Types of dress shoes for men, from formal to relaxed

Oxfords: the most formal lace up

An oxford has closed lacing. The two panels that carry the eyelets are stitched underneath the front of the shoe, so when you lace it they meet in a neat V with almost no gap. That clean line is why oxfords are the standard for suits, interviews and formal events. American shoemakers sometimes call the same construction a balmoral, while British makers simply say oxford.

Oxfords come in several faces. The cap toe, with a straight seam across the toe, is the classic business shoe and the safest first pair. A plain toe oxford has no seam at all and looks even sleeker. A wholecut is cut from a single piece of leather with only a seam at the heel; it is minimalist and very formal, and in black it works for evening wear. Oxfords also appear with broguing, which makes them less formal, as explained below. If you are unsure whether your shoes are oxfords, our comparison of oxford vs derby shoes shows how to tell at a glance.

Derbies: the versatile lace up

A derby, often called a blucher in the United States, has open lacing: the eyelet panels are sewn on top of the front, so they can spread apart. That makes the shoe easier to fit over a high instep or a wide foot, and many men find a derby the most comfortable dress shoe for long days. It is a step less formal than an oxford.

A plain or cap toe derby in dark brown is one of the most useful shoes a man can own: sharp enough for a suit, relaxed enough for chinos and jeans. The Norwegian or split toe derby, with a raised seam running around the toe, leans more country and casual. On a derby a thicker sole or a pebbled leather pushes it further toward weekend wear.

Brogues and wingtips

Brogue is not a shoe type so much as a decoration: rows of small punched holes and serrated edges along the seams. It began on country shoes and still signals a more relaxed feel. A quarter brogue adds punching only along the toe cap seam and stays quite formal. A semi brogue adds a decorative medallion on the toe. A full brogue, or wingtip, has a toe cap shaped like a W with wings running down the sides, and is the most casual of the three. A longwing extends those wings all the way around to the heel.

Because broguing can go on either an oxford or a derby, you will see names like wingtip oxford or brogue derby. A brown wingtip is a natural partner for tweed, flannel and odd jackets, and it holds up well with jeans. For the most formal settings, choose a smooth toe instead.

Monk straps

Monk straps close with a buckled strap across the instep instead of laces. The single monk has one strap, the double monk two. They sit between derby and oxford in formality: fine with most business suits and sport coats, but rarely right for black tie. The buckle is the eye catcher, so choose restrained hardware and let the shoe be the one metal accent near your feet. Double monks are the more common modern choice, and some men wear the top strap unbuckled for a casual look; it is a style choice rather than a rule, and it can look sloppy with a suit.

Loafers and dress boots

Loafers are slip ons without laces. The penny loafer with its strap across the vamp is the classic American version, the tassel loafer and the horsebit loafer, introduced by Gucci in 1953, are slightly dressier, and the Belgian loafer and driving moccasin sit at the casual end. A sleek black or dark brown loafer can accompany a lighter business suit, although it is still less formal than a lace up. Our guide to how to wear loafers covers socks and trouser length.

Dress boots fill the same role in colder months. The Chelsea boot, with elastic side panels, is the sleekest and pairs well with slim suits; see how to wear Chelsea boots. The jodhpur boot wraps a strap around the ankle, the balmoral boot has closed oxford lacing, and the chukka, with two or three eyelets, sits at the casual end, with the suede desert boot as its relaxed cousin.

Fancy dress shoes for black tie

What are the fanciest dress shoes called? For black tie, the answer is a patent leather oxford, usually a plain toe, or an opera pump: a low slip on in patent leather or velvet, finished with a flat grosgrain bow. Opera pumps are the most traditional and most formal shoe in menswear, while a highly polished black wholecut or plain oxford is an acceptable alternative for most black tie events. Our black tie guide covers the rest of the outfit. Velvet slippers, often embroidered, are a relaxed option for private evening parties rather than formal dinners.

Which dress shoes to buy first, and comfort

If you own one pair, make it a black cap toe oxford: it covers interviews, funerals, formal weddings and most business suits. The second pair should be dark brown, either a derby or a loafer, which handles business casual, navy and gray suits and jeans. A pair of suede Chelsea or chukka boots covers winter weekends. That combination handles nearly every dress code short of black tie.

For comfort, fit matters more than type. Leave about a thumb's width of room in front of your longest toe, look for a snug heel that does not slip, and try shoes on in the afternoon when feet are slightly larger. Derbies suit high insteps better than oxfords, and a rubber or rubber inlay sole softens walking on hard floors. Our guide to how shoes should fit goes deeper, and the right belt and socks finish the look.

Dress shoes for women, briefly

Women's dress shoes follow a different vocabulary. Pumps, with a closed toe and a heel, are the most formal everyday choice, and a black pump in leather or suede works with almost any dress code. Slingbacks leave the heel open with a strap behind, mules have no back at all, and pointed or almond toe flats give a dressy look for long days on your feet. For comfortable walking, a block heel of around 2 inches (5 cm), a cushioned insole and a secure strap usually do more than any brand promise. Menswear styles such as loafers, oxfords and monk straps are now standard in women's business wardrobes too, and the same formality principles apply to them.