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 Chore Jacket: J. Crew Cotton Moleskin Chore Jacket – $96.50 ($198). Chore jackets are excellent. They’re great when you don’t want to put on a blazer or even swazer, yet still want an additional layer and LOTS of pockets to put things. This one in a deep green, super soft moleskin fabric does the trick and then some for this style scenario.

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 Sweater: Nordstrom Washable Merino Crewneck Sweater – $89.50. 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 on its own under the blazer. The cheaper alternative: UNIQLO Extra Fine Merino Crewneck – $39.90 (be warned: these are thin.) 

The Jeans: Target Goodfellow Slim Fit Jeans – $36: Inexpensive, and they can sometimes be had for less when on sale.

The Watch: Timex Expedition Scout 40mm – $31.79. Cheap, rugged looking, casual, and it tells the time.

The Belt: GAP Leather Belt – $22 ($44.95). The inexpensive standard. Or whatever brown belt you wear all the time.

The Socks: Smartwool Everyday Light Cushion Merino Wool 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. Always, yes, but especially during winter.

The Boots: J. Crew Kenton Chelseas – $209.50 ($298). Deep reddish-brown leather uppers. Subtle studded rubber sole. Goodyear welted. And most importantly: slips on and off easily in case you’re headed to a house party with a “no shoes past the front door” rule. Sometimes you just don’t know until you show up and see the pile of discarded footwear near the front door.

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. And take it from someone who has hosted his fair share of house-parties: The clean up is always significant. Some of us have dear friends who get… feisty after a couple. A drink during clean-up would be appreciated. If your host/hostess doesn’t drink, try some tea or nice coffee or even breakfast treats for the following morning.