What to Wear for Every Holiday Party

From a casual house party with old pals to a semi-formal company party with coworkers, here’s how to not stick out like a sore stocking.

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Ah, the holiday party: That annual challenge where you’re expected to look nice, but also sort of cosy, while perhaps also somehow incorporating red and green in a way that doesn’t look like absolute festive crap. We asked some experts what to wear to every kind of holiday bash, because this is the season of goodwill and we’re just chock full of the stuff.

The Holiday House Party Look
When raging it up at a holiday house party, personal stylist Meg Gallagher suggests dressing casual and seasonal, rather than overly festive. She recommends wearing a chunky cardigan, a thick (and perhaps festively-colored) button-down shirt, dark-colored jeans and boots. For an even more casual look, “You could swap out the cardigan and the button-down for a plaid shirt jacket and a T-shirt,” Gallagher says. So you’ll look kind of like a lumberjack, but one who only chops down Christmas trees.

If that still feels a little too bougie for you and your friend group, Sean Ryan, Hound & Hammer boots founder and Rag & Bone sales associate, suggests going even more informal. “A house party means you can stay comfortable and casual,” he emphasizes. “You wouldn’t want to wear anything so nice you’d worry about spilling on — nothing beats jeans and a tee. Then, make it holiday fun by throwing in some red or green, or wearing an ugly sweater. This also means you can wear your Vans.”

The Company Christmas Party Look
If you work in a casual environment and the office holiday party follows those same expectations, Ryan suggests a simple approach. “Depending on the vibe of your office, you’ll probably wear something similar or nicer to what you’d have on amongst your peers during the week,” he says. “Trade the ugly sweater for a casual collared shirt, unless your office is cool like that, and consider swapping in chinos or cords, as opposed to jeans, and bust out the desert boots or chukkas, which are a tad more presentable than your day-to-day sneaker.”

Feeling more fashionista? Gallagher has two suggestions, the first being what could be categorized as a rocker look — that is, “a leather jacket, a tee, worn-in black or charcoal jeans and motorcycle boots.” If that’s way off your personal style, Gallagher says a patterned ski sweater, a T-shirt, slim chinos or trousers and either suede loafers or wingtips without socks is a less conspicuous option (although, going sockless in the middle of December is going to look pretty damn conspicuous anywhere outside of, say, Florida). 

On the other hand, if your office Christmas party is more on the formal side, Gallagher recommends wearing either a velvet or fine corduroy sport coat with a pocket square, a dress shirt, slim trousers or chinos and a pair of suede loafers. Yeah, it’s a little over the top, but you’ll definitely be eye-catching (this may or may not be a good thing, depending how you normally act at the holiday party).

The New Year’s Eve Party Look
Assuming, again, a very fancy party (because otherwise, let’s face it, New Years’ is just a wipe-clean free-for-all), Gallagher suggests bringing your blazers out from the back of the closet: Try a black blazer over a navy blue crewneck sweater, distressed dark grey jeans and boots. If you’re feeling especially dressy, Gallagher says black tie attire — aka a black or navy dinner suit — is the way to go. Or, if you want to stand out as the most festive guy at the party, your other option is to “wear a navy jacket with a black lapel and black trousers, or a plaid jacket with a black lapel and black trousers,” she says.

Ryan has a similar suggestion, although he does recommend checking in with the host or other party-goers before showing up in something too fancy. “A good host would give you a heads up if you needed to suit up,” he says. “But if you have the option and pieces, a sports coat with a nicer T-shirt or button-down shirt without a tie is a safer bet. Wearing the blazer gives you the flexibility to dress up in a comfortable, casual look with dark denim pants. However, I generally believe that you can’t be overdressed for an event like that unless you’re a nut in a tuxedo when someone told you a collared shirt and jeans were fine.”