Shoes
Men's Shoe Types Explained: Oxfords, Derbies, Loafers, Monks & More
A clear guide to every classic men's shoe: oxfords, derbies, brogues, loafers, monk straps, boots and sneakers. What they are, and which outfits they go with.
Style Guide
Which Shoes to Wear With Every Style
Oxfords, derbies, loafers, boots and sneakers: which men's shoes go with which outfits, and how to build a shoe collection that covers everything.
Shoes: all guides
2 in-depth articles in this section.
Shoes
Men's Boots Guide: Chelsea, Chukka, Work Boots & How to Wear Them
Every men's boot style explained: chelsea, chukka, desert, brogue, service, moc-toe and combat boots, with which outfits and styles each one suits.
Shoes make or break the outfit
Shoes are usually the first thing people notice and the last thing men think about. A great suit with scuffed square-toed shoes looks cheap, and a plain t-shirt and jeans with clean leather boots looks put together. The shoe sets the formality of the whole outfit.
Shoe and style pairing chart
| Style / outfit | Best shoes | Avoid |
|---|---|---|
| Black tie / tuxedo | Black patent or highly polished oxfords, velvet slippers | Brogues, brown shoes |
| Business suit | Black or dark brown cap-toe oxfords, plain derbies | Sneakers, heavy boots |
| Smart casual | Loafers, suede derbies, chelsea boots, minimal leather sneakers | Running shoes |
| Casual (jeans, tees) | White leather sneakers, chukkas, desert boots, canvas sneakers | Shiny formal oxfords |
| Sport-classic | Premium leather sneakers, suede loafers | Chunky trainers |
| Heritage / workwear | Moc-toe boots, service boots, brogue boots | Sleek dress shoes |
| Summer / resort | Loafers without socks, espadrilles, boat shoes | Heavy boots |
| Golf | Spikeless golf shoes, soft-spike classics | Street sneakers on the course |
The five-pair shoe collection
You can cover almost every situation with five pairs: black cap-toe oxfords for formal events, brown derbies or loafers for business and smart casual, suede chelsea or chukka boots for autumn and winter, white leather sneakers for casual days, and one sturdy pair of leather boots for rain and heritage outfits.
Explore our shoe guides
Learn every classic style in men's shoe types explained, and choose the right boot with our men's boots guide. Don't forget the layer in between. Our socks section explains how to match socks to shoes and trousers.