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What’s This About

The main dress shoes are the Oxford, Derby, monk strap, brogue, loafer and wholecut, and the right choice depends on the dress code and the fit.

This guide explains how to choose and wear dress shoes, such as

The difference between Oxfords and Derbies

What a Goodyear welt is and why it allows resoling

How formal each dress shoe type is

Outfit ideas for black tie, business casual and summer weddings

The five pairs to buy first

and many more!

Buy for the occasions you actually dress for, choose shoes that fit, and look after them so they last.

Key Points

01Oxfords have closed lacing and are the most formal lace-up shoe, while Derbies have open lacing and are more versatile.

02Goodyear-welted shoes can be resoled many times, which is why they are often a long-term buy.

03Black Oxfords and dark brown Derbies cover most occasions for a first collection.

04Comfort and fit matter as much as the design; never accept shoes that pinch in the shop.

Dress shoes are the leather shoes you wear with tailoring, from a dinner suit to a blazer and chinos.

Choosing them well comes down to three questions, which are how formal the shoe is, whether it fits, and whether it suits the clothes you actually wear.

This guide explains the main types of dress shoe, how formal each one is, how to wear them, and which pairs to buy first if you are building a small collection.

What are dress shoes?

Dress shoes are leather shoes made to be worn with suits, tailored trousers and formal or smart casual outfits.

Most have a slim leather or thin rubber sole, a low heel and a smooth or lightly textured upper.

Collage of men's leather shoes worn with tailored trousers, including loafers, brogues, two-tone shoes and boat shoes

Good dress shoes are usually made of calf leather or suede, with a sole that is stitched rather than only glued.

Comfort and good looks are not a trade-off in a well-fitted pair, so fit matters as much as the design.

The Goodyear welt and how dress shoes are made

Many traditional dress shoes are Goodyear-welted.

A strip of leather, the welt, is stitched to the upper and the insole, and the outsole is then stitched to the welt, with a layer of cork filling the space underneath.

The method is named after Charles Goodyear Jr, who invented the machinery that made it practical.

Because the welt sits between the upper and the sole, a cobbler can replace a worn sole without damaging the upper, so a welted shoe can be resoled many times.

Blake-stitched shoes, common in Italy, have the sole stitched directly to the upper, which makes them lighter and more flexible, and they can also be resoled by a specialist.

Shoes with glued soles are usually cheaper and lighter, but they are harder to repair.

Dress shoe types at a glance

The table below compares the main dress shoe types by their key features and how formal they are, with a less formal alternative for each.

Dress shoe	Key features	Formality	Less formal alternative
Oxford	Closed lacing, sleek shape	Highest	Derby
Wholecut	Upper cut from a single panel of leather	Highest	Plain or cap-toe Oxford
Derby	Open lacing, slightly roomier	High to medium	Suede Derby or chukka boot
Monk strap	Buckle closure, no laces	High to medium	Loafer
Brogue	Decorative perforations	Medium to high	Suede brogue
Loafer	Slip-on, no laces	Medium	Driving loafer

Brogueing is a decoration rather than a shoe of its own, so a brogue can be an Oxford or a Derby; the more perforations, the more casual it looks.

Why the right dress shoes help

Shoes finish an outfit, so a clean, polished pair that suits the dress code makes the rest of your clothes look more considered.

Workplaces and events often have dress codes, and knowing which shoe each one expects saves you from guessing on the day.

Shoes that fit well are more comfortable to wear for a long day, which makes it easier to stand, walk and stop thinking about your feet.

A small collection of well-chosen pairs covers most occasions, from business formal to weekends.

Welted shoes that are looked after and resoled can last for many years, though price on its own does not tell you how well a shoe is made.

Oxford shoes

Collage of black and brown cap-toe Oxford shoes worn with tailored trousers

Key features	Best for	Formality
Closed lacing, sleek shape	Formal events, business formal attire	Highest

An Oxford has closed lacing, which means the vamp, the front of the shoe, is stitched over the two side panels that carry the eyelets, so the eyelet tabs sit under the vamp and close neatly when laced.

That clean, close shape is why Oxfords are the standard shoe with a dark suit and with black tie.

Our guide to Oxford shoes explains the main Oxford types and how to wear each one.

Oxfords for a formal look

For a black tie charity dinner, start with black Oxfords in highly polished calf leather or patent leather.

Man in a black dinner suit, white dress shirt and black bow tie, with black Oxford shoes

Wear them with a black or midnight blue dinner suit with peak or shawl lapels.

