Shawn Stephens

2025-04-21 09:16 37

When Shawn Stephens enters a room, you know about it.

The long-time Esquire alumni is a PR guru known for his bold and daring sense of style. So we asked the man to provide us with style tips for a laid-back relaxed look (even though he would almost certainly never use them himself).

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Big, ‘Ugly’ Trainers
Find a great casual shoe that is comfortable because nothing kills the ‘athleisure’ look like a pair of dated sneakers. Raf Simons and Balenciaga are bucking the minimalism trend set by brands like Santoni, Common Projects with chunky, outlandish designs in all manner of shapes and colours.

Accessories
Get on the minimalist bandwagon and go for simple, unfussy accessories. Try ‘casual’ accessories like leather totes, aviator sunglasses and a classic watch.

Oversized blazers
All things ‘anti-fit’ are a good way to achieve a laid-back, look. Boxy tailoring isn’t for everyone—especially if you’re short. It’s a much easier look for the taller guys to pull off. If worn incorrectly, it can make you look shapeless and clueless.

Juxtapose aesthetics and use separates 
Try mixing the casuals with more formal aspects of your wardrobe together so one piece excuses the other.
You will definitely be owning your laid-back style more confidently. Avoid casual clichés Baggy sweats and/or hoodies are a no-go. Leave them for lounging around the house. Instead, opt for trousers with an elastic waist and a cuffed hem.

Treat your casual clothes well
Laid back doesn’t mean wrinkled and sloppy!

Mix in active wear
The athleisure movement has seen sporty details such as drawstring waists and cuffed ankles appear on tailored trousers. So sub them in to take the edge off a formal outfit or smarten up one that is too casual.

Sportswear musts
Keep it simple and monochrome, but if you want to add a hint of colour, then one is fine.

Express yo’self
Make sure that your off-duty style is no more than 25 per cent on display. You don’t want to look like a walking advertisement.

Keep it fun
Laid-back doesn’t have to mean dull and boring. Explore new styles, trends on brands and up your casual-style game.