Holiday Looks That Are Actually Comfortable

One editor (hi) bought these back in 2021 and hasn’t stopped talking about them since. They hug every curve and land just above your belly button without digging into your waist. The faux leather is soft to the touch and will elevate everything from a casual tee to a long tunic sweater. Add a pair of heeled boots for your next holiday happy hour or low-top sneakers for a more relaxed vibe. ($98, Spanx)

Running low on time to get ready for your event? Enter: this oversized turtleneck sweater. It’s long enough to cover your front and backside, so it’s easy to throw over leggings or jeans and head out the door. It comes in two colors: a festive red and a light gray. You’ll wear this wardrobe staple well beyond holiday season. ($99, Nordstrom) 

As we said, we believe in versatility, which is why we can’t in good conscience recommend a boot that limits our pant options. These wide-calf boots are at the top of our list. They’re wide enough to wear over skinny jeans but narrow enough to wear under loose pants. They have a chic square toe and a block heel that’ll give you a lift, but make walking all day or dancing all night a breeze. ($89.99, DSW) 

There’s no better time than the holidays to bring back your favorite jeans-and-a-cute-top combo. And this holiday season, we’re reaching for this sequin long-sleeve top from Anthropologie. It features pretty gathered shoulders and eye-catching bishop sleeves that add a little extra movement. It comes in four different colors: carbon gray, a beige-toned silver, lavender, and dark green. Wear it tucked into high-waisted pants or skirt for a more tapered look. ($118, Anthropologie) 

Speaking of high-waisted pants, these viral Halara pants show up in our shopping guides time and time again for good reason. They’re super-stretchy and feel more like sweats than they do “real” pants, but their tailored silhouette makes them appropriate for dinner parties and work events. There’s no button or zipper, just an elastic band. They come in regular, petite, or tall lengths, and in sizes XS-3X. ($29.95, Halara)

These H&M booties are kind to both your feet and your wallet. They have chunky treaded soles and a sherpa lining that will keep you warm during outdoor activities. The front zipper makes it easy to take them on and off. Reviews say they run on the small side, so we recommend sizing up. ($59.90, H&M) 

You’ve probably seen the drop-waist dress trend all over your feeds, and currently, we’re obsessed with this $25 one from Target. Its layered ruffled skirt hits right above the knee, and the mock-neck adds an elegant flair. Dress it up with Mary Janes and a metallic bag for your next party or with boots and tights for work the next day. ($25, Target) 

Consider this vegan leather jacket the LBD of casual wear. It has a boxy silhouette, so you can layer it over a sweater without adding bulk, and the cropped length helps add some shape to  looser-fit dresses. It has two pockets on the chest for your valuables and a pointed collared neckline that keeps the look super sleek. ($128, Free People) 

Like the drop-waist dress, Mary Janes are back in a big way. These elegant double-strapped ones from Clarks feature a small chunky heel that feels like a flat but gives you just the right amount of lift. Wear them with your favorite jeans and a sweater for the holidays, then with floaty dresses when the weather warms up again. ($120, Clarks) 

Silk you can throw in the wash? Under $100? We’ll take 20. This knee-length skirt comes in 17 colors and has a sheen that catches the light in the best way. Some HQ’rs have paired theirs with a cropped tee for a casual warm-weather look, but this season, we’re pairing it with a chunky black sweater and our favorite boots. ($60, Quince) 

On the hunt for the perfect knit sweater? Meet this one from Banana Republic. It’s made of a stretchy, ribbed knit with thick cable-knit detailing to give it a chunky look. Its cropped hem hits just above your belly button, so you can show off your high-waisted pants or skirt. This one’s super cozy — and no, we won’t tell anyone if you end up getting more than one. ($44+, Banana Republic Factory)

This summer, cowboy boots graduated from music festival wear to a staple shoe in our closets, and we’re wearing them right through the winter. These cowboy boots have a tall shaft, which makes them a trendy option for pairing with skirts and dresses, and the chunky block heel offers both lift and stability — ideal for schmoozing at a cocktail party. They come in tan and black, but we’re loving the metallic silver for a festive pop. ($69.99, DSW)

Not that anyone asked, but we shoved our jeans to the back of the closet to make room for these convo-sparking pants. Whether you opt for the dark green, black, or champagne color, you can be sure you’re nailing your holiday party’s dress code. Dress them up with a button-down and heels, or keep them casual with a tee and Chelsea boots. ($98, Free People) 

No head-turning pants or IG-worthy skirt is complete without a streamlined black turtleneck to pair them with. This ribbed one from Athleta is lightweight, but you won’t have to worry about it being see-through. It’s machine-washable and can go from activewear to your next company party in no time. ($69, Athleta)  

If you hopped on the kitten heel train this summer, why not upgrade to the 2.5-inch heeled ankle boot train? They’re a little taller than a kitten heel, but not so tall that you’re internally panicking about losing your balance while trying to engage in conversation. (Trust us on this one.) They come in black or brown smooth suede, and soft black leather. Customers have also called out the gold details on the side zipper as a great way to add extra bling. ($180, Sam Edelman)

Sometimes, it all comes down to the accessories. If you’ve already got your holiday outfits locked down, spruce them up with these 18-karat gold earrings. They’re a subtle nod to the viral Bottega teardrops, but with their own sophisticated flair. They’re chunky, luxurious, and perfect for any occasion. ($198, Mejuri) 

Channel your inner Blair Waldorf with this velvet knotted headband from J.Crew. It’s the quickest way to add a touch of elegance to any outfit with virtually zero effort. Customer reviews say it’s light, comfortable, and (more importantly) won’t cause headaches. It’s not too wide, not too narrow, and fits just right. ($16.50, J.Crew) 

Listen, we get it. If all-black is your winter go-to, keep each look fresh and party-ready with this metallic scarf. It’s wide enough to double as a wrap for an evening look, and it comes in eight wintery colors — yes, including black. With an under-$50 price tag, it also makes a great last-minute gift. You’re welcome. ($33.60, Macy’s)