Respect is something you earn. At least, that’s what happens in menswear. The Gandys and Cheshires of the world deserve praise for their well-selected looks – outfits helped by the sort of salary that can afford Savile Row suits and personal stylists.

But money doesn’t always buy taste. And today’s street style gods haven’t always lived on Mount Olympus. Many suffered through questionable phases but, after wardrobe penance, their sins were forgiven. Yes, the road to style salvation may be a jungle, but it seems a leopard can change its spots. Or stripes, if the new season demands.

David Beckham – Tosh ‘n’ Becks

Nobody can question David Beckham’s style status. As the face of everything from H&M collabs to Emporio Armani underwear, the former England captain transitioned from football to fashion in the shake of a lambswool jacket.

But before he hung up his boots, Number 7 made some serious style missteps. The Beckham we know (and love) was responsible for his-and-hers biker leathers, problematic cornrows and enough wet look gel to style an N*Sync tribute band.

True, the man has made many a bold move that commands respect. However, risks don’t always reap rewards – case in point, that sarong.


David Beckham - Style/Fashion Mistakes


David Beckham - Style/Fashion Icon Outfits

Tom Hardy – Hard Knock Life

Long before Tom Hardy mastered the red carpet tux, he was just a young, Alice band-wearing model looking for his big break on The Big Breakfast. Yes, you read that correctly.

It seems Hardy had a bit of a love affair with tight tank tops and cargo pants. We can’t confirm whether The Revenant star ever auditioned for Take That, but it certainly looks suspicious.

And it only gets worse. Such style sins will forever be shadowed by the resurgence of Hardy’s MySpace. The fossil of social media is a wardrobe skeleton for anyone unfortunate enough to forget their old password; Hardy’s trucker cap, tribal tattoos and up-and-over selfies should go the same way as his 2012 romcom This Means War. Some things are better forgotten.


Tom Hardy - Style/Fashion Mistakes


Tom Hardy - Style/Fashion Icon Outfits

Gary Barlow – Take That (Well Away From Me)

Speaking of Take That, Gary Barlow rebuilt himself in more ways than one. As if relaunching a successful music career wasn’t enough, the ‘Patience’ crooner became an unlikely menswear hero with sharp plaid three-pieces and the definition of designer stubble.

Seems like we’ve all suffered a bout of amnesia, though. Back in the day, Barlow was better known for his peroxide bleached locks, which he accessorised with thrusting, topless close-ups and posing pouches. Who said record labels don’t exploit young musicians, again?


Gary Barlow - Style/Fashion Mistakes


Gary Barlow - Style/Fashion Icon Outfits

Justin Timberlake – Bringing SexyTack

Smart, handsome, understated – Justin Timberlake has been on the best dressed circuit for some time. But only after he ditched whichever stylist was responsible for a dossier of war crimes:

Exhibit A. The macaroni cheese perm. Learn from JT’s error and don’t pair a complexion the same shade as overcooked noodles with this eyesore of a haircut.

Exhibit B. Rhinestone studded shirt and matching bandana. For the Dolly Parton/Wu-Tang collab that will never, ever happen.

Exhibit C. The Texan tuxedo.

Exhibit D. WTF.

We rest our case, your honour.


Justin Timberlake - Style/Fashion Mistakes


Justin Timeberlake - Style/Fashion Icon Outfits

Kanye West – ‘Ye Or Nay?

Although he’s wailed about being locked out by the fashion monarchy, today Kanye has earned his spot on the throne. Close ties to Balmain, Anna Wintour on speed dial and, most importantly, his own sold-out Yeezy collection have all cemented his sovereignty.

But he hasn’t always worn the crown. Think of the shutter shades or oversized scarves that Gemma from Year 8 Biology loved. Think of the College Dropout era, filled with sad, shapeless jumpers that made Kanye look more UCL professor than Ivy League bad boy. And think of that bizarre trend of layering polos in the early 2000s.

The self-declared genius hasn’t always been so clever.


Kanye West - Style/Fashion Mistakes


Kanye West - Style/Fashion Icon Outfits