STYLE AND CULTURE

SUNDAY BEST: YOUR MONTHLY STYLE ROUNDUP

By Flo Bellinger, 28 September 2025

Welcome back to Sunday Best: your monthly roundup of the best IRL street style. The layers are back in full force, and our latest adornment of choice has come in the form of plaid. From tartan shirts to checkered blazers, this month’s wardrobe is hardly short on print – and whether you’re leaning into a preppy uniform or just spicing up your capsule pieces, it’s a look that works for everyone. Our ASOS community has been cashing in their checks, and the style is paying off. Keep scrolling for three ways to make this trend your own. P.S. If monthly inspo isn’t enough for you, head to our socials for a weekly dose.

#1: TOTALLY TONAL

Man wearing checkered shirt and grey jeans | ASOS Style Feed

Instagram: @imjamesallen

If you’re looking for a subtle way to inject some print into your 'fit, @imjamesallen has some tips. In this case, it’s all about drenching yourself in one colour – like this slate grey – to balance the visual interest of the shirt. Cool tones are perfect as the temperature starts to drop, and the washed finish on these trousers keeps everything comfortably casual.

GET THE LOOK:

ARKET cotton rich seersucker relaxed overshirt in black and white check, £97
(Similar): ASOS DESIGN super baggy jeans in grey wash, £30
(Similar): Timberland premium 6 inch boots in wheat tan nubuck, £190

#2: SMART-CASUAL

Man wearing beige tailored trousers and check shirt | ASOS Style Feed

Instagram: @ahmedbaddrr7

Talking of casual, @ahmedbaddrr7 knows his way around a tailored trouser and shirt combo. This ensemble would feel more ‘working hours’ than ‘cocktail hour’ if it weren’t for the addition of a baseball cap – a truly unsung accessory that takes your smartest uniform down a notch. The wide cut of the trousers also creates laid-back movement without losing structure, and the heavyweight shirt brings this firmly into transitional territory.

GET THE LOOK:

ASOS DESIGN smart wide leg trousers with double pleats in stone, £32
(Similar): ASOS DESIGN slim fit check shirt in black, £25
(Similar): New Era NY Yankees 9forty cap in black, £23
(Similar): ASOS DESIGN penny loafers in black patent, £42

#3: ALL IN THE JACKET

Man wearing check blazer and jeans | ASOS Style Feed

Instagram: @andrea.asos

For the more adventurous among us, a patterned outer layer can be the most exciting thing about cooler weather. Opting for statement layers is a sure-fire way to mix up a capsule roster – giving your basics new life without needing to invest in an entirely new wardrobe. @andrea.asos checked shows us how it’s done, throwing a wool blazer over a classic white Henley tee and jeans. With the unbeatable socks and loafer combo to finish things off, this winter outfit is really warming things up.

GET THE LOOK:

ARKET cord cap in burgundy red, £35
(Similar): Levi's 555 relaxed straight fit jeans in light vintage wash, £70
(Similar): ASOS DESIGN oversized boxy long sleeve t-shirt, £24
(Similar): ASOS DESIGN slouchy oversized suit jacket in brown check, £80