You Can Wear Comfortable Clothes and Still Look Stylish — Here’s Your Proof

More often that not, “comfortable” is regarded as a dirty word in fashion — menswear is inspired by stiff military dress, after all, and some men still haven’t gotten over the horrors that casual Fridays wrought in the ’90s. But casual clothing has come a long way, and style and comfort are no longer mutually exclusive terms. Some of it is even downright luxurious. Take a close look here and you’ll see what we mean.

Top Heavy

01-Top-Heavy

Winter is the time to play with proportion, so why not go all out with an oversized sweater and an equally oversized scarf. The combo will make you feel like you never got out of bed — all the better when you’re waking up when it’s still pitch black out.

Cashmere sweater (price upon request) by Chanel; nylon-wool blend scarf ($75) by Nautica

Room to Move

02-Room-to-Move

Slim cut pants aren’t going anywhere — don’t worry! — but you have a little more room to breathe if you happen to require it. Wide trousers lend themselves well to weightier fabrics that have texture and pattern, perfect for keeping warm and lending some character to an outfit.

Rayon jacket (price upon request) by 3.1 Philip Lim; wool shirt ($180) by Strellson; wool pants ($770) by Deveaux; leather shoes ($1,150) by Louis Vuitton

Soften Up

03-Soften-Up

Soft in the shoulder and to the touch, this roomy coat is big on purpose. It may be unlined, but the generous cut means you can layer underneath to your heart’s content for added warmth — a chunky cable knit sweater is the right place to start.

Wool coat (starting at $3,195) by Boglioli; cashmere sweater ($3,400) by Kiton; cotton pants ($150) by Tommy Hilfiger

Grab and Go

04-Grab-and-Go

The bag that epitomizes this casual approach to dressing is the roomy, never rigid weekender. There’s plenty of space for your oversized pieces, or just throw in a few essentials for a quick night away.

Top to Bottom: Monogram canvas bag ($2,860) by Louis Vuitton; leather bag ($2,860) by Salvatore Ferragamo, at Harry Rosen; leather bag ($800) by Coach