The trousers should have little or no break, just touching the top of the shoes.

Choose a white dress shirt with a pleated or marcella bib front and double cuffs.

Finish with plain cufflinks, a black silk bow tie and a white linen pocket square.

Derby shoes

Collage of tan, burgundy and brown suede Derby shoes worn with tweed, corduroy and cream trousers

Key features	Best for	Formality
Open lacing, slightly more relaxed look	Business casual, smart casual events	High to medium

A Derby has open lacing, meaning the side panels carrying the eyelets are stitched on top of the vamp, so the two flaps can open wider.

That makes a Derby easier to fit over a high instep and gives it a slightly more relaxed look than an Oxford.

In the US, a Derby is often called a Blucher; strictly, a Blucher has small eyelet tabs sewn onto a vamp cut as a single panel, but the two names are widely used for the same open-laced shoe.

A plain black Derby can be worn with a suit, and a brown Derby suits business casual and smart casual settings.

Derbies for a business casual look

For a client lunch where you want to look smart but approachable, start with dark brown Derbies in smooth or burnished leather.

Wear them with navy chinos or wool trousers, with a short break or a neat hem.

Add a light blue Oxford cloth button-down shirt with the top button undone.

Layer an unstructured oatmeal blazer on top.

Finish with a brown leather belt close in tone to the shoes and a muted paisley pocket square.

Monk strap shoes

Collage of black and brown single and double monk strap shoes with tailored trousers

Key features	Best for	Formality
No laces, buckle closure	Business attire, smart casual and social events	High to medium

Monk strap shoes close with one or two buckled straps instead of laces.

A black or dark brown single monk with a plain toe is close to an Oxford in formality, while a double monk or a lighter colour looks more relaxed.

Monk straps for a creative look

For a gallery opening, start with burgundy double monk strap shoes in polished leather.

Wear them with charcoal wool trousers with a tapered leg.

Add a white dress shirt and a charcoal waistcoat that matches the trousers.

Layer a softly structured forest green blazer on top.

Skip the tie, add a silk pocket square in burgundy and green, and wear a small vintage-inspired lapel pin if you like.

Brogue shoes

Brown wingtip brogue with decorative perforations, worn with black socks and check trousers

Key features	Best for	Formality
Decorative perforations, Oxford or Derby lacing	Business casual, smart casual events, weekends	Medium to high

Brogues are shoes decorated with rows of small perforations, called brogueing, along the seams and often on the toe.

Their roots are usually traced to country shoes from Scotland and Ireland, which is one reason brogues still look at home with tweed and flannel.

A quarter brogue has perforations only along the toe cap, a semi-brogue adds a pattern on the toe, and a full brogue, or wingtip, has a toe cap shaped like a W that runs along the sides.

Brogues for a smart casual look

For a weekend garden party, start with tan suede wingtip brogues.

Wear them with sage green chinos, hemmed to show a little sock.

Add a white poplin shirt under a cream cable-knit jumper.

Layer a navy wool and linen blazer on top.

Finish with a woven leather belt and a small floral pocket square.

Loafers

Collage of black penny loafers, brown tassel loafers and brown penny loafers worn with tailored trousers

Key features	Best for	Formality
Slip-on, no laces, often with a strap, tassels or a metal bit	Business casual, smart casual events, summer suits	Medium

Loafers are low-cut slip-on shoes with no laces.

Penny, tassel and horsebit loafers are the most common dress styles, and our guide to loafer types explains each one.

Loafers for a summer suit

For a summer wedding with a smart, daytime dress code (not black tie), start with burgundy or dark brown penny loafers in polished leather.

Wear them with a light grey tropical wool suit, with the trousers hemmed to show a little ankle.

Add a pale pink or white shirt.

Choose a light silk tie if the invitation suggests one, or a silk pocket square in burgundy, pink and grey if ties are optional.

Check the invitation first, because a formal or black tie wedding calls for Oxfords instead.

Wholecut shoes

Key features	Best for	Formality
Upper cut from a single panel of leather, with only a seam at the heel	Formal events, business formal, evening wear	Highest

A wholecut has an upper cut from a single panel of leather, so the only visible seam is usually at the back of the heel.

The plain surface shows off the leather and the shape of the last, which makes a wholecut look very sleek and formal.

Wholecuts for a business formal look

For an important board meeting, start with black wholecut shoes polished to a high shine.

Wear them with a charcoal grey three-piece worsted wool suit.

Add a white dress shirt with a spread collar.

