Breaking The Rules: How To Wear A Suit With Sneakers

The rules of tailoring are always in flux, and right now the current is drifting toward the casual. Out with the old and rigid, in with aggressively oversized blazers and body harnesses in lieu of ties. Savile Row got street after decades – centuries even – of tailoring being treated as sacred. Instead, we realised it can be fun.

The simplest way of switching things up? Ditching those tired brogues and Oxfords, and wearing a suit with sneakers instead. It’s a look that’s become somewhat ubiquitous in recent years, part of the unavoidable streetwear takeover that’s infiltrated every corner of menswear.

In the same way that minimalist sweatshirts are now suitable office wear, it’s perfectly acceptable to do sneakers with formal. It’s not as simple as just chucking on a pair of Converse, but as long as you follow a few simple rules, it’s an easy look to pull off. Promise.

When Can You Wear Sneakers With A Suit?

Formalwear is, and has always been, about rules. Some you can break, others are iron-clad, and it’s important to know which is which. If you’re going to an event where the dress code has been specified, pay close attention. Anything formal – from black tie to business dress – is to be adhered to by the letter, which means wearing appropriate footwear.

But, if you’ve been encouraged to dress casually – including smart-casual – or if there’s no expectation whatsoever, then sneakers are fair game. If it’s a laid-back wedding, a relaxed office setting, or just a party that you want to smarten up for without going the whole hog, then read on, my friend.

Who Should Try It?

Anyone, regardless of style, size or shape. You – yes, you, reading this – can wear sneakers with a suit. There was a time when such a look was the preserve of the guy who cycles into the office, or the uncle with orthopaedic problems, but not any more.

This is an incredibly versatile look – one that’s cool and youthful, but works for any age and any style.

Suits with Sneakers Guidelines

The Cut

Brunello Cucinelli

Sneakers only work with suits that have the right cut. We’ll start with trousers, for obvious reasons. The most foolproof are those with a slim leg and regular or slightly cropped length. The trouser should ideally kiss the top of your shoe, showing a sliver of ankle. Up top, a single-breasted jacket with a slim lapel is an easy win. Double-breasted jackets can work too, but stick to four-button varieties with a low button stance, as these look more casual.

Of course, rules are meant to be broken. If you’re a fan of the oversized look, you can channel this through tailoring. Louche, wide-legged trousers with a proper break in them (where the hem falls against the shoe, creating a crease in the fabric) are excellent with chunky sneakers and a regular fitted jacket. The same goes for boxy, oversized jackets with slimmer, cropped trousers.

Just remember to keep things purposeful – you don’t want to look like you’ve been raiding your dad’s wardrobe.

Style Everything Else Down Too

Canali

Wearing sneakers with your suit is an excellent excuse to ditch the tie. Wear your shirt tucked in, but with the top few buttons undone. Or, ditch the shirt entirely and layer a clean T-shirt, knitted polo shirt or crew-neck jumper under your jacket.

Be Clever With Colour

Reiss

A sharp, lightweight suit in black or navy worn with clean white leather tennis shoes looks effortless in that minimalist, Scandi-cool way. Indeed, white or cream sneakers work with pretty much any shade of suit – bright blue, emerald green or moody burgundy are all surprisingly easy to wear.

If you’re going for colourful kicks, stick to light pastels, navy and khaki. Steer clear of black sneakers with dark suits, which looks a little bit schoolboy, and remember to keep that delicate smart-casual balance by wearing a more muted suit with louder shoes.

Try Separates

Suitsupply

Separates are still highly underrated when it comes to low-key smart dressing. The trick is to invest in proper separates designed to be just that, not to just mix and match suits. The classic combos are grey and navy or grey and black, but you can also try tonal suit blazers and trousers – blue on blue, green on green – or pairing one brighter piece with a more neutral partner.

All of these look smart with minimal leather sneakers.

The Best Trainer Styles to Wear with Suits

Minimalist Sneakers

Everything changed with the Achilles Low by Common Projects. This sleek leather shoe was minimal in details but made with the care usually reserved for Northamptonshire brogues. The style was copied far and wide and the simple design lends itself perfectly to dressed-down tailoring.

Beyond white, check out navy and other neutral styles as well as playful tweaks on the classic silhouette from the likes of Zegna, Oliver Cabell and Axel Arigato.

Retro Sports Shoes

We’re mainly referring to throwback tennis shoes here, but old-school runners and even skate shoes can work with the right styling. Chunkier, with more panelling and retro details like perforations or gum soles, this offers a different aesthetic to tailoring. Less Scandi minimalism and more Wes Anderson – indie and playful, but considered too.

