How to match your shoes with your suit

We ask the tailoring experts at Chester Barrie how to master formal footwear

There’s one thing that, time after time, we see ruining suits. They could be double-breasted, peak-lapelled, single-vented – it doesn’t matter. Even the most meticulously-tailored two-piece in the world could be sartorially scuppered by being paired with the wrong shoes.

You may not think that shoes are as important as, say, finding the right tie or shirt to match your suit – but you’d be wrong. Your shoes are, almost literally, the foundation on which you build your outfit. As such, we turned to the masters of tailoring across at Chester Barrie to pull together the foolproof guide to matching your shoes with your suit.

Step 1: Matching the Style

“A barrister will wear his navy suit with a different shoe than an advertising exec, even if they both wear them for work,” begins Simon Kirby, Creative Director at Chester Barrie. “It all depends on the occasion and the general circumstances.”

"It all depends on the occasion and the general circumstances..."

Your style, then, depends on what suit you’re wearing and why you’re wearing said suit. Derbys, Oxfords and Brogues are always safe bets, with Monkstraps also a solid choice. Things start to get more difficult when you try pairing boots with suits – so, to avoid any clashes, stay away. And what about trainers?

“As always, this depends” says Kirby. “Luxury brands like Church’s and Prada produce luxury trainers that require a different approach than your favourite, 10-year-old Adidas Gazelles. My advice would be don’t wear the latter with your suit if you are over 21.”

Step 2: Matching the Colour

“Your outfit is a whole – and these individual elements need to be balanced carefully,” says Kirby. “This will require a combination of matching and contrasting various elements. If you are head-to-toe in grey, a contrasting tan shoe can give the much needed contrast.

“But, if you are wearing a jacket/trouser/shirt combination of contrasting colours, you probably do not want to introduce yet another colour with your footwear. That said, black is the only suit colour you should never experiment with.”

In short, use your head. Black goes with everything, brown goes with a navy, blue or light grey suit, tan goes with blue or light grey, and oxblood goes with brown, charcoal grey or navy. Got that?

Step 3: Matching your wider accessories

It’s not just your shoes that matter. Your pocket square, belt and even tie pin can cause problems if not matched properly with your suit. But there’s only one steadfast rule here, Kirby says.

“Your outfit is a whole - and these individual elements need to be balanced carefully...”

“If you are wearing a classic leather belt it should match your shoe colour,” says the expert.

“Although,” he adds, “this rule seems to get relaxed more and more, especially where more casual materials like suede are concerned.”

Further Reading