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 is for looking pretty darn sharp. Not tuxedo-fancy, but the occasion calls for getting dressed up. And this is a two-for-one scenario. Two options for a dressed up holiday party. You’ll see why. (Top Photo by Juliana Malta on Unsplash)

 

For the (stylistically) daring

The Sweater: Express 100% Merino Turtleneck – $52.80 ($88). OH BOY. Turtleneck and suit (no chains please). It’s the sex panther of the style-world. Fascinating. Alluring. Deadly. Okay maybe not “deadly,” but it’s all but guaranteed that someone (or more likely multiple someones) will comment on the obvious fact that you’re wearing a turtleneck with a suit. Why that’s the case, it’s unknown, but turtlenecks have an undeniable magnetism for commentary. Both for good and bad. 100% merino here, so it’ll breathe. Which it’ll have to. Because by the 17th time someone says “oh you look so DAPPER!” you may find your blood temperature start to elevate ever so slightly.

The Suit: Banana Republic Italian Nailhead Wool Suit Jacket & Trouser = $360 ($600). Or whatever your preferred gray or charcoal gray suit happens to be. Just not a light summer gray. These Italian wool suit separates from Banana Republic are pretty great (see the review here,) when they’re on sale. Which they are (40% off!) through today, Wednesday 11/29/23. Make sure you leave time for any possible alterations to get that fit dialed in.

The Watch: Orient Bambino 38mm – $270. Orient’s new slightly smaller, sleeker, more refined on the wrist flagship dress watch. See the full review here.

The Socks: Made in the USA Darn Tough The Standard Mid-Calf Lightweight Lifestyle Socks in Charcoal – $26. 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 Blake Stitched Cap Toe Oxfords with Rubber Sole – $160 ($178). Recently restocked and (for now) are still getting a Cyber Week 10% off discount at checkout. (UPDATE: Spier extended their Cyber sale through Sunday 12/3.) They’re sleek, they’re made well, and the materials used are quite nice for the price. That and the subtle, rubber sole will help keep you upright on slick sidewalks and stairs. Full review here.

The Belt: Banana Republic Italian Leather Belt – $54 ($90). Or whatever black dress belt you have on hand.

 

For the not-as-daring

The Shirt: Tie Bar Solid Texture Light Grey Dress Shirt – $60. A shirt & tie combo is the obvious choice for those who don’t want to hear “Nice turtleneck!” a million times throughout the evening. But we’re going with a grey shirt here instead of white or light blue. That grey shirt choice will help avoid the “I just came from the office” look, as it instead anchors the look in an evening/cocktail feel.

The Tie: Tie Bar Barberis Wool Floreale Burgundy Tie – $35. Seasonally appropriate while still being (very) subtle. Italian wool fabric.

The Pocket Square: Tie Bar Solid Emerald Green Pocket Square – $12. More subtle seasonal appropriateness. If the burgundy tie/green pocket square partnership is a little too “holiday-y” for your tastes, skip the square.

The Suit: Banana Republic Italian Nailhead Wool Suit Jacket & Trouser = $360 ($600). Or whatever your preferred gray or charcoal gray suit happens to be. Just not a light summer gray. These Italian wool suit separates from Banana Republic are pretty great (see the review here,) when they’re on sale. Which they are through today, Wednesday 11/29/23. Make sure you leave time for any possible alterations to get that fit dialed in.

The Watch: Orient Bambino 38mm – $270. Orient’s new slightly smaller, sleeker, more refined on the wrist flagship dress watch. See the full review here.

The Socks: Made in the USA Darn Tough The Standard Mid-Calf Lightweight Lifestyle Socks in Charcoal – $26. 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 Blake Stitched Cap Toe Oxfords with Rubber Sole – $160 ($178). Recently restocked and (for now) are still getting a Cyber Week 10% off discount at checkout. They’re sleek, they’re made well, and the materials used are quite nice for the price. That and the subtle, rubber sole will help keep you upright on slick sidewalks and stairs. Full review here.

The Belt: Banana Republic Italian Leather Belt – $54 ($90). Or whatever black dress belt you have on hand.