lobb's tonal-brown Marldon, and derbies from Gianvito Rossi, Manolo Blahnik and Brunello Cucinelli.

How a good pair is made: construction and leather

Goodyear welt, Blake and cemented

Much of a dress shoe's price goes into how the sole is attached, the detail a listing is least likely to mention. The three methods, as the Northamptonshire shoemaker Loake defines them in its glossary of construction and leather terms, with our view of each in wear:

• Goodyear welt. A leather strip, the welt, is stitched to the upper and insole, and the outsole is stitched to the welt, so the outer seam runs around the edge of the sole rather than through the part under your foot; the space between insole and outsole is filled, often with cork. In our experience it is the sturdiest of the three and the easiest to resole, at the cost of a slightly wider edge.
• Blake. The outsole is stitched straight through to the insole. The shoe is slimmer and more flexible; the trade-off, to our minds, is a seam you can sometimes feel underfoot and a shorter path for water.
• Cemented. The sole is bonded to the upper with adhesive instead of stitching. It makes a light shoe, but not one we would buy expecting a second sole.

In this guide, John Lobb states Goodyear welting for the Marldon; Zegna's Torino and Ferragamo's Boston and Sebastiano state Blake; and Ferragamo's Tramezza pairs, by their listings, layer soft leather between sole and insole in about 160 steps. When a listing is silent, we would not assume.

Calf, corrected grain and suede

Loake's glossary also draws the leather line that matters. Calf or full grain has not been sanded or corrected, breathes, and develops a patina as it ages. Polished or corrected-grain leather has its surface corrected and a top coat added for shine; it resists water and staining better and starts stiffer, but it will not develop the same patina. In our experience the difference shows within two seasons: calf creases softly and deepens in tone, while a coated finish keeps its gloss and creases in sharper lines. Suede is a day leather; on a rubber sole, with a protective spray, it copes with a damp afternoon.

Sizing and fit: UK, US and European numbers, and width

The number on the box changes with the house, so read each listing's labels before comparing. In this guide:

• John Lobb's Bristol and Jamie mark a UK 7 as a US 8 in a D width, and Prada's derby and Venetian loafer use the same UK-to-US labels.
• Tod's marks a UK 7 as a US 8.5 on its suede wingtip, so the gap is not fixed from house to house.
• Christian Louboutin's Seriox, Givenchy's Tux Chelsea and Tom Ford's burnished Chelsea mark a European 41 as a US 8.
• Ferragamo adds a width letter to its US sizes, EE on the Boston and Sebastiano and E on the Tramezza double monk, on its own scale: the chart printed on its listings calls D narrow, E standard and EE wide, where American sizing usually treats D as standard.

Read the fit note too: Zegna says its Torino fits true to size, Christian Louboutin's calf Greggo is listed as small to size, and Ferragamo suggests a size down in its Funes loafer. English makers count width differently again: Loake, for instance, defines E as narrow, F as regular, G as wide and H as extra wide, roughly a quarter-inch of girth apart, and notes there is no absolute standard. If you need a wide shoe, buy from a house that states one.

Our stylists' checks in the fitting room, wearing your usual dress socks:

• Lace an oxford firmly. You should see a slim, even channel between the two quarters; quarters that touch mean too much room over the instep, and a gap that widens toward the top means too little.
• Rise onto your toes. The shoe should crease across the widest part of your foot, where it bends, not in front of it.
• Walk for a few minutes on a hard floor before deciding; a shop carpet hides heel slip.

Care, shoe trees and resoling

Our stylists' routine: a shoe horn every time, so the heel counter keeps its shape. Put cedar shoe trees in as soon as the shoes come off, while the leather is still warm and damp. Rest a pair for a day between wears so it dries out properly, and dry a rain-soaked pair slowly at room temperature, never on a radiator. Give smooth calf a thin coat of wax polish every few wears, and wear new leather soles on dry days first. In our experience, two pairs of black shoes worn on alternate days each outlast a single pair worn every day.

Resole a welted pair while the old sole still has some thickness; once wear reaches the welt, the repair grows. For a Blake-stitched pair, find a cobbler with a Blake machine before you need one.

What to buy once, and what to enjoy for a season

Buy once: a black cap-toe or whole-cut oxford in calf, welted if you can; a black derby or monk strap on rubber for weather and long days; a dark brown pair if you wear gray, olive or stone tailoring; and a patent oxford if black tie comes up more than once a year. Enjoy for a season: shoes whose appeal is the hardware or the logo, such as micro studs, engraved buckles and gradient finishes.

How we chose

We sorted shoes by lacing, decoration and sole before we looked at houses, and checked every photograph against its name. Two Kiton pairs sold as oxfords lace open, so we call them derby-laced; Brioni's slip-on, listed simply as leather, photographs with an evening shine, so it sits with the patent pairs. A Tom Ford oxford sold as brown photographs black, a Saint Laurent derby listed as bordeaux photographs brown, and a Manolo Blahnik penny loafer turned out to be two-tone; all three stayed out. Construction appears only where a listing states it, and every pair is new and from a house on Vêtir's luxury list. Browse men's shoes for more.

Frequently asked questions

What color shoes go with a navy suit?

Our stylists choose black: an oxford, derby or monk strap in calf or suede, with a black belt. A clear burgundy is their second option. Vêtir's stylists do not pair brown or tan shoes with navy.

What is the difference between oxford and derby shoes?

The lacing. An oxford's eyelet panels are stitched under the front of the shoe, so the lacing is closed and sleek; a derby's sit on top and open outward, giving more room over the instep and reading slightly less formal.

Are brogues formal enough for a suit?

Quarter and semi-brogues in black or dark calf work with business suits. Full wingtips and longwings belong with flannel, tweed and odd jackets, and no brogue is right for black tie.

What shoes do you wear with a tuxedo?

Black patent or highly polished lace-ups, which is what Debrett's asks for, with black silk socks. A plain patent oxford is the safest choice. Our stylists keep patent pumps and velvet slippers for parties you host or creative black tie, and never pair a monk strap or a thick sole with a tuxedo.

Can dress shoes be resoled?

Goodyear-welted shoes are built for it: the sole is stitched to the welt, so a cobbler can replace it without disturbing the upper. Blake-stitched shoes can be resoled by a cobbler who has a Blake machine, and cemented shoes are the hardest to repair well.

Should new dress shoes feel tight?

Snug, not painful. Laced firmly, an oxford should leave a slim, even gap between its quarters, and the shoe should crease where your foot bends. Read the listing's fit note, since some houses run small and others large.

Keep reading

• Men's tuxedos: what black tie requires
• The best loafers for men
• Men's work outfits for every dress code
• The best men's winter coats to wear over a suit
• The best men's fall boots