Adidas Stan Smiths are an easy way to try this look out. The same goes for Continentals and Supercourts. More adventurous styles include Nike’s retro runners or Vans. Keep the palette to two or three colours max.

Chunky Sneakers

A warning: this one is not an easy look to pull off. Wear a chunky sneaker with a suit and you can end up looking like banker who commutes in his running shoes because his Oxfords are too uncomfortable. Lean very modern with the suit: unstructured, boxy, deliberately subversive. And keep the trainers muted in colour if they’re garish in proportion.

High-Tops

With a cropped and turned-up trouser hem, high top sneakers bring something fresh to tailoring. Yes, it’s a bit Doctor Who but wear a rugby top or cricket jumper instead of a shirt and the look starts to come together.

Converse Chuck Taylors are the obvious choice, but you could also try something like a Nike Blazer Mid, or check out minimal designs from the likes of ETQ. or Novesta. One note: they’ll need to be box fresh, or at least look it. Your battered 10-year-old All Stars won’t cut it.

Ways To Wear Sneakers with a Suit

Tonal

Corneliani

Going tonal is one of those classic styling tricks that makes a man look like he knows what he’s doing – and it’s so easy. Off-whites and greys are great for the summer, but you can achieve the same effect with shades of khaki, brown, even pinks and yellows, if that takes your fancy.

Choose pieces in different but complementary shades of the same colour, with either tonal sneakers (and socks, if required) or neutral footwear.

Modern

Todd Snyder

Don’t be afraid of playing with classic menswear fabrics, like a pinstripe or Prince of Wales check. Often, these will come in heavier-weight wool, which, when worn with sneakers, looks almost tracksuit-like.

Stick to subtle patterns and a slim, single-breasted cut, wearing your suit over a T-shirt or sweater to keep things casual. Darker kicks work well here, to complement the visual weight of the look.

Neutral

Reiss

In the warmer months, unstructured, lightweight cotton and linen-blend suits are an absolute life-saver, and offer a perfect opportunity to dress things down a little. A white T-shirt (one that you save for special occasions, not the one that lives in your gym bag) and ever-so-slightly retro sneakers are really all you need.

Relax

Windsor

Suits with a looser, more regular fit are prime candidates for relaxed, workwear-esque styling. Namely: robust (but still minimal) sneakers and an Oxford shirt layered open over a crew neck tee. Look for a suit jacket with patch pockets, which instantly reads as more casual, and keep your colour palette subtle and tight.

Colourful

Suitsupply

This suit is about as classic as they come, and is proof of how easy it is to nail wearing tailoring with sneakers. The vibrant blue instantly makes the tailoring feel more playful, but the knitted polo and silk pocket square help it retain a smart edge.

Dressed Down

Boglioli

A chambray shirt! With a suit! Now you’re playing with fire. Actually, mixing in denim-like texture is a clever way of dressing down a suit – like wearing a blazer with jeans, only smarter. Be clever with your colour combinations: khaki works well with indigo, as does stone with lighter washes of blue in the summer.

Stick to navy sneakers to keep the palette clean.

Double Breasted

Brunello Cucinelli

There’s been a resurgence in double-breasted suits in recent years, and they look the business when done right. You want the cut to be more Beckham than banker – slim-fitting all over, not too wide in the lapel and not too long in the jacket (the bottom hem should be skimming your bum, not dangling past it).

Go for block colours or, as we have here, an understated mottled texture. A suit like this can only be dressed down to a certain extent, so keep it crisp with an open-necked shirt and leather kicks.

The Staple Suit

Brunello Cucinelli

If you’re the type who wears a suit just once or twice a year, you want to stick to the classics – and a mid-grey, two-button version is perhaps the most versatile of them all. It’s all about the details here: the notch lapel is inherently less formal, and the trouser turn-up is practically begging to be worn with a fresh pair of leather sneakers (loafers are great with this sort of trouser, too, but that’s for another time).

The slight sheen on the wool means you want to keep this fairly smart – a shirt, worn with the top few buttons open, or a merino knit.

Linen

Todd Snyder

Linen suits get a bad rep – crumpled, ill-fitting and misshapen. But as with anything in life it’s all about quality, and today’s designers are whipping up linen two-pieces that look as cool as they feel. The key is to work with the fabric: accept that it will be prone to the odd crease, and lean into the nonchalant vibe.

Darker colours – black, even – bring linen bang up to date, and are more forgiving. Keep everything else super relaxed: canvas shoes, a well-fitting T-shirt or sweater and a good dose of swagger.