Choose a deep burgundy silk tie with a subtle herringbone pattern and a white linen pocket square folded square.

British, Italian and American dress shoes

Shoes from different countries often follow different traditions, though every maker varies.

In Britain, Northampton makers such as Church’s, founded in 1873, are known for Goodyear-welted shoes with rounded toes and sturdy soles, and John Lobb has made bespoke shoes in London since the nineteenth century.

In Italy, many makers favour sleeker shapes, longer toes and lighter construction, often Blake-stitched.

American makers such as Allen Edmonds, founded in Wisconsin in 1922, often sit between the two, with roomier fits and welted soles.

Essential dress shoes to start a collection

You do not need many pairs to cover most occasions; start with the shoes that match the clothes and dress codes you meet most often.

Shoe type	Colour	Why start here	Occasions
Oxford	Black	Covers the most formal dress codes	Formal events, business formal, interviews
Derby	Dark brown	Works with suits and with chinos	Business casual, smart casual
Brogue	Tan or mid-brown	Adds texture for less formal outfits	Smart casual, weekends
Loafer	Burgundy or dark brown	Easy slip-on for warm weather and casual offices	Business casual, summer events
Monk strap	Brown	A laceless alternative to the Derby	Business casual, social events

Black Oxfords

Black Oxfords are the safest first pair if you wear suits or attend formal events, because they suit interviews, funerals, weddings and black tie.

Choose a plain or cap-toe design with little decoration so they work across all of those occasions.

Dark brown Derbies

Dark brown Derbies cover the widest range of everyday outfits.

They are smart enough for most business settings and relaxed enough for chinos and a jumper.

Tan brogues

Tan or mid-brown brogues add texture and colour to smart casual outfits, especially in spring and summer.

They go well with navy and mid-grey suits worn in a relaxed way, and with chinos.

Burgundy loafers

Burgundy loafers are comfortable for warm weather and casual offices.

They suit chinos and a blazer, and they also work with dark jeans; our guide to dress shoes with jeans shows how.

Brown monk straps

Brown monk straps are a laceless alternative to the Derby for business casual and social events.

Single and double strap versions are both easy to wear; the double strap is a little more noticeable.

Later additions

Once the basics are covered, you might add

Patent leather Oxfords for black tie, or velvet slippers for relaxed black tie evenings, especially at home

Suede loafers for summer weekends

Wholecuts for formal business settings

Two-tone spectator shoes for a vintage-inspired summer look

Dress shoe do’s and don’ts

Do	Don’t
Wear a belt close in colour to your shoes	Wear thick athletic socks with dress shoes
Hem trousers so they sit neatly on the shoe	Leave shoes scuffed or unpolished
Rotate your shoes and use cedar shoe trees	Wear the same leather pair every day
Choose the shoe for the dress code	Ignore the dress code on the invitation
Buy for fit and construction, not price alone	Accept shoes that pinch in the shop
Check laces, heels and soles regularly	Wear patent evening shoes with casual clothes
Choose materials for the season	Wear formal Oxfords with shorts or sportswear

Wear a belt close in colour to your shoes

A belt in the same colour family as your shoes makes an outfit look consistent.

The match does not need to be exact. A dark brown belt with dark brown shoes or a black belt with black shoes is enough.

Hem trousers to the right length

The break is the fold where your trouser leg meets the shoe.

A slight break or no break keeps a clean line and shows the shoe, while a deep break bunches fabric over it; which you choose is a matter of taste, as long as the hem sits neatly.

Rotate your shoes

Leather absorbs moisture from your feet, so giving a pair a day’s rest with cedar shoe trees helps it dry and keep its shape.

Having two or three pairs you can alternate makes each one last longer.

Wear dress socks

Thick athletic socks look bulky with slim leather shoes.

Thin wool or cotton socks that match your trousers continue the line of the leg, and a subtle pattern is fine with less formal outfits.

Final thoughts

Start with the dress codes you meet most often, buy shoes that fit, and look after them so they last.

A black Oxford and a dark brown Derby cover most needs, and loafers, brogues and monk straps add variety as your wardrobe grows.

Sources

Tricker’s, Goodyear welting (construction, resoling, Charles Goodyear Jr).

E.J. Daniels, The Derby Shoe and Blucher Guide, Gentleman’s Gazette, 2014, updated 2023 (Oxford, Derby and Blucher lacing).

Church’s, Wikipedia (founded 1873, Northampton).

Dress Shoes Guide for Men, the Types, How Formal Each One Is and How to Wear Them