Everything To Chuck When Turning 30 (And What To Wear Instead)

Baggy Beanies

At some point circa 2005, beanies went from Usher-tight to oversized. It was a look that David Beckham himself wholeheartedly embraced and, as with most trends Golden Balls gets behind, it blew right up. Soon, any metrosexual worth his Swarovski ear stud and deep V-neck tee was opting for preposterously oversized headwear to top it off.

“A slouchy beanie makes every outfit instantly sloppier,” says Brooke Philips, lead stylist at men’s personal shopping service Thread. And she’s right – now that you’ve hit the big 3-0, there’s no room for this student halls brand of slovenliness.

The Solution

It’s not the beanie itself that’s the problem. It’s the baggy. Much more age-appropriate is headwear that fits. “A snug-fitting cable or ribbed-knit beanie does the same job,” says Philips. “It’s also warmer, more comfortable and looks sharper than something with a lot of flop.”

Alternatively, if you’re worried that wearing a beanie of any kind is going to make it look like you’re en route to rob Macaulay Culkin’s house, opt for a winter-ready leather or wool baseball cap in its place.

Novelty Underwear

Novelty underwear is a rite of passage for most men. When you’re a teenager, it’s the go-to Christmas gift for relatives intent on finding skivvies that’ll give you a chuckle. But we’re still not laughing.

Hopefully by you’ll have had the sense to leave trunks that declare you a ‘Beer Monster’ or baggy boxer shorts emblazoned with the warning ‘In Case Of Emergency, Pull Down’ far, far behind you. At mum and dad’s. Along with those saucy lad’s mag posters.

The Solution

Underwear should cover your buttocks, not make you the butt of jokes. “Plain boxer briefs combine the best of both worlds, they’re suited to most body types and hold everything in place without drawing too much attention,” says Mr Porter style director Olie Arnold.