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. To the long-time readers of this corner of the web… a tieless suit is pretty familiar. But just because it’s been done before doesn’t make it the wrong play. BUT. What if you really want to get fancy? Or the occasion calls for going all out? Here’s one way to do it this year, whether it be at a swanky Christmas party, or a big time New Year’s Eve event. Coming up tomorrow: A style scenario for a smart-casual party. Not quite as dressed up. Then we’ll move on after that to a much more dressed down/laid back style scenario for a holiday get together… 

The Jacket: J. Crew Ludlow Shawl Collar Velvet Blazer in Atlantic Navy – $149 w/ MONDAY ($298). Half off, extended one more day. To me, if you’re going to a holiday party or a wedding, it means you’re not wearing something you’d wear to work. And a velvet blazer is, by definition, party/wedding appropriate and something no one (well, almost) can wear to work.

The Pants: Lands’ End Tailored Fit Year’rounder Wool Dress Pants in Dark Charcoal – $44.97 w/ SLICK ($89.95). If you’re getting a niche jacket, try to make the rest of your outfit from wardrobe staples. And if you already own a solid, dark gray suit, those pants will do just fine.

The Shirt: Lands’ End Tailored Fit Spread Collar No Iron Supima Pinpoint Dress Shirt in White – $29.97 w/ SLICK ($59.95). Or, whatever your preferred crisp white dress shirt happens to be.

The Shoes: Allen Edmonds Fifth Avenue Cap-Toe Oxford in Black – $245 ($395). A band can only have one lead singer. That’s the (overly simplistic) reason why the Beatles broke up. As for your shoes (and the rest of your outfit), they shouldn’t be competing with your jacket. And these are about as subtle (and quality) as you can get. Especially for the super-marked down holiday sale price.

The Socks: Brooks Brothers Merino Wool Ribbed Over-the-Calf Socks in Grey – $22.05 ($24.50). Pricey when not on sale, but simply the best (cue the music). And if you can’t wait for them to go on sale? Again, Nordstrom.

The Belt: Nordstrom Reversible Leather Belt – $49.50. A classic dress belt. But this one is also brown when you want it to be.

The Tie: The Tie Bar Solid Satin Bow Tie in Black – $22. The most reliable option for low-priced and quality ties. If you want another brand, go for it. Just make sure it’s not pre-tied (unless you’re age seven or younger).

The Pocket Square: The Tie Bar White Cotton with Hunter Border Pocket Square – $10. No need to overthink this. A little super subtle contrast will go a long way here.

The Gloves: J. Crew Leather Gloves with Wool-cashmere Lining in Black – $49 w/ MONDAY ($98). Skip the ski gloves. Wear something thinner but still warm.

The Topcoat: Spier & Mackay Wool/Cashmere Overcoat in Charcoal, Navy, or Camel – $398. Come for their suits and sport coats, stay for their literally everything else. If any company defines affordable luxury these days, it’s them.

The Scarf: The Tie Bar Burgundy University Village Plaid Scarf – $25. They make scarves too? Since the rest of your outfit is solid, your scarf is the right place to add some plaid.

The Watch: No watch (free). Yes, no watch. It’s a party, so worry about the time tomorrow (or, you know, check your phone).

About the Author: Brandon D. is a recently married trial attorney living in Houston, TX (but will forever be a New Yorker). Brandon has been wearing a suit to work for the better part of a decade, so he appreciates the insights into quality-yet-affordable style options for which Dappered is known. When not at work, he enjoys traveling with his wife, lounging with his dog Charlie (she’s half-Chihuahua/half-Dachshund, which has the added bonus of being known as a “Chiweenie”), and the weekly trip to Costco.