Style Scenario: What to Wear to a Dressed Down Holiday Party

About the Author: Brandon D. is a trial attorney for the government living in Houston, Texas. He’s a new dad (#girldad for those of you who do hashtags), which has made working from home that much more interesting for him, his wife, and their dog Charlie.

What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. First we went dressed up. Then it was somewhere in between. Now it’s time for a dressed down, but still put-together look for those holiday parties that are more beer, cookies, & board-games, and less cocktails, appetizers, and schmoozing.

The Shirt: BR Double Knit Longsleeve T-shirt in Smoke Gray – $50 ($64.50). Layering is good for weathering the cold outside, but inside and around a lot of other people? Some of us like to wear just one shirt if we run warm. In Smoke Gray, this sweater like tee will either let the whimsy pants be the star of the show or pair well with navy cords. You could always throw it over a white button down for an upgraded athleisure kinda/sorta look (thanks to the raglan sleeves and curved hem of the t-shirt)

The Pants: Bonobos Holiday Drawstring Pants in Sasquatch – $119. I’m a big believer in the theory that your outfit for a party should not equal “what I wore to work” plus “but later.” That’s where pants like these come in, especially the Sasquatch option. They’re fun and festive, and with an elastic waist, should also be extra comfy. Sizes are limited though, and if you don’t want to spend over a hundred bucks on pants you’ll likely wear only a few times a year (if that), then J. Crew’s 770 straight fit cords in navy should do the trick.

The Scarf: Banana Republic Shadow Plaid Wool Scarf – $70. Since it’s plaid, it’s winter holidays-appropriate. But since it’s gray and black, it’s also any other time of year you’d need a scarf-appropriate too. As you might have guessed, I’m a fan of versatility.

The Jacket: Uniqlo 3D Cut Seamless Down Parka – $149.90. For those extra-cold evenings, a hooded down jacket should give you the warmth you need.

The Belt: Banana Republic Italian Leather Belt in Cognac – $59.50.  See the scarf re: versatility. It’s a standard, quality belt. That’s quite useful, holiday party included.

The Watch: Timex Milano XL 38mm Leather Strap Watch – $79.20 w/ JOLLY20 ($99). It’s well reviewed, inexpensive, and with a cushion case, just different enough to get you noticed.

The Socks: GAP Cozy Socks – $3 ($7.95) OR J. Crew Merino Wool Socks in Heather Glen – $19.50. If you’re at a house party and the host/hostess has a “no shoes in the house” policy, now is the time to show your holiday spirit with the GAP cozy socks. If there’s no such policy or the party is at a bar/restaurant the J. Crew socks should do you well. Still festive (the green option), and since they’re merino, they’ll be useful most other times you need dress socks.

The Boots: Banana Republic Tanner Chelsea Boots – $178. Classy even with the lug sole, dressy enough for most work places, and no laces? Yes, yes, and (now that I’m a dad and don’t have time for laces) yes. Alternatively, if you want to keep it cozier you could go with Allbird’s Wool Loungers. So comfortable that you might not even need socks. If you don’t have a pair of house shoes, these should be on the list.

The Host/Hostess Gift: Flor de Cana 4 Rum – $17.99. For making Coquitos: To be sure, if you’re getting alcohol with no intention of mixing it, maybe opt for something more expensive (see the alternate/upgrades).  But if you want to bring over a fun, holiday drink, your host and fellow party-goers will surely appreciate this eggnog alternative.

The Board Games: Telestrations – $28.99, Monikers  – $24.99, Wavelength – $34.99, Cash n Guns – $39.95, or (checks notes) Secret Hitler – $35. No one needs to tell you about Monopoly and I’m not an expert on (relatively) new board games.  But one of my friends is obsessed.  As in, he goes to board game conventions and collects rare and unique games as a hobby.  So when I asked him what games were great for a holiday party, and his recommendations included “a fast-paced game of deception and betrayal,” (the last one) I knew I asked the right person.