Style Scenario: What to Wear to a Dressed Up 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. It’s holiday party season, and we’re going to tackle three different style scenarios in the coming days, each depending on how swanky the party you’re headed to happens to be. This one isn’t tuxedo-fancy, but the occasion calls for getting dressed up. Protip: If you’re buying a new suit (or sportcoat) for a party this year: be sure to leave plenty of time to get it tailored. Most tailors are pretty swamped right before the holidays. (Top Photo by Juliana Malta on Unsplash)

The Suit: J. Crew Ludlow Traveler Slim Fit Suit Jacket + Matching Trouser = $487.20 ($696). Cool blues are an underrated color-set for the holidays. Everyone else is probably gonna be in dark gray or black. So blue is a stylish move. It’s also a really good suit. Lightweight, temperature regulating Italian wool is year-round appropriate, but won’t suffocate you in over-crowded restaurants or halls. Half canvas construction. Fabric has a bit of stretch woven in for comfort. Sold as separates, so if you’re (very) lucky, you may be able to get away with very little or even no tailoring.

The Shirt: Banana Republic Wrinkle Resistant Dress Shirts in Slim or Standard Fit – $48 ($80). Shown here in a size medium slim on 5’10″/180. Good collars on these shirts. Fabric is wrinkle resistant, 100% cotton. A bit of ironing may be needed by most, but it irons up easy and doesn’t come out of the dryer looking like a wreck. The one major drawback (and it’s a dealbreaker for some) is that despite being dress shirts, they’re sold in “alpha” sizes like small, medium, large, etc. Although they do offer a tall template, for our vertically blessed folks out there.

The Pocket Square: (via Amazon) King & Priory Navy & Dark Green Check – $12.99. Seasonally appropriate. Wool fabric. Cheap.

The Watch: Tissot 40mm PRX Powermatic 80 Green Dial – $850. Integrated bracelet watches are having a moment. They’re sleek, they look modern and interesting. And a super-luxury version even had a small role in one of the biggest movies of 2025. Unlike the movie watch, this Tissot won’t cost you thousands upon thousands. It was even on sale over Black Friday. 40mm case size, and a slim 10.9mm thickness. Dark green dial is perfect for the evening. The less expensive alternatives: Citizen Tysoya – $332.50, Orient Bambino 38 – $214.20

The Socks: USA Made Darn Tough The Standard Mid-Calf Lightweight Lifestyle Socks in Navy – $27. Midweight for warmth, all merino for breathability and moisture wicking. As comfortable as you’ll find for a pair of dress socks. “Versatile terry loop cushioning under the foot and below the ankle.” They really are worth the twenty six dollars.

The Shoes: Spier & Mackay Cap Toe Oxfords – $208. Studded rubber sole for traction on winter streets, platforms, and sidewalks. Blake stitched. Well made. Fair price.

The Belt: J. Crew Italian Leather Belt – $39.75 ($79.50). Or whatever black dress belt you have on hand to match your shoes.