22 Menswear Trends To Know In 2021

There’s a common misconception that religiously adhering to trends equates to good dressing. In our humble opinion, this is not the case. Blindly following each and every seasonal trend is a recipe for poor style. Not to mention an easy way to bankrupt yourself.

The key to retaining your sartorial self-respect lies in the ability to successfully differentiate between the fleeting fads and the future classics. And in order to give you a nudge in the right direction, we’ve created a carefully selected edit of the menswear movements worth incorporating into your wardrobe this year.

From the return of florals to the continued widening of silhouettes, these are the men’s fashion trends to embrace in 2021.

Spring/Summer 2021


Todd Synder

A return to the 1970s has been one of the overarching trends of the last five years, and it shows no sign of slowing down in 2021. For the spring/summer season, it manifests itself as floral prints a la grandma’s curtains, which is actually a lot more wearable than it sounds.

Everyone from Tom Ford to Burberry has been at it, splashing bold florals onto shorts, vacation shirts and tailoring amongst others. But we’d suggest keeping it to one statement piece per outfit and, as always, ensuring the rest of your look is nice and muted.

Bermuda Shorts

Orlebar Brown

Who likes short shorts? Well, not D&G, Gucci and a plethora of other tastemaking high-fashion houses. Not if their SS21 shows were anything to go by. This season we’ll be seeing the return of longer, wider shorts, echoing a broader shift that has been taking place across all areas of menswear for some time now.

The key to nailing it is making sure you get the length just right. Aim for a couple of inches above the top of the kneecap and opt for tailored styles that can be paired with either casual or smarter pieces with ease.

Relaxed Tailoring


As we move further into the 2020s, breezy silhouettes will continue to eclipse slim, form-fitting cuts. It’s a resurgence of the styles popular in the 1980s and 1990s that has been on the up for some time now and while it may not be everyone’s cup of tea, it can look great when executed well.

If you’re thinking about taking a walk on the wide side yourself, our main advice to you would be to pay your local tailor a visit. Relaxed cuts can still be flattering, but only when they fit properly.

More Gorpcore


High fashion and the great outdoors began flirting a few years ago. Now they’re shouting from the rooftops declaring their love for one another. Fashion journos labelled it ‘gorpcore’ (gorp being a colloquial term for trail mix, or ‘good old raisins and peanuts’) but whatever you want to call it, it looks like it’s here to stay.

Recently, we’ve seen collaborations like Palace x Arc’teryx and Gucci x The North Face, further cementing fashion’s relationship with outdoor gear. But if you want to get involved, we’d suggest working the odd outdoor-inspired piece into your outfits here and there as opposed to going full cosplay mountaineer.

Vertical Stripes


The reasons for embracing the vertical stripe trend are twofold: firstly, it looks great and presents a simple, refined way to experiment with prints; secondly, it has the nice added bonus of shaving a few pounds off your appearance, making you appear taller and slimmer.

For bonus points, opt for styles with stripes of varying width. Or simply stick to classic stripes, or even seersucker, if you prefer to keep things subtle.

Get Nautical

James Dean in a classic Breton top

Menswear has long been looking to the seas for inspiration. You only need to look at the peacoat for evidence of that. But this year it’s going to go to the next level as fisherman beanies, Breton tops and other dock-worker staples creep further into mainstream men’s fashion.

It’s a subgenre of workwear that fashion journalists are already cringingly referring to as “shipster”. But while you may not want to dress in it from head to toe, a couple of its key pieces here and there is a good way to bring your wardrobe up to speed.

Mid-Wash Denim

Brunello Cucinelli

Dark or raw denim is a bona-fide menswear staple. But when the weather turns hot, it ceases to be practical.

Luckily, this season there is a solution to the problem. It’s a few shades lighter, it’s casual and it goes with almost everything. Mid-wash denim was everywhere in the menswear collections and this time it looks as though it could be here to stay.

Warm-Weather Layering


Piling on layers when the sun is shining may not sound like the most practical move to make but it can still be an option if done cleverly. Swap out the heavy outerwear for lightweight jackets and overshirts worn over plain tees, polos or summer-ready shirts. This way you can remove them if you get too hot. Then simply tie them around your waist, shoulders or torso to retain the visual element without the added warmth.

Camp Collar Shirts

Orlebar Brown

Classic collar short-sleeve shirts can carry with them some unwanted “lads down the pub” connotations for some. This breezy summer option offers a stylish way around that. Camp collar shirts have been big for several years now, meaning you can rest assured they have some longevity in them and aren’t just a fleeting fad.

The flat, lapel-style collar adds a touch of something different to what might otherwise be a bland outfit, creating a subtle focal point to tie a look together. Perfect when worn with tailored swim shorts for a light lunch at a beachside restaurant. This year, keep an eye out for long-sleeve versions for a twist on the norm.

Banishing Bare Ankles


Old habits die hard, but if your ankles are still on constant display, this is your last chance to get them covered. Bare ankles were one of the overarching trends of the 2010s, but a year into the 2020s they’re beginning to look more than a little dated.

If you must brandish the lower portions of your legs while wearing trousers, we’d advise limiting it to the summer months. Nothing looks more out of place than a pair of exposed ankles peeping out from under the cuffs of a pair of jeans on a frosty winter’s day. There are some really nice socks out there. Why not treat yourself to a pair?

