Men's Style Inspiration  / Winter Style  / Cozy Clothes for Holiday Lounging

Cozy Clothes for Holiday Lounging

Basics and layers in all kinds of comfortable fabrics.

holiday lounging outfit ideas
Find your new favorite must-haves with personal styling.

Maybe you’re traveling, maybe you’re staying home for the holidays—either way, there’s a good chance you’re in for some much needed downtime. That’s where we come in. We asked one of our Chicago stylists, Aubrey, for some advice on keeping comfy without compromising on style. Here are five essentials she recommends.

Cozy winter Sweaters


“Knit cardigans are a great way to dress up a dressed-down outfit,” Aubrey says. Layer one over a henley or thermal with a slim pair of joggers. It’s an easy way to avoid feeling too casual when you’re spending time with extended family over the holidays. Pullovers are always a classic option, too.


“Thermals are a must-have in your cozy winter wardrobe,” Aubrey says. “Not only will they keep you warm, but they allow for some breathability, depending on how many layers you put over top.” Better yet, henleys look great on their own with jeans or chinos once you finally do decide to leave the house.

Cozy Henleys


Because who can really relax in jeans? Now’s the time to stock up on joggers. They’re perfect for lounging around the house, and drawstring waists are a bit more forgiving if holiday desserts are your weakness. The tapered, cuffed leg is easy to tuck into a pair of boots, which are much needed to withstand the chill during a quick coffee run.


Don’t forget the footwear. Socks are your first line of defense between your feet and a drafty floor. (Or the puddles that people invariably track in from the snow.) They can also add a touch of style to your look. “If you typically wear solids, try incorporating pattern into your winter socks to add depth to your outfit without reaching too far out of your comfort zone,” Aubrey says. 

Cozy winter Socks


Slippers are necessary when socks just don’t cut it. But they’re also ideal for grabbing the morning paper or restocking the beer fridge in the garage. For ultimate comfort, wrap your feet in layers of toasty wool and shearling.

Knit hats

If it feels like every cool guy you see is wearing a beanie or knit hat during the winter, it’s because they are. They hide untameable bed head, keep you warm, and add something extra to your standard jeans-and-a-shirt outfit.

Aubrey's care tip:

Store your cashmere and wool beanies flat so they keep their shape.

Knit hats
Find your new favorite must-haves with personal styling.