How to Choose Dress Shoes: The Three Pairs Most Men Need

Most men need three pairs of dress shoes: a black cap toe oxford for suits and formal events, a brown or tan wingtip or derby for chinos through to a navy suit, and a loafer for warm weather and business casual. Buy them in that order, and buy the best leather you can afford. A good pair outlasts three cheap ones.

Which three dress shoes does a man actually need?

Start with a black cap toe oxford. It works with a charcoal suit, a navy suit, and a funeral. The one we sell most often online is the Johnston & Murphy Conard Cap Toe in Black ($225 CAD), a calfskin oxford with a padded footbed, EVA midsole, and rubber outsole.

Second, a brown shoe with some texture. A tan or mahogany wingtip is the pair you will reach for most: chinos, grey flannels, jeans with a sport coat, a navy or mid-grey suit. The Johnston & Murphy Bradford Wingtip Oxford in Tan ($198 CAD) has broguing, a welt midsole trim, and a grip sole.

Third, a loafer. The Johnston & Murphy Hawthorn Bit in Tan ($195 CAD) has leather and mesh linings, a cushioned footbed, and a flexible rubber outsole.

Oxford vs derby vs loafer: what is the difference?

The lacing. An oxford has closed lacing (the eyelet tabs are stitched under the front of the shoe), which makes it sleeker and more formal. A derby has open lacing (the tabs sit on top), which fits a little roomier and looks more relaxed. A loafer has no laces.

If you have a high instep or a wide foot, a derby usually fits better because the open lacing gives you room to adjust.

A monk strap is as dressy as an oxford but closes with buckles. Once you own the three above, the Liam Daniels Double Monk in Brown ($245 CAD, cap toe, European sizes 41 to 46) is a good fourth pair.

Cap toe, wingtip, or plain toe: which is dressier?

Plain toe is the most formal, cap toe is a close second, and wingtip is the most casual. The more stitching and broguing (the punched holes) on a shoe, the more casual it reads. Plain or cap toe for a wedding, an interview, or a dark suit; wingtip for a sport coat, chinos, or a lighter suit.

What colour dress shoes go with a navy, grey, or blue suit?

• Navy suit: brown, tan, or black. Brown is the classic pairing; save black for evening and very formal settings.
• Charcoal suit: black is safest. Dark brown (mahogany, not tan) also works. Light tan against charcoal is too much contrast.
• Light or mid grey suit: brown or tan is best, black is fine for business.
• Lighter blue suit (summer weddings): tan or light brown, never black.
• Black suit or tuxedo: black only.

With chinos, almost anything brown works. Match your belt to your shoes in colour and roughly in finish. We stock belts in the same tans and blacks as the shoes.

When does a rubber sole make sense for a GTA winter?

From November to March in the Toronto area, a rubber sole is the smarter buy. Leather soles breathe well, but they soak up slush, get slippery on wet tile and packed snow, and salt stains the edges. Rubber grips, keeps water out, and needs less upkeep. The Conard and the Bradford above both have one, and they still look like proper dress shoes. If you love leather soles, keep them for dry days and have a cobbler add a thin rubber half-sole.

How should dress shoes fit?

Your heel should not slip, and there should be about a thumb's width between your longest toe and the end. Leather stretches a little in width but never in length, so do not buy short. Johnston & Murphy uses US sizing, and several styles, including the Conard, come in wide widths, which matters if dress shoes usually pinch across the ball of your foot. Liam Daniels uses European sizes. If you are between sizes, call us and we will measure the shoe.

How do I care for dress shoes so they last?

Three habits do most of the work. Rotate, so no pair is worn two days in a row and the leather can dry. Put cedar shoe trees in the moment you take them off. Condition and polish about once a month, and wipe salt marks off the same day with a damp cloth and a splash of vinegar in the water.

Common questions

Can I wear brown shoes with a black suit?

No. A black suit calls for black shoes. Brown with black reads as a mistake, not a choice. If you want to wear brown shoes, reach for a navy or grey suit.

Are loafers formal enough for a wedding?

For a daytime or summer wedding, yes, especially a tan or dark brown leather loafer with a lighter suit. For a black-tie or evening wedding, wear a black oxford. If you are in the wedding party, match the groom.

How much should I spend on dress shoes?

Around $200 to $400 CAD gets you a full-grain or calfskin upper, a cushioned footbed, and a shoe a cobbler can resole. Cheaper shoes usually cannot be repaired, so they cost more per year.

Where to start

If you are buying one pair, make it the Conard Cap Toe in Black, then add a tan wingtip and a loafer as budget allows. Browse everything in stock in our dress shoes collection or the full Johnston & Murphy collection. Shipping is free over $75 in Canada and the US; on US orders, duties may apply to imported brands. Or come see us in Markham and try three pairs side by side.

Read next: Johnston & Murphy dress shoes: sizing and what we carry, A five-day work wardrobe from twelve pieces, and Wedding guest style guide for men.