All White

Brunello Cucinelli

One of this summer’s biggest men’s fashion trends is a tricky one to pull off. Get it right and you’re king of the Riviera; get it wrong and you’re Andy Murray on match day.

Despite the risks, going all white is one of the best men’s style moves you can make. It’s also a sure-fire way to keep cool in the heat. Try pairing a crisp white T-shirt with matching chino shorts and a pair of tonal leather sneakers. If it’s all looking too much, throw a navy overshirt on top to tone it down.

Autumn/Winter 2021

Oversized Outerwear


Tailoring isn’t the only thing getting looser in 2021. As we transition into winter, slouchy overcoats, boxy puffer jackets and lengthy parkas will continue to be popular. Oversized belted overcoats in particular are worth paying special attention to.

There’s a lot to be said for this trend as it bolsters one of the best things about winter menswear: the ability to layer. Oversized outerwear leaves lots of room to get creative with your pieces underneath, creating plenty of depth with varying textures and tones. That makes it a winner in our book.

WFH Cosiness

Hamilton & Hare

It’s impossible to say where we’ll be 10 months from now but chances are there’ll still be fluctuating coronavirus restrictions around the world. For that reason, luxe loungewear and house shoes are likely to be trending hard.

Think socks & ‘stocks, hoodies, slouchy overshirts, drawstring pants and loose-fitting tees. The kind of clothing that borders on pyjama levels of comfort but that won’t get you sacked if you have to attend an impromptu Zoom call with your boss.



The revival of fleece is symptomatic of the broader trend in menswear towards outdoors-inspired garb. Thick-pile retro fleeces have been popular as standalone outerwear for several seasons now, while designers continue to work more and more of the fabric into their autumn/winter collections.

This trend is best served in small portions. Keep it to one fleece garment per outfit to avoid going full sheep and mix and match it with other textured fabrics to add another tactile dimension to your cold-weather looks.



Due to its good looks, ruggedness and timeless appeal, leather will continue to be a trend winter after winter. A quality bomber jacket made from the stuff will probably be one of the soundest style investments you’re ever likely to make. It won’t come cheap, but it will last a lifetime. If you haven’t already added one to your collection, this coming winter is the time to do it. And if you really want to stay on trend, why not go for a model with a belted waist?

Textured Tailoring


Ditch the smooth fabrics once the cold weather sets in and watch your tailored looks take off. Materials like tweed, wool, corduroy and twill can help take your sartorial chops to the next level, while adding character and creating focal points within any given outfit.

Keep in mind that it will never look as smart as classic tailoring, so save it for parties, dates and weddings (should the world be back to normal by then) as opposed to anything explicitly formal.

Technical Jackets


The rise of technical outerwear in the fashion world has been one of the overarching trends of the last few seasons and will continue well into the new year. This time around it’s cropped, zip-up silhouettes taking centre stage – easy for throwing on to nip to the shops or for using as a middle layer underneath your winter coat for added ballast and protection against the elements.

Global names in the world of outerwear like Canada Goose, Woolrich and The North Face will continue to be a solid investment, but also look out for smaller names like Crescent Down Works and Adsum, as well as fully-fledged outdoor brands like Arc’teryx.

Relaxed Legs

Brunello Cucinelli

Skinny legwear is off the menu and even slim-fits are dwindling. In their place, we’re witnessing a return to the relaxed-fit pants of the 1980s and 1990s.

Many of us have been pouring ourselves into tight-fitting jeans now for the best part of a decade, and old habits die hard. However, if you embrace a looser leg you might be surprised how much you like it. Not just from a style standpoint, but in terms of comfort too.

Commando-Soled Chelsea Boots

Crockett & Jones Chelsea 11 Boot

The Chelsea boot has always been one of the most elegant, sleek and low-profile boot options around. While that’s all well and good in fair weather, as soon as we’re met with a bit of ice and heavy rainfall they cease to be practical.

Enter: the commando-soled Chelsea boot. Thick, rugged soles have been cropping up all over men’s footwear but nowhere do they make more sense than here. Finally, this classic silhouette is fully equipped to deal with the cold. Not to mention the added chunkiness opens up your wardrobe options – allowing you to play with looser fits and heavy layering.


Atelier Munro

Whether it was oversized suiting or wide-leg trousers, pinstripes were everywhere at the menswear shows. It’s a welcome return for one of the coolest patterns in tailoring. If business casual is well, too casual, opt for fine quality pinstriped suit.

Single breasted is a classic option but why not go all-out 1980s stockbroker and try a double-breasted jacket with peak lapels? That’s right, tailoring has now gone full circle.


Checks are always trending in some way, shape or form. But for the colder months of 2021 it’s Black Watch tartan, buffalo and windowpane that are the ones to watch.

There are countless ways to work these patterns into your daily wardrobe, but one of the simplest is in the medium of a flannel shirt.

Pockets Aplenty

Brunello Cucinelli

It doesn’t seem like long ago that cargo trousers were the absolute pinnacle of uncool. The more pockets a pair of pants had, the less trendy they became. Yet this year that couldn’t be further from the truth.

Pockets are seeing a monumental return to form. Purveyors of premium casualwear like Brunello Cucinelli and Barena have made cargos cool again and to be honest, we’re really enjoying the extra storage. Look out for multi-pocketed outerwear from some of the biggest names in the game, too. Pockets are back, and this time they’re here to stay.

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