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, icy blues, grays, and 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.

The Sportcoat: Bonobos Italian Cotton Knit Blazer – $298. The key to pulling off a great smart casual outfit is layering. And an easy wearing sportcoat is many a man’s best friend. Unlined back for comfort.

The Shirt: Tie Bar White Pinpoint Dress Shirt – $44 ($55). Or whatever your favorite crisp white dress shirt happens to be. Favor a smoother pinpoint or twill fabric. A thicker oxford might get hot. Tie Bar is running a 20% off sale through tomorrow, 12/7, and thus the sale price on that wheelhouse/foundational white dress shirt.

The Pants: J.Crew 440 Slim or 770 Straight Cords in Navy – $88. As we said above, casual pants like cords and chinos will pair well with a sport coat and will help to dial down the formality level. Texture looks great during the colder months, so choosing moleskin or corduroy over a flat chino fabric can be a great way to go. Two different fits available for the J. Crew option, and they’re often if not always on sale.

The Pocket Square: Banana Republic Factory Patterned Pocket Square – $14 ($35). Pocket squares should compliment, not totally match. So this navy option with the warmer tones of the pattern will do more than fine. Or if pocket squares aren’t your thing, just skip it all together.

The Watch: Orient Bambino Bauhaus in Gray – $135. Minimalist. Sleek. And the gray works great with the blues and browns of the rest of the outfit. And no, your watch strap doesn’t always have to match your shoes and belt. This still works. A watch that gets leaned on a lot. Because it looks and feels really good. Especially for the price.

The Socks: Bombas Merino Wool Slope Socks – $24. Warm and well cushioned since the weather outside is frightful. Fun looks in case the party is at someone’s place and it’s a strict “shoes off at the door” household.

The Belt: Nordstