Style Scenario: What to Wear to a Casual Holiday Party

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, & white elephant gift exchanges, and less cocktails, appetizers, and schmoozing. (Top Photo by Bob Ricca on Unsplash )

The Jacket: GAP Corduroy Jacket in Evergreen – $78. Holiday appropriate color without getting too bright. Light enough to wear as an extra layer, chore-jacket like, indoors.

The Sweater: Nordstrom Italian Merino Crewneck Sweater – $95. Ships and returns for free. Spendy, but washable and appears to have a decently structured neck, so it won’t look schlumpy and ragged when worn under the jacket. The cheaper alternative: UNIQLO Extra Fine Merino Crewneck – $39.90 (be warned: these are thin.) 

The Jeans: BR Factory Traveler Jeans in Slim or Athletic Fit – $42 ($105). Super comfortable with lots of stretch. 56% cotton, 25% viscose rayon, 17% polyester, 2% spandex. A real favorite.

The “Pocket Square”: Burgundy Cotton Bandana – $5.90 / 2 pk via Amazon. It’s just a bandana. A dark red bandana. Adds a splash of seasonal color, and great if you need to wipe your hands or nose or whatever.

The Watch: Timex Waterbury Heritage Chronograph – $299. Slick Panda dial looks with a more heritage leaning 39mm case diameter. Was just on sale during their 30% off Black Friday event, which was nice to see.

The Belt: GAP Leather Belt – $35 ($44.95). The inexpensive standard. Or whatever brown belt you wear all the time.

The Socks: Smartwool Light Cushion Merino Sweater Print Socks – $27. There are much, much cheaper holiday socks out there. But they’re either cotton or cotton synthetic blends, and during the holidays that’s a one-way-ticket to regretsville. Stick with wool socks. Especially during winter.

The Shoes: Made in Portugal LUCA Chukkas – $215. An investment, but the sneaker like comfort is truly something. The natural Lactae Hevea outsole is soft and springy while being surprisingly durable. Made in Portugal.

The host/hostess gift: Some sort of reserve/holiday beer. If someone is opening their home to you (a likely scenario for a casual holiday party), then don’t come empty handed. If they’re a beer drinker, figure out what type of brew they like, then get a reserve/beefed up version of that. They’ll appreciate it. And if it’s BYOB, the gift is not to be shared. It’s for them. Stick it in their pantry/cupboard. This is something for them to sip on, if they so choose, once everyone is gone and they’re cleaning up.

Joe

Recent Posts

Steal Alert: Bonobos Extra 50% off Sale Items

Smart blazers, wool outerwear, and yes... lots of pants. Free shipping & returns on much…

2 days ago

Long Weekend Winter Clearance Sales Roundup – BR extra 30% off, Nordy Rack new reductions, & More

Weekend Update: Huckberry has added new sale markdowns & styles (including some waxed truckers.)

3 days ago

Steal Alert: 1 Sale 4 Outfits – J. Crew Extra 70% off 3+ Final Sale items

4 style scenarios mined from J. Crew's mega end-of-season final-sale clearance blowout.

3 days ago

Best Posts of 2025: Series, Lists, & Advice

The how-to lists, call-backs, and tips, which made up last year.

5 days ago

Why the concept of Retail Therapy is nonsense

On trying to buy our way out of feeling bad. (No counselor's couch required.)

5 days ago

Most Wanted Affordable Style – January 2026

Suede bombers, knit "swazers," & old radium lume divers.

6 days ago