5 Men’s Fashion Trends To Keep For 2020

With a seemingly never-ending drip of new-ins and new-outs, it can be hard on both your wallet and your wardrobe to continually play catch-up with the latest menswear collections.

Luckily, this season sees some of 2019’s biggest trends spill over into 2020. So as well as breaking down what you should be holding on to in order to nail the key looks, we caught up with some industry insiders to get the styling tips that’ll maximise the wears from last year’s investments.

Loosening Up
Form-hugging fits had been on their way out for a while but 2019 was the year that really finished them off. From baggy denim to Chandler Bing-approved oversized tailoring, loose cuts crept from the fringes of fashion and into mainstream menswear, marking a sartorial shift that looks set to continue long into the next decade.

It was a breath of fresh air for both our wardrobes and our testicles, as spray-on legwear disappeared almost entirely – replaced instead by straight-leg, relaxed and wide-leg fits – and boxy ’90s-inspired outerwear reigned supreme.

How To Wear It
When you’ve spent the last year pouring yourself into slim- and skinny-fit everything, the idea of wearing something that doesn’t cling desperately to your calves can be a daunting prospect. The key to nailing it lies in knowing how to create a clean, cohesive silhouette from head to toe.

In most areas of menswear, contrast is a good thing, but not here. Wearing a pair of tight-fitting trousers and a baggy jacket for example will look unbalanced and disproportionate. The trick is to pair similar cuts to create a look that flows from head to toe. If your legwear is relaxed, whatever’s on your upper half should be, too.

Commando Soles
For several years, the overarching trend in men’s footwear fashion has been marked by a move away from minimalism and simplicity, and towards OTT styling and bulkiness. The rise of maximalism has been most evident in the sneaker world, but 2019 saw it take hold of our boots and brogues, too.

The commando sole is formal footwear’s answer to chunky sneaker madness. It’s bold and bulky, and has a way of completely altering the overall look of a shoe. Everything from classic Chelsea boots to dressy Derbies received the thick-tread treatment over the course of the last year, and with those rugged soles offering increased traction in wintery conditions, this is one of those rare trends that’s as practical as it is stylish.


How To Wear It
The best way to rock commando soles depends largely on the type of footwear they’re attached to. A commando-soled Chelsea or Derby boot, for example, is best paired with sturdy cold-weather pieces, giving anything too fitted a wide berth. Think regular-fit raw denim, a thick twill overshirt and a chore coat.

The classic Derby shoe is another silhouette that works well with a thicker sole, but the low-top design makes it a little more versatile, meaning it could even be worn with tailoring for less formal occasions. Just steer clear of skinny fits as the chunkiness created by the rugged sole can be a little jarring in contrast.

The Great Outdoors
It’s tricky to say what an era will be remembered for trend-wise without the benefit of hindsight, but if we were going to put money on it, we’d say that 2019 will go down as the year that function went fashion. Pockets were plentiful, the biggest names in fashion were playing with technical fabrics, and your bird-watching uncle’s street cred was at an all-time high.

This wasn’t just any old trend, though, it was one that actually made our lives easier. Because, let’s face it, a Gore-Tex hardshell is always going to hold up better in the rain than a wool peacoat. This considered, we’ll definitely be continuing to wear our outdoor-inspired garb into the new year and we’d suggest you do the same.

How To Wear It
As was evidenced perfectly by the short-lived nu-rave trend of the mid 2000s, it’s never a good idea to deck yourself out head to toe in a trend unless you want your Facebook memories to get really awkward in a couple of years’ time. Instead, pick up a few key pieces and use them to update your current wardrobe. The obvious choices where outdoor gear is concerned would be a technical jacket, a fleece and some mountain-friendly footwear.

Use layering to create depth and keep legwear relaxed for balance. Accessories shouldn’t be neglected either; think thick textured socks, an appropriate timepiece, suitably outdoorsy luggage and a beanie to tie it all together.

Tailoring & Knitwear
Texture and layering are two of the pillars of advanced dressing, and they’re both integral to one of 2019’s hottest tailoring trends. Suiting worn with knitwear was everywhere over the last 12 months, marking another step in the general loosening up of dress codes across the board. Stuffy shirts were replaced with fine-gauge rollnecks, fisherman beanies were teamed up with unstructured blazers and statement crewnecks lent simple suits a fresh lease of life.

It’s more than just a fleeting trend, though. This simple style move looks set to become a staple of modern menswear and is something that exudes the sort of timeless appeal needed to carry it into a new year and beyond.

How To Wear It
The beauty of knitwear and tailoring is that as long as you stick to the right pieces, it’s fairly straightforward to nail. Provided you’re not attempting to pair a Coogi jumper with a tuxedo, on the whole you should be fine.

The hero piece here is the rollneck, particularly one in a fine gauge to enable it to slip comfortably underneath a suit jacket without limiting movement. This knitted favourite makes an excellent substitute for a shirt when a suit needs to be dressed down without straying into sloppy territory. Generally speaking, the darker the colour, the smarter it’s going to look.

