How to Style Loungewear Sets Without Looking Sloppy in Winter 2026

I never used to understand why my matching sweats always ended up looking less chic than I’d imagined. But I now know that learning how to style loungewear sets is what truly brings the whole outfit together—while still ensuring that you’re warm and cosy in your favorite comfy co-ords.

Turns out, intentionally layering your matching set with structured outerwear, chic accessories, and a trendy pair of sneakers is the simple yet effective formula for a laidback look that’s sophisticated, rather than sloppy. So, there’s no reason why you can’t still feel put-together while pottering around town.

Whether you’re dressing up your trusty grey sweats for the school run, or taking your activewear set on an errand run before pilates, there are plenty of ways you can go about making your best loungewear look a little more carefully curated this winter. Ahead, you’ll find inspo for five different outfits.

1. Classic Cuffed Sweats and a Wool Coat

Crewneck sweatshirts and straight-leg trousers may be the preferred option these days, but there will always be something rather iconic about cuffed joggers paired with a classic hoodie. Bonus points if they’re in a light grey wash. For a slightly more polished feel, make like Mila Kunis and style your sweats with a simple yet sophisticated longline wool coat that preferably has a slightly oversized fit. And keep the shoes simple by opting for Sambas or your personal favourite fashion sneakers.

2. Pajamas as Outside Clothes

2025 was definitely the year that wearing pajamas outside of the house became a proper thing. As well as brightly-colored silk or satin sets, pinstripe linen pajamas were some of the most popular picks during the warmer months—and a lightweight trench coat was the favored accessory. During winter, keep the silhouettes similar, but prioritize warmth by opting for a weighty belted wrap coat. Going for more muted pajamas? Embrace color in your shoes and accessories.

3. Statement Monochrome Tracksuit

Wondering how to style loungewear sets that are already making a statement as they are? When you’ve got a bold tracksuit, instinct will likely tell you to steer clear of adding any more of the same color—but I think you should ignore this, and lean into the modern monochrome vibes instead. Think: scarves, beanies, and bags in as close to the same color as possible, and plenty of chic shiny jewelry.

4. Cosy Pilates Princess

Your workout set will likely stay covered until you’re in the studio, but that doesn’t mean you can’t style it up in a way that’ll still have you feeling cute before and after your workout. For a flattering contrast with skin-tight leggings, layer up in a padded puffer or a fluffy cropped jacket, and have a baseball cap or sports headband on hand to stylishly disguise those sweaty roots. Hitting up a pilates class? Great news—that means you can also wear your favorite chunky fashion sneakers.

5. Grungy ’90s Velour Vibes

Babe, the naughties are calling—it’s time to dust off the Juicy Couture tracksuit and pick yourself up some futuristic-looking Y2K sunglasses. If you’ve got a chic velour set, lean even more into the heavy textures by accessorizing with fluffy faux fur jackets and velvet bags. On your feet, you can’t go wrong with a trusty pair of UGG boots.

A version of this article was originally published by Glamour UK.