Style Scenario: What to Wear to a Dressed Down 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 parties that are more beer, cookies, & board-games, and less cocktails, appetizers, and schmoozing.

The Pants: Old Navy Slim Ultimate Built-In Flex Chinos in Red Raisin ‘ $18.90 w/ HURRY ($39.99). A bit unexpected, but the red color is perfect for the holidays. Subtle and on the dark side to keep it dressy, lest people ask you if you stole Santa’s pants. Little bit of flex for that extra cookie you’ve been eyeing up, too. Go for it.

The Shirt: Bonobos Unbutton Down in Grey Herringbone – $47.60 FINAL w/ PRESENTTIME ($88). The subtleness of this pattern makes it present as a light grey shirt from a distance, but up close, you can see it has some nice visual detail.

The Watch: Timex Expedition Scout Chronograph in Brown/Natural – $60.45.  I prefer a higher-visibility watch face when wearing a dark sweater; it makes it stand out against the sleeve. Love this one from Timex.

The Scarf: Banana Republic Donegal Wool Scarf in Red Wine – $47.70 ($79.50). Why not match your scarf to your pants? Live your life.

The Sweater: J.Crew Merino Wool Snowflake Shawl Cardigan – $100.98 w/ MONDAY ($198). Because if you can’t have fun with your sweater at a dressed-down holiday party, where can you? Kick your boots up in this cozy, chunky merino wool number, complete with (somehow not cheesy) snowflakes. Plus, the weight of the shawl should keep the unbutton down’s spread collar under control.

The Jacket: Gap ColdControl Lightweight Hooded Puffer Jacket – $82.80 ($138). Lightweight and airy enough to slide over your chunky sweater should you need it. The hood is a nice touch in case it’s extra nippy out to keep down the chill factor.

The Cap: Amazon Goodthreads Marled Beanie in Burgundy – $15. Dark enough in color to separate it from the pants and scarf visually, but still gives just a little bit of color pop.

The Belt: Express Single Prong Buckle Belt in Cognac – $39.90. Simple. Can’t really go wrong here.

The Socks: Wigwam Merino Wool Comfort Boot Socks in Charcoal – $15.00. Wool is your best friend when it comes to boots – it wicks moisture so your feet aren’t swampy, but still keeps you toasty warm if you’re standing outside for a bit.

The Boots: J.Crew Kenton Captoe Boots in Burnished Tobacco ‘ $126.48 w/ MONDAY ($248). Grippy and handsome, these will happily trek you from icy sidewalks to a back porch holiday beer swap.

The Host/Hostess Gift: Shiner Holiday Cheer Dark Wheat Ale. An old-world dunkelweizen (dark wheat ale), this beer is quite simply my favorite beer around the holidays. Roasted pecans and Texas peaches make for a lighter and fruity drink, so this is not your typical winter warmer where you have one and then need to sit down for a while.

About the Author: Ryan N. is a professional web developer for (and alum from) the University of Delaware, who keeps a close shave as to not be confused with his strongly-bearded twin brother. He plays guitar and drums, loves going to concerts with his wife, and loves being a dad.

Ryan N

Recent Posts

30% off Todd Snyder, Nordstrom Early Black Friday, & More – The Thursday Sales Handful

Steal Alert: Allen Edmonds 5th Ave. oxfords for $199. Leather or Dainite sole. 1st quality,…

21 hours ago

Style Scenario: Thanksgiving – Casual

For the casual get together where the "table" is a plate on your lap, and…

1 day ago

The 2024 Dappered Holiday Gift Guide for Her

Something Wicked, hugs in jewelry form, a different kind of cupcake, and more.

2 days ago

Banana Republic Factory 60% off + additional 20% off Black Friday Preview

Blazers in poly/wool blend for $63. Surprisingly great traveler jeans for $38. Lots more. Math…

3 days ago

Style Scenario: Thanksgiving Smart Casual

Hitting the middle ground for the upcoming holiday feast.

3 days ago

In Review: Hamilton Field Khaki Quartz Watch

In person with Hamilton's new 38mm, quartz powered field watch.

3 days ago