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How to match your shoes and trousers

How to match your shoes and trousers

The weather should be the first thing that guides which shoes you slip on in the morning. But the second is what they’ll sit beneath. Matching a jacket and trousers is tricky enough, but you’re at least working in the same ballpark of fabric and colours. But footwear is a different game entirely – you need to think about leather’s shininess or whether the soles are smart enough. Get it wrong and you risk looking like your feet are off to the pub, but your legs are meeting the boss.

To get around that, menswear used to implement hard-and-fast rules – formal trousers needed high-shine Oxfords; trainers were only for sportswear. But things have become flexible recently. “Rules are subjective and there to argue with and break,” says Thread stylist Millie Rich. “But if you’re ever unsure, these two guidelines will help: smart trousers go well with smart shoes, and vice-versa; and lighter trousers pair better with casual shoes.” To help you find the perfect pair, we’ve broken down some pointers for three different types of trousers.


Jeans and trainers

Photographed: MVP jeans (£30); Oliver Sweeney trainers (£199)

 The key concern with denim is colour. “If you opt for a light or distressed pair, then wear them with trainers,” says Millie. “Mid-blue can work with trainers or a desert boot style, and raw denim works with trainers and lace-up boots. Black denim looks great with black Chelsea boots, but never anything smarter than that.” Keep your work shoes for work.


Chinos and brogues

Photographed: MVP chinos (£22); Church’s brogue boots (£359)

In the same way that chinos work with a blazer or a bomber jacket, they go both ways with your shoes. “It’s more about the occasion and the time of year,” says Millie. “In the summer pair with loafers, boat shoes or trainers and in the winter opt for boots or a pair of brogues.” Just make sure the footwear goes with what’s higher up – think blazer with brogues, bomber with trainers.

Tailored trousers

Tailored trousers and derbies

Photographed: Reiss formal trousers (£125); Selected Derby shoes (£75)

Base your shoes on how dressy the trousers are. If they’re part of a suit – or even a tuxedo – stick to smart shoes. But trousers that you could also wear with knitwear offer footwear flexibility. Whatever style you choose, just pick the smartest version in that particular category. “When pairing with trainers, go for a clean, minimal leather style to keep the right side of scruffy,” says Millie. “Tailored trousers also work with boots and an unstructured blazer, because the textures complement each other.”