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The feverish swirl of anticipation — or state of near panic, depending on your affinity for extended-family gatherings and pine-scented candles — can mean only one thing: the holiday season is here. No matter what manner of festivities you partake in (Christmas, Hanukkah, annual viewing of The Muppet Christmas Carol), the end of the year tends to deliver copious joys and pitfalls alike. As such, a wardrobe that can manage intimate dinners, office parties, holiday shindigs and snowy romps is a prerequisite for cutting down on the undue stress of getting dressed this winter.
With all the moving pieces, constructing a festive closet is no easy feat. What does one wear to a “business-casual office party”? Does “black tie” really mean “black tie”? Carving sweater or ugly holiday knit? Fret not — we understand that you have gifts to commandeer, rinks to skate, flights to take that will inevitably be delayed, cocoa to consume. (Oh, and end-of-year deadlines to meet…but who’s counting?)
To that end, we have shouldered the heavy task of curating sensible yet stylish looks appropriate for whatever the festive season flings your way. Cursed office party? New Year’s Eve bash? We have it all covered. Below, find exactly what you should be wearing this holiday season.
The Dreaded In-Law Dinner
The end of the year is a time for great cheer…and a time to host the in-laws, whatever that might mean for you. A great impression starts not just with the Resy, but with your ‘fit. Something that says, “I’m cool, I didn’t overthink this and I need this over by 9:30 at the latest.” A pin-sharp blazer — single or double-breasted, so long as it’s classy as all get out — over a smart turtleneck shows you mean business when it comes to nabbing the check.
Pro tip: A pair of (acceptable) jeans is a great way to dress down an otherwise suited look, and a great way to stay prepared for whatever bar crawls and ice skating may spontaneously occur.
An Ode to the Carving Sweater, the Unsung Hero of Festive Menswear
You should be dressing like Dylan McDermott in the ‘90s remake of “Miracle on 34th Street” from now through New Year’sThe Office Holiday Party
As if dressing for the office wasn’t complicated enough, the average annual holiday party tends to lob a sartorial curveball your direction to accompany the blazing fastball of boozed-up coworkers and the topsy-turvy slider that is navigating holiday bonuses with your crossfaded boss at the karaoke afters. (Three strikes — ‘yer out!) Does the vibe lean business or casual? Is a naughty Santa-emblazoned tie camp, or liable to get you sent to HR?
We can’t speak to your office specifics, but here’s what we’ll say: nobody likes a try-hard, but nobody likes a Grinch, either. Unless your office is managing billions, skip the tie and telegraph your holiday cheer appropriately with a chunky, possibly patterned sweater (an agnostic holiday-season staple, if there ever was one) or otherwise festive — but not too festive — knitwear.
Pro tip: Nervous you’ll end up over, or worse, underdressed? Deposit a white dress shirt and tie at your desk in the days prior — should you need to change, it should suffice for nearly any occasion.
The Year-End Blowout Bash
New Year’s Eve demands your annual best. For the sartorially cautious, this typically translates to a velvet blazer. But you’re better than that, sir. A whole new year is cause for celebration, after all — try something infinitely bolder, like a discretely funky (it’s all in the lapels) suit, a floral tie or a luxurious silk shirt. Hell, try all three. For auld lang syne, right? Champagne comes out easy, anyways.
Pro tip: Should you be heading out for the evening, remember the double jeopardy rule — whatever the temp outside, a packed, fevered interior could end up twice as warm. All of which to say, ditch the coat unless you really need it.
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