Weather-Proof Sneakers
As sun-drenched strolls home from the office mutate into dark, frigid commutes in torrential rain, sneakerheads all over the world are faced with a horrifying choice: to ruin their most prized possessions in the adverse weather or, perhaps even worse, to consider wearing footwear other than sneakers for the next couple of months.

Thankfully, 2019 and its taste for functional fashion brought with it a solution to this age-old seasonal conundrum: Gore-Tex sneakers…and plenty of them. From Nike to New Balance, every trainer brand worth its salt was experimenting with the waterproof fabric this year and we still can’t get enough of it.


How To Wear It
The selection of Gore-Tex sneakers hitting shelves over the course of the last year has included everything from waterproof versions of old classics like the Air Force 1, right through to high-performance trail shoes from the likes of Salomon and Hoka One One. This considered, how to style them depends heavily on the type of sneaker you opt to buy.

For all-round versatility, the best course of action is usually to go for something low-key. Timeless sneaker designs like the Stan Smith, the Superstar and the Converse All Star have all had Gore-Tex makeovers in 2019 and look just as good across your entire wardrobe as they always have. For more technical styles, match with outdoorsy pieces like cargos, down jackets and hardshells.

1Wearable Luggage: The Best Chest Rigs And Holsters To Buy In 2020Wearable Luggage: The Best Chest Rigs And Holsters To Buy In 2020
21920s Men’s Fashion: The Complete Guide1920s Men’s Fashion: The Complete Guide
312 Cool Hairstyles For Men That Have Stood The Test Of Time12 Cool Hairstyles For Men That Have Stood The Test Of Time

White Tie Dress Code For Men: What It Is And How To Wear It White Tie Dress Code For Men: What It Is And How To Wear It
Read on, your lordship
A Beginner’s Guide To Watch Complications A Beginner’s Guide To Watch Complications
What you should be on the lookout for when purchasing a luxury timepiece
Alex Turner’s Best Hairstyles: 6 Ways To Look Like A Rock Star Alex Turner’s Best Hairstyles: 6 Ways To Look Like A Rock Star
From rockabilly quiff to a shaved head, he’s done it all
The Best Winter Boots For Men 2020
The Best Winter Boots For Men 2020
Don’t step a foot outside without these
Cold feet are a fact of winter, as reliable as dark mornings and drunken Decembers. The shoes you wear the rest of the year round – perforated trainers that let the chill in and low-rise shoes that let the rain in – don’t cut it in the worst of the weather. You need some winter boots and not just one pair, preferably two or three.

This is footwear originally designed for timber yards, hiking trails and the trenches of war; so you can be confident it will get you through a slightly frosty commute. In style, too, because the best winter boots are as good looking as they are practical.

Fashion has a thing for technical clothing of all kinds right now (hiking style and workwear are trends that won’t quit), but it’s always been happy to appropriate boots – from soldiers, mountaineers, riders and blue-collar workers. Those boots have the attributes all boots should have: durability, practicality, comfort and weatherproofing.

And despite those chunky soles and unforgiving leathers, winter boots are some of the most versatile shoes you can buy. Invest in the right pair and they’ll last decades if you look after them as much as they do you. So, best foot forward. Find the style that suits you best below, along with the go-to ways of wearing them.


What To Look For In Winter Boots
Quality Materials
Good winter boots shouldn’t be dirt cheap if you want them to last, and you should. “The quickest way to spot quality in a boot is by the quality of the upper material,” says Tim Little, creative director and CEO of Grenson.

“A well-made boot will always be made of quality leather because no one would go to the effort of making a great boot in cheap leather. Quality leather always has soft creases and usually is hand polished so you can see the patina and dark and light patches. It isn’t always uniform.”

Alternatively, look for tanned leather, which tends to be thicker than painted leather and shouldn’t need as much weatherproofing.

Goodyear-Welted Soles
A solid footing in the winter means a pair of boots that feature the famous Goodyear welting technique to stitch the sole firmly to the upper via a rib-like strip of leather or canvas.

“The stitching of the welt can be seen above the welt and the sole stitch (through the welt) underneath the sole,” says James Fox, brand director for Crockett & Jones. “Be careful though. If you cannot see the continuation of this stitch through the sole you could be looking at a pair of cheaper, cemented boots using an imitation welt.”

“A well-made boots brand has detailed information about how they make boots, where they are made and what materials they use,” says Rik Van Dijk from Red Wing. “A good boot maker is proud of this information.”

“And if you are looking for a winter boot with the perfect fit and quality? Go to the store of the boot maker or a speciality store. There you get all the information and fit you need to get the perfect boots for your feet.”

Recognising that most of us only wear our boots to either the office or the pub, shoemakers have, in recent years, fitted their designs with comfortable and practical soles. Combat-style treads will make you even more sure-footed while contrast white rubber soles offer some smart-casual hybrid styling.

Likewise, shoemakers (even the likes of Dr Martens) have made efforts to offer lighter versions of their chunkiest and most iconic styles with new materials offering the same wear and practicality.

Red Wing
Red Wing

The Best Winter Boots Styles
Hiking Boots
Have you been spending your weekends training for a forthcoming trip up Kilimanjaro? If the answer’s no, then you can be forgiven for overlooking the humble hiking boot as a viable footwear option. But only just.

Regardless of your outdoorsy aspirations (or lack thereof), hardy hiking boots have established themselves as foul-weather footwear essentials over the past few years – especially among sharp men who prize a shoe’s ability to face down all manner of meteorological nasties in style.

We’re not experts in adventure sports, so we’ll leave recommending boots for seriously tough terrain to the professionals. What we can do, though, is suggest designs that are ideal for navigating city streets, heavy dog walking sessions and the occasional trip to a countryside pub.

You need a pair that offers untold levels of comfort, ankle support and other orthopaedic box-ticking features such as full-leather linings and cushioned footbeds. (Although you could sack that off and get a beautiful but hardly practical suede pair from a high-fashion designer that hasn’t seen a mountain in their lives.)

Team them with other tough-as-old-boots menswear staples like raw denim, corduroy, twill or flannel shirts and cable knit jumpers. You could also pair them with rainstoppers and fleece to lean fully into the outdoors trend. Or be bold and use them as a striking counterpoint to tailoring – just not for your next job interview.

How to wear hiking boots

Brogue Boots
If you’re not ready to go full Bear Grylls with a pair of hiking boots, there are other, subtler ways to infuse your winter look with some outdoorsy influences. A sartorial hybrid, the brogue boot comes with the same reassuring weight and solid construction of hiking boots, but with all the wing-tipped, country-manor smartness of brogues.

As a general rule of thumb, you can wear your brogue boots with any outfit you might normally wear with traditional brogues, so lace up a dark brown or black leather pair with heavier wool suiting, and smart trouser and shirt/cardigan combinations.

However, owing to their winter-readiness, brogue boots also play well with pieces that straddle the rugged-refined divide, such as heavy-gauge knitwear, gilets, waxed and quilted jackets, as well as heritage fabrics such as corduroy and tweed.

While sock-flashing isn’t necessarily frowned upon when wearing a pair of these, it’s not an entirely natural fit with the brogue boot’s finesse either. Stick instead with trousers with a neat break (i.e. that finish around the top set of lace eyelets), or roll more casual trousers and jeans up to the same point for a smart finish.

Look out for rubberised soles for some extra winter practicality.

how to wear brogue boots

Work Boots
Some of the best boots ever made were first designed decades ago for people to wear in factories and shipping yards. The steel toe caps may not have survived the fashion crossover, but many other features have: waterproof materials, padded ankles, high-grip soles and cosy linings. Why wouldn’t you want those things for your feet when it’s freezing outside?

The most iconic work boots – the Timberland Yellow Boot, Red Wing’s classic moc toe – have remained almost unchanged for decades, which makes it surprising that they’ve been adopted by such diverse style tribes. Hip-hop artists, lumbersexuals and workwear enthusiasts all love a work boot.

That means you can pair them with a range of casual (always casual) outfits, from joggers to jeans, trucker jackets to parkas. Look for dyed leather or waterproof nubuck and sealed seams to keep the puddles at bay.

Combat-Style Boots
Like most items in a man’s wardrobe, boots have a proud history of military service. From high lace-ups designed to keep out trench foot to modern tactical designs, combat boots have recorded a number of victories on the fashion front.

Right now, they’ve not just won the battles, they’ve won the warcore. The directional trend for combat trousers, holsters and all things military means there’s rarely been a better time to buy this style. Not that you have to leave the house looking like a character from Call of Duty.

Look at Ryan Gosling’s character in Blade Runner 2049. He paired tactical boots you can buy on Amazon with a statement overcoat. Or designer Charlie Caseley-Hayford who wears his trademark high boots with classic tailoring. Streetwear fans might pair them with jeans and a bomber. Or an easy middle-ground is heritage wear: wool, twill cotton, generous fits and plenty of herringbone.

Chelsea Boots
The Swiss Army Knife of your shoe rack, the Chelsea is by far the most versatile boot you can buy; the right pair looks just as good worn with a suit or tailored trousers Monday to Friday as it does a leather jacket and shredded skinny jeans for a gig at the weekend.

While suede Chelsea boots have something undeniably louche about them, it’s a delicate material that is hard to keep pristine in or just after a downpour. If you can’t be bothered with regular cleaning, brushing and applications of protector spray all winter, opt for easy-wipe leather instead. As it happens, a pair in smooth black leather is much closer to the iconic original anyway.

Details to look out for include autumn-ready rubber soles and the classic heel pull, a practical feature that many modern iterations don’t have (but should). Also, mind your toes. Pointed-toe Chelsea boots, when worn with a suit at least, look a little off, so keep your sights firmly set on round-toed styles instead.

how to wear Chelsea boots

Leave a Reply

Your email address will not be published.

My Cart (0 items)

No products in the cart.