Style Scenario: What to Wear to a Smart 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. It’s holiday party season and we’re going to tackle three style scenarios in the coming days depending on how swanky the party you’re headed to happens to be. This one is for the somewhat dressed down affairs that might be out, or might be at someone’s house. The key is to keep things tailored but relaxed. You aren’t closing a business deal, but you are aiming to make an impression. And while red and green are obviously the colors that get seen the most during this time of year, saturated blues and crisp white are a classy way to mix it up. That’s what we’ll do here, so you don’t show up looking like a wayward elf. (Top Photo by Anton Shcherbakov on Unsplash)

The Sportcoat: Olive Texture JC Penney Stafford Wool Blend Sportcoat – $96 w/ GIFTALL6 ($120). Green without being elf green. Sharp without being expensive (we’ll spend some cash on some other items in this outfit). Texture without being tweed, which can look more casual/professorial.

The Shirt: Ledbury Sanders Non Iron Fine Twill Made to Order Shirt – $135. Or whatever your favorite crisp white dress shirt happens to be. But good gracious is the Ledbury shirt with it’s mid-spread collar and slightly lowered second button perfect for this type of look. Note that these take 2-3 weeks for delivery (as they make them once you input your specs), but figured some of us might have picked up one of these when they were 35% off for Black Friday. Now’s the time to put it to good use once it arrives. The Less Expensive Option: Spier & Mackay Fine Twill Dress Shirt – $58

The Pants: GAP Corduroy Slim Pants in Dark Night Blue – $18.90 w/ GREAT ($69.95). Dark blue cords (as opposed to brown) look rich. They’re almost velvet, but clearly not velvet. Again… rich. And these are under twenty bucks with that extra 30% off code. The price is decidedly not rich.

The Pocket Square: Bonobos Skating Penguins Pocket Square – $29 FINAL ($55). The bleepin’ pocket square costs ten bucks more than the pants. What is going on here? BUT IT HAS TINY SKATING PENGUINS ON IT. This is stupid.

The Watch: Dan Henry 1937 Dress Chrono – $270. Interesting and versatile, the 1937 from Dan Henry can be dressed up or down. Which makes it a smart choice for an outfit that’s both stylish and not overly dressed up. Reviewed here in the silver dial option.

The Socks: Made in the USA Darn Tough The Standard in Navy – $29. The best, most versatile socks on the market.

The Boots: Allen Edmonds Hamilton Weatherproof Oxford Dress Boot – $349 ($495). Far from cheap, but they’re basically a bot version of the Strand only weatherproofed and on a studded rubber sole. If you like to dress up, these could become something you reach for, often, between now and April.

The Belt: J. Crew Leather Belt with Tartan Cloth – $39.50 ($69.50). Is this too much flair when combined with the (skating) penguins pocket square? Whatever. It’s the holidays.

The Gift: A bottle of brown booze or an N/A alternative – $50 or less. Always bring a small gift for the party host if possible. If they’re a whiskey fan, the options are immense. If they’re getting a jump on Dry January, try the Ritual Rum alternative. Big fan of that stuff as it makes a great alcohol-free hot toddy. Two slices of lemon squeezed into some tea (Trader Joe’s fall harvest tea works great), and a solid glug of the Ritual rum. Hangover free. It’s a pretty amazing feeling once you get the hang of not drinking at social events.

Coming up tomorrow: A style scenario for a more dressed down/laid back get together. Need something fancier than the above? You can find that here.