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What to Wear to a Holiday Party

Beau Hayhoe
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So, you’re wondering what to wear to a holiday party … we’ve got not one, but two ways to help you with that. The best menswear to put on for a holiday party is a tricky balance, a blend of classic pieces you know and love, plus ones with a bit of flair. For the man who likes straightforward, sharp classics, we’ll show you how to style a crisp cardigan with winter-ready boots. And for the guy who dresses with holiday fun in mind, the second outfit in this feature ought to do the trick nicely. Check what to wear to a holiday party off your list of concerns this season — we’ve got you covered.

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The Classic Outfit

  • The Sweater: Abercrombie & Fitch Cardigan – $98
    Abercrombie & Fitch does a great job making simple, subtly stylish staples — this cardigan, with just a bit of holiday flair, is a prime example. It’s the perfect antidote to any ugly holiday party sweaters.
  • The Dress Shirt: Mizzen+Main Kennedy Dress Shirt – $125
    Crisp, sharply tailored and easily wearable the rest of the work week, the Kennedy Dress Shirt from Mizzen+Main is anything but ordinary. Again, it’s the proper response to the guy who might have a laughing snowman on his sweater.
  • The Trousers: Mizzen+Main Vice President Charcoal Chino – $135
    Going with a look that’s a bit more tailored this holiday season? This refined pair of charcoal chinos has your name all over ‘em.
  • The Tie: Seize Sur Vingt Dark Navy Herringbone Tie – $140
    Leave the holiday printed novelty tie at home — at least, that’s our recommendation. This classic tie is supremely well-made — the sort of tie James Bond might pair with a charcoal suit. That means it’s more than suitable for your holiday party.
  • The Watc: MVMT Watches White Gold Classic Watch – $110
    It’s tough to find a subtly stylish watch that doesn’t cost a boatload — this handsome rose gold watch from MVMT leaves you plenty of money to splurge on a fine bottle of wine for your holiday party host (or yourself).
  • The Boots: Johnston & Murphy Conard Wingtip Boots – $179
    Navigating winter’s treacherous terrain is no fun — Johnston and Murphy is here to help with stylish, affordable wingtip boots.
the fun outfit
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The “Fun” Outfit

  • Bonobos Capstone Italian Wool Tuxedo Jacket – $700
    Now, for the man who wants to dress with a bit more pep in his step this holiday season … we think this tailored, well-made Bonobos tuxedo jacket is the perfect starting point.
  • J. Crew Everyday Cashmere Cardigan in Deep Navy – $148
    It’s different than a black vest or a cumberbund, and because we’re having fun with this outfit … that’s a great thing. This cashmere cardigan provides both warmth and visual interest when it comes to an extra layer against the chill of winter.
  • Bonobos Jetsetter Stretch Dress Shirt – $128
    There’s virtually no wrong way to wear a sharp white dress shirt — that’s great news for you, because this simple option lets the striking tuxedo jacket do the talking.
  • The Tie Bar Solid Satin Bow Tie – $19
    A holiday party calls for only your best ensemble, right? And there’s nothing sharper than a neat twist on a black-tie ensemble — this satin bow tie echoes elegant refinement.
  • Brooks Brothers Regent Fit Blackwatch Plaid Pants – $248
    Here’s perhaps the most “fun” part of this outfit — a pair of blackwatch plaid pants that exude vintage cool and a dash of sly style. Plus, who doesn’t love getting dressed up in tailoring from Brooks Brothers?
  • Allen Edmonds Carlyle Plain Toe Oxford – $395
    Because this outfit is based on a few statement pieces, there’s not a more elegant style move than black Oxfords for a smooth finish — Allen Edmonds makes some of the best out there, perfect for your holiday party.
  • Daniel Wellington Classic Sheffield Watch – $229
    To keep the focus on the plaid pants and burgundy tuxedo jacket — as sharp and stylish a combo as any — reach for a cleanly designed dress watch that’s a statement in and of itself.

Special thanks to our friends at Raven & Rose and The Rookery Bar in Portland, Oregon for allowing us to use their beautiful and historic restaurant and bar as a backdrop for our photo shoot. 

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Beau Hayhoe
Beau Hayhoe
Former Digital Trends Contributor
Beau Hayhoe is a freelance men's style writer, consultant and PR pro based in Brooklyn. Beau's menswear and gear writing has…
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