Here’s a fun game to try at home. First, grab yourself some paper and jot down all the most categorically uncool items of clothing from when you were growing up. Next, simply tick them off one by one as they inexplicably worm their way into mainstream fashion.

Today, unhip is the new hip – something which (aside from being the reason we can now legitimately use the word “hip”) is having a dramatic effect on how men dress. The movement has been called anti-fashion, a middle finger to previously dominant ideas of what’s stylish. Nerdy staples like baggy fleece jackets, corduroy trousers and touristy trainers are suddenly the toast of menswear.

But why? Simon Chilvers, men’s style director at MatchesFashion, has a few ideas.

“I think a lot of these nerdy elements are a response to all that sleek sportswear and branded product that has been exhausted by Instagram likes,” he explains. “The conversation around dad sneakers has gone mass, to the point of being borderline over. Meanwhile, things like bum-bags have been a slower burn. What I’m excited to see is what comes next in this narrative. Square-toed shoes anyone?”

Functional Fashion Is King

While square-toed shoes aren’t quite there yet, they certainly aren’t out of the question – Balenciaga’s latest derbies are as square as can be. The way things are going, don’t bet against boot-cut jeans making a comeback as designers and shoppers redefine what’s cool.

“Consumers are being more inventive with their looks and we’re seeing shoppers mix up their style and push the boundaries of traditional dress codes,” says Carl Tallents, head of brand at high end retail chain Flannels. “This might come in the form of a fleece being layered under a formal structured coat, or a belt bag worn over a double-breasted jacket.”

The Idle ManThe Idle Man

Practicality is suddenly desirable. “The belt bag, for example, is a classic hands-free style,” adds Tallents. “And, with the likes of Gucci and Fendi creating chic, premium versions, it’s something that can now be worn on any occasion.”

It’s something Olie Arnold, Mr Porter style director has noticed too. “Styles which we used to categorise as being typically “uncool”, we’re now seeing reinterpreted within ready-to-wear collections, he explains. “Unlikely fabrications, such as fleece and corduroy, utilitarian accessories have been given a new lease of life, and as streetwear brands continue to spotlight functional and outdoors-inspired pieces, this looks set to continue.”

Uncool Items That Are Now Cool

Bum Bags

ObeyObey

Bum bag. Fanny pack. Whatever you want to call it, there’s no getting away from the fact that even the very name of this dorky staple just radiates uncoolness. Fittingly, waist-level luggage has long been the domain of embarrassing parents, elderly tourists and other distinctly unfashionable types. That is until the explosion of small bags in men’s fashion catapulted it straight to the top of the hot list.

It was the emergence of the cross-body bag that really got the ball rolling. This streetwear favourite is essentially a bum bag worn diagonally across the body, as opposed to on the hips and has been reimagined by brands ranging from Palace to Prada.

Now, however, pint-size pouches have migrated south to the beltline and are once again being worn in their intended manner (though notice how most brands call them hip packs, belt bags or waist bags). To pull the style off, make sure to wear it as part of a streetwear-inspired look. Try wearing one over a slouchy hoodie and topping it off with cuffed cargo trousers and a pair of nineties throwback sneakers.

Key Pieces

The Best Bum Bags For Men

adidas PARKHOOD WAIST BAG - click to buyherschel Nineteen Hip Pack - click to buyzara BLUE BELT BAG - click to buyeastpak BANE CORE COLORS Bum bag - click to buy

Anoraks

Urban OutfittersUrban Outfitters

Up until relatively recently, it’s always been a pretty reliable rule of thumb to work on the principle that anything with a quarter zip is categorically not cool. These days, however, that’s far from reliable.

Anoraks are the latest in a series of garments – fleece included – to have hiked their way out of the campsite and onto the fashion-week front row. It goes back to fashion’s new fondness for practicality. Stylish technical outerwear brands such as Nike ACG and Veilance are making raincoats cool again. So much so that Gore-Tex is fast becoming the material of the moment in fashion circles.

Staying dry isn’t the only benefit because styling an anorak couldn’t be easier either. Opt for slim-fit denim and suede trainers for a failsafe weekend look – make the footwear a pair of Adidas Gazelles for added terrace fashion kudos.

Key Pieces

The best anoraks for men

NIKE ACG ANORAK - click to buyH&M anorak - click to buyJ.CREW Two-Tone Brushed-Cotton Anorak - click to buyADIDAS PUFFY ANORAK - click to buy

Fleece

Urban OutfittersUrban Outfitters

If you wait long enough for something to come into fashion, eventually it will. And, believe it or not, that includes birdwatchers.

Fleece has long been the fabric of choice for sitting in bushes and looking at avian creatures through binoculars. This has, in the past, marked it as something to be avoided by anyone with even a modicum of sartorial cognizance. However, with streetwear brands increasingly looking to the outdoors for inspiration, fleecy outerwear has made a surprise comeback, and now you’re just as likely to find it being worn by skaters at London’s Southbank as by a 61-year-old retiree called Mark, eating a cream scone at a cafe in the Cotswolds after a long day of looking at crested warblers.

