STYLE AND CULTURE

KID CUDI'S GOT THE KEY TO COOL-GUY TAILORING

By Ayis Stephen-Diver, 11 August 2025

Streetwear and echoes of the Y2K era will always be mainstays in the style zeitgeist, but there’s something refreshing about icons of hypebeast culture showing out in tailoring. Musical polymath Kid Cudi has gone through every (and we mean every) phase of millennialcore, from 2010s club casual to loud logomania – but nothing hits quite like when he swaps graphic tees and hoodies for shirts and trench coats. With his 11th studio album, Free, just around the corner, we’ve rounded up Scott Mescudi’s greatest tailoring moments.

STAY TRENCHED

Kid Cudi wearing a brown trench coat and a black silk set

Picture: Getty

Kid Cudi is used to remixing traditional tailoring to his whims. A longtime lover of Saint Laurent, he swapped the classic tuxedo for a black silken set at the house's AW24 show. The look's undone pyjama-esque vibe was elevated with help from a neutral trench coat, aviators and a cross earring. Use this ‘fit as a reference for any evening escapades that would benefit from a little sophistication.

GET THE LOOK:
Similar: ASOS DESIGN oversized satin shirt in black, £30
Similar: ASOS DESIGN wide leg suit trousers, £35
Similar: ASOS DESIGN trench coat in stone, £70
Similar: Ray-Ban Aviator sunglasses with grey lens, £203

SEASONAL LAYERING

Kid Cudi wearing a black leather jacket with Lola Abecassis Sartore

Picture: Getty

If there’s anything you need to know about Kid Cudi, it’s that he loves a leather layer – and he knows how to style them. He gave us a valuable lesson in cold-weather dressing here. While the oversized leather coat makes a statement on its own, a denim shirt peeking through and some smart-casual basics result in a crisp, city-ready combo with dimension.

RECREATE HIS LOOK:
Similar: ASOS DESIGN faux leather trench coat, £85
Similar: Mango 100% cotton t-shirt in white, £12.99
Similar: ASOS DESIGN smart tapered trousers, £38
Similar: Carhartt WIP denim shirt, £100

PRINTS AND PIZZAZZ

Picture: Getty

If you immediately associate printed shirts with summer, think again – everyone from Timothée Chalamet to Kid Cudi is investing in them to go alongside tailoring right now. While at the Knuckles world premiere earlier this year, Cudi teamed a clean-cut wool overcoat with tapered trousers and a micro-polka-dot shirt. We’re major advocates of taking your monochrome looks the extra mile with textures and prints, and Cudi got the memo. The key to capturing the vibe: unfastening a few buttons and teasing a necklace.

GET THE LOOK:
Similar: Topman print shirt in black, £45
Similar: ASOS DESIGN wool look overcoat, £70
Similar: Weekday oversized tailored trousers, £49
Similar: Lost Souls coin pendant necklace, £16