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The feverish swirl of bubbling 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 festivity you partake in (American Thanksgiving, Christmas, Hanukkah, annual viewing of The Muppet Christmas Carol), the end of the year tends to deliver copious joys and pitfalls alike, and as such, a wardrobe prepared for the spray of intimate dinners, office parties, holiday shindigs and snowy romps is a prerequisite for cutting down on the undue stress of getting dressed this winter.
The unfortunate news? 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 fully understand that you have gifts to commandeer, rinks to skate, flights to inevitably be delayed, cocoa to consume. (Oh, and end-of-year deadlines to meet…but who’s counting?)
To that end, we have, with a little help from UK-based retailer Mr Porter, shouldered the heavy task of curating sensible yet stylish looks appropriate for whatever the festive season flings your way. Thanksgiving dinner with the in-laws? New Year’s Eve Bash? We have it all covered. Below, exactly what you should be wearing this holiday season.
The Festive Family Dinner
A great dinner starts not with the food, but with the folks; regardless of your turkey-adjacent faculty as host or guest, a uniform that could be appropriately described as “cozy” feels appropriate for all but the most buttoned-up of family affairs. This mantle should have little bearing, however, on your ability to flex on your mouth-breather cousins or impress your Chanel-pilled aunt. Opting for classic fall fair is encouraged — a deceptively pliable Merino rugby from menswear bastions Drake’s or magnanimously pleated corduroy pants should suffice.
Pro tip: Indulge generously…in both food and ‘fits. Opting for naturally looser pieces will pay dividends post-thrid slice of pecan pie.
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 already complicated enough, the average annual holiday party tends to lob a total sartorial curveball your direction to accompany the blazing fastball of boozed-up coworkers and the topsy-tervy slider that is navigating holiday bonuses with your crossfaded boss at the Karaoke afters. (Three strikes — ‘yer out!) Does the ratio lean business or casual? Is a Christmas tree-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 ribbed turtleneck (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 vibe.
The Year-End Blowout Bash
New Year’s Eve demands your annual best. For the sartorially cautious, this typically translates to a crusty velvet blazer. You’re better than that, sir. A whole new year is cause for celebration, after all — try something infinitely bolder, like a funky flannel suit, or patent leather footwear or a luxurious crimson cashmere. 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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