Wearing a suit with sneakers in 2021: a visual guide

The rules of tailoring are always changing, and right now the flow is drifting towards the casual. Get rid of the old and stiff, into aggressively oversized blazers and suits of armor instead of ties. Savile Row got street after decades – even centuries – that customization was treated as sacred. Instead, we realized it can be fun.

The easiest way to change things? Ditching those tired brogues and Oxfords, and wearing a suit and sneakers instead. It’s a look that has become a bit ubiquitous in recent years, part of the inevitable streetwear takeover that has infiltrated every corner of menswear.

In the same way that minimalist sweatshirts are now suitable for office wear, it is perfectly acceptable to combine sneakers with formal. It’s not as easy as just putting on a few Converses, 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?

Formal dress is, and always has been, about rules. Some you can break, others are very strong and it is important to know which is which. If you are going to an event where the dress code is indicated, pay close attention. Anything formal – from black tie to business attire – should be followed to 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 at all, then sneakers are fair game. If it’s a laid-back wedding, a relaxed office environment, or just a party you want to spice up your mind for without turning things up a notch, read on, my friend.

Who should try it?

Everyone, 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 reserved for the man cycling to the office, or the uncle with orthopedic problems, but not anymore.

This is an incredibly versatile look – one that’s cool and youthful, but it’s suitable 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 pants, for obvious reasons. The most infallible are those with a slender leg and a regular or slightly shorter length. The pants should ideally cushion the top of your shoe, with a strip of ankle. At the top, a single-breasted jacket with a narrow lapel is an easy win. Double breasted jackets can also work, but stick to the four-button, low-button versions as they look more casual.

Rules are there to be broken, of course. If you’re a fan of the oversized look, you can channel it through tailoring. Shady wide-leg pants with a significant break in them (where the hem hits 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 pants.

Just remember to keep it purposeful – you don’t want to look like you ransacked your dad’s wardrobe.

Style everything else down too

Channels

Wearing sneakers with your suit is an excellent excuse to drop the tie. Wear your shirt tucked in, but with the top few buttons unbuttoned. Or throw the shirt away completely and put a clean T-shirt, knitted polo shirt or crew neck sweater under your jacket.

Be smart with color

travel

A sleek, 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 go with just about any suit color — bright blue, emerald green, or moody burgundy are all surprisingly easy to wear.

If you’re going for colorful kicks, opt for light pastels, navy blue and khaki. Steer clear of black sneakers with dark suits, which look a bit schoolboy, and don’t forget to keep that delicate smart-casual balance by wearing a more muted suit with louder shoes.

Try breakups

suit supply

Divorces are still highly underestimated when it comes to low-key smart dressing. The trick is to invest in good separates designed to be just that, not just mix and match suits. The classic combos are gray and navy or gray and black, but you can also try tonal blazers and trousers — blue on blue, green on green — or pair a brighter piece with a more neutral partner.

These all look neat with minimal leather sneakers.

The best trainer styles to wear with suits

Minimalist Sneakers

Everything changed with the Achilles Low from Common Projects. This sleek leather shoe had minimal detailing, but was crafted with the care usually reserved for Northamptonshire brogues. The style has been copied far and wide and the simple design lends itself perfectly to dressy tailoring.

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

Retro sports shoes

We’re mainly talking throwback tennis shoes here, but old-school runners and even skate shoes can work with the right styling. Thicker, with more panels and retro details like perforations or gum soles, this offers a different aesthetic than tailoring. Less Scandinavian minimalism and more Wes Anderson – indie and playful, but also considered.

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

Chunky Sneakers

A word of warning: This is not an easy look to create. Wear a chunky sneaker with a suit and you can look like a banker commuting in his running shoes because his Oxfords are too uncomfortable. Lean very modern with the suit: unstructured, boxy, intentionally subversive. And keep the sneakers muted in color if they’re flashy in proportion.

High peaks

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

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

Ways to wear sneakers with a suit

Tonal

Cornelian

Going on stage is one of those classic styling tricks that makes a guy look like he knows what he’s doing – and it’s so easy. Off-white and gray are great for summer, but you can achieve the same effect with shades of khaki, brown, even pink and yellow, if you feel like it.

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

Modern

Todd Snyder

Don’t be afraid to play with classic menswear fabrics, such as a pinstripe or Prince of Wales check. Often these come from heavier wool, which, when worn with sneakers, looks almost tracksuit-like.

Stick to subtle patterns and a slim, single-breasted cut, layer your suit over a t-shirt or sweater to keep it casual. Dark stairs work well here, complementing the visual weight of the look.

Neutral

travel

In the warmer months, unstructured, lightweight cotton and linen suits are an absolute lifesaver and a perfect opportunity to dress things up a bit. A white T-shirt (one you keep for special occasions, not the one you keep in your gym bag) and ever so light retro sneakers are really all you need.

Relaxed

Windsor

Suits with a looser, more regular fit are excellent candidates for relaxed, workwear-style styling. Namely: robust (but still minimal) sneakers and an Oxford shirt opened over a crew-neck T-shirt. Look for a jacket with patch pockets that instantly reads as casual, and keep your color palette subtle and sleek.

Colorful

suit supply

About as classic as they come, this suit is testament to how easy it is to wear tailoring with sneakers. The vibrant blue makes the tailoring immediately more playful, but the knitted polo and silk pocket square ensure that it retains a chic edge.

Dressed

boglioli

A chambray shirt! With a suit! Now you are playing with fire. Actually, mixing a denim-like texture is a smart way to dress up a suit — like wearing a blazer with jeans, but smarter. Be smart with your color combinations: khaki goes 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

In recent years there has been a resurgence of double breasted suits, and they look good when done right. You want the cut to be more Beckham than banker – form-fitting throughout, not too loose in the lapel and not too long in the jacket (the bottom hem should reach over your bum, not dangle along).

Go for block colors or, as we have here, a subdued mottled texture. A suit like this can only be dressed up to a point, so keep it fresh with an open-neck shirt and leather shoes.

the staple pack

Brunello Cucinelli

If you’re the type who only wears a suit once or twice a year, you’ll want to stick with the classics – and a mid-gray two-button version might just be the most versatile of them all. It’s all about the details here: the notch lapel is naturally less formal, and the turn-up of the pants is almost begging to be worn with a new pair of leather sneakers (loafers are great with these types of pants too, but that’s for another time).

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

Linen

Todd Snyder

Linen suits get a bad reputation: crumpled, ill-fitting and misshapen. But as with everything in life, it’s all about quality, and today’s designers are creating two-piece linen pieces that look as cool as they feel. The key is to work with the fabric: accept that it’s prone to the odd creases and lean into the casual vibe.

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

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