If you’re in the market for a fleece yourself, look out for colourful detailing and retro styling from some of the more fashion friendly outdoors labels. Think Patagonia or The North Face, both of which have recently released plenty of throwback fleecy goodness.

Key Pieces

The best fleece jackets for men

PATAGONIA WOOLYESTER PULLOVER FLEECE - click to buyALBAM Fleece Zip-Up Sweatshirt - click to buyOnly & Sons white hooded fleece - click to buyTHE NORTH FACE Denali Panelled Fleece And Shell Jacket - click to buy

Chunky Trainers

BershkaBershka

Bulky kicks are a trend so colossal that over the past few years they’ve pulled the entire fashion universe into their orbit. And while many cite the Balenciaga Triple S as the shoe that brought your dad’s old sneakers into the style spotlight, it’s nothing that Raf Simons hadn’t been doing with the Adidas Ozweego since 2013.

The Belgian tastemaker pioneered the ‘ugly fashion sneaker’ idea, it was just going to take the rest of the world a few years to catch up. And catch up we did. Chunky trainers have gone from being something you’d only buy for an elderly relative with creaking joints to being a common sight on the feet of teenagers, creatives and celebrities.

Maximalist sneakers may have eclipsed their minimalist trainer counterparts, but styling them effectively requires a little more consideration. The cut of your trousers is the most important thing to consider. Skinny fits are off the menu and should be replaced instead by something with a wider leg opening and a slightly cropped fit. It’s also worth keeping things toned down – when your footwear is this big and loud it doesn’t need to be fighting anything else for attention.

Key Pieces

The best chunky sneakers for men

BALENCIAGA Triple S Mesh - click to buypuma THUNDER SPECTRA - click to buyFila Disruptor II - click to buyzara MAXI SOLE sneakers - click to buy

Corduroy

J.CrewJ.Crew

In a shock turn of events in 2018, corduroy leapt out of the old-folks’ home and onto the runway. As a result, we’ve seen everything from tailoring to trainers reimagined in this unlikeliest of materials, opening the traditionally uncool fabric up to a new and much younger audience.

Now corduroy is for everyone, not just your old high-school geography teacher, grumpy socialists or the kind of character Jeff Goldblum played in the nineties.

But we digress. The point is anyone can get in on the action now. Look out for everyday staples like light jackets, shirts and slim-fit trousers and use them to add a touch of texture to your wardrobe. The key to nailing it is to ensure you only ever wear one corduroy piece per outfit. Overdo it and you could find yourself trying to explain the hydrological cycle to a classroom of bored teenagers. They’d probably like your ‘fit though.

Key Pieces

The best corduroy for men

zara CONTRASTING CORDUROY JACKET - click to buyarket corduroy shirt - click to buyJ.CREW Corduroy Trousers - click to buySELECTED HOMME Cream Corduroy Trousers - click to buy

Dad Jeans

ASOSASOS

With previously uncool items such as bumbags and ugly sneakers now high up on the fashion hotlist, dads all over the world are fast running out of ways to embarrass their children when picking them up from school. And if they thought those ill-fitting, mid-wash jeans were the answer, they’re sorely mistaken.

Loose-cut, straight-leg jeans have long been something of a menswear faux pas, but with Vetements, Off-White and the like now including them in their ready-to-wear collections, and brands like Topman or Arket following suit on the high street, dad jeans’ time to shine has finally come.

You’ll be relieved to know that wearing a pair doesn’t have to mean dressing up like one of Demna Gvasalia’s runway models, nor does it require you to tuck a plain white tee in and start painting skirting boards on a Saturday afternoon. To pull this style of legwear off, wear it as part of a workwear-inspired look. Think sturdy boots, a flannel shirt and perhaps a chore coat, should the weather call for it.

Key Pieces

river island Light blue straight leg jeans - click to buytopman Mid Wash Original Jeans - click to buyEDWIN ED-55 REGULAR TAPERED JEANS - click to buyarket regular jeans - click to buy

Backpacks

Massimo DuttiMassimo Dutti

Just a few short years ago, the idea of teaming a backpack up with tailoring would’ve been unthinkable. Go back a couple of years further still and wearing one at all would have been out of the question if you wanted your style credentials to remain intact.

A backpack was always about as nerdy an accessory as it was possible to get. Somewhere to stash your packed lunch, comic books and trainspotting notes. Now, however, there’s a new climate. This typically uncool piece of luggage has been reinvented, using premium materials and sleek styling to elevate its place within the fashion landscape. Today, you’d be hard pressed to find a high-end label that doesn’t have some sort of luxurious leather backpack in its luggage roster, making it cool beyond question.

If you are going to wear one with a suit, make sure it’s black leather for best results (the backpack, not the suit) and opt for a style free from excessive details.

Key Pieces

The best backpacks for men

ted baker EEEP Webbing backpack - click to buycos LEATHER BACKPACK - click to buyreiss BRONNMAN LEATHER TRIM BACKPACK - click to buyzara BASIC BACKPACK - click to buy