7 ‘Uncool’ Menswear Pieces That Are Back On Trend For 2024

Image Credit: Artknit Studios

While the world of menswear is constantly changing, there are many garments that are permanently cemented in the style cannon. Think selvedge denim, Breton stripes, Harrington jackets, penny loafers… pieces that will always be cool. There are plenty more that are transitory though, and have seemingly come out of nowhere from relative obscurity. 

These items are often cyclical and trend-led – one minute you wouldn’t be seen dead in them, the next they’re everywhere. They tend to be a bit more out there in design, but offer a functional element that fits a specific need. Think fleece jackets, which were hideously uncool for years; their bobbled fabrics first designed to keep hikers insulated and now beloved for their unique texture and soft feel. 

There are many other examples too, from trail runners to hiking shoes, plastic watches to short-sleeve shirts. So, whether you’re looking to inject life into a staid wardrobe or simply get ahead of the crowd, here are seven uncool pieces that are officially back on trend. 

Sweater Vest 

A public school favourite, the sweater vest is experiencing an unlikely resurgence. And you don’t need a trust fund to rock this trending knit in 2023.

Style heroes ranging from Tyler the Creator to Ryan Gosling have been seen wearing them over the past 12 months, giving the sweater vest a mainstream appeal it could only have previously dreamt of.

The trick to pulling it off is to tap into its eccentric flair. There’s no shying away from the fact you’re wearing a sleeveless jumper, so why not make it the centre piece of your look? Opt for a colourful version complete with a geometric print or abstract pattern and lean into the playful, vintage feel.

Try combining it with pale wash jeans, white socks and penny loafers for a modern-day take on Ivy League style, or finish with sneakers for a more relaxed look. 

V-Neck T-shirt

The V-neck T-shirt has long been the unworthy cousin of the noble crew neck. And for good reason. Throughout the 2000s V-necks would often come in the form of the deep V, with low, navel grazing necklines that revealed far more skin than is ever necessary.

It goes without saying that these styles should still be avoided. It doesn’t matter how much you bench, they will never be flattering.

However, where V-necks can work is with shallow necklines; subtle, high cut Vs that only dip down ever so slightly past the collar bone. Framing your face nicely while hinting that you work out, treat this tee as you would a V-neck jumper and combine with dark selvedge denim and brown leather boots for a simple, masculine look.

Long Sleeve Tee

The long-sleeve tee is a bit of a strange design. It’s an in-between piece: not quite as warm-weather-appropriate as a regular tee, yet not quite as heavy as the more robust sweatshirt or crew neck sweater.

As such, it’s never found its place within the contemporary menswear wardrobe. Until now, that is. Once favoured by the grunge and skate subcultures in the 1990s, when they were layered underneath flannel shirts and tees, the long-sleeve top is having a bit of a resurgence, with brands recognising its potential as a standalone piece.

The trick here is to keep the fit boxy. Go for one in a relaxed cut and wear it over tapered trousers and chunky sneakers, finishing with a five-panel cap for a subtle reference to its skating heritage. 

Fleece Jacket

The aforementioned fleece jackets are so ubiquitous now that it’s hard to remember a time when they weren’t deemed cool.

But they’ve only recently cemented themselves in menswear circles over the last couple of years. That’s not long when you consider they first started cropping up in the late 1970s and early 1980s and for many years were only been favoured by those who actually used them for their intended purpose: hiking.

Fleece fabric was originally developed as a lightweight, breathable yet warm alternative to wool, and has been used for outdoor garments ever since, with the likes of Patagonia making its name off its own version of the distinctive fibre. 

When it comes to styling a fleece jacket today, look to team it with preppy and outdoorsy staples – think cord trousers, rugby shirts, OCBDs, twill pants, flannel shirts and the like.

Hiking Shoes

Staying in the great outdoors, hiking shoes have stepped into the limelight recently. Part of the wider outdoors trend, hiking boots and, by extension, trail runners have become some of the most popular shoe styles of all.

The appeal lies in their practicality and comfort; they were originally designed for long, demanding walks after all, meaning support and cushioning was of utmost importance.

But hiking boots are surprisingly versatile too. Find a pair in brown or black leather and you can wear them in much the same way as your leather work boots. That is with dark or light denim, chinos or tailored trousers, as well as tees, polos and knitwear. 

Plastic Watches 


Plastic watches were once deemed wildly inferior to metal ones. Considered disposable and throwaway, they were the kids’ toys of the watch world.

While some of those claims are actually true, plastic watches are everywhere today – revered for their no-fuss, durable cases and often ingenious designs.

They’re also far cooler today than they’ve ever been, with designs like the Swatch x Omega MoonSwatch giving plastic watches new credibility, while Casio and G-Shock continue to produce classic timepieces that boast just as much heritage as many Swiss watchmakers (without the price tag). 

Short-Sleeve Shirts 

For a long time they were thought of as inferior to long-sleeved versions, but short-sleeve shirts are now arguably cooler in every conceivable way.

There are still some pitfalls that are to be avoided if you want to pull them off though. The first is with the collar, which generally works best when it’s a Cuban design. This more relaxed, open-neck style better suits the informal nature of the short-sleeve shirt, firmly cementing it as an easy, effortless spring or summer option.

The next thing to look out for is the fabric. Again, you should prioritise relaxed materials like cotton, terry cloth or linen to further distance the shirt from stuffy formalwear.

Charlie Thomas

Charlie Thomas is a writer and photographer, contributing to publications including The Independent, The Times, The Rake and Black + White Photography magazine. His photography has been exhibited by Photofusion, Central Saint Martins and Photo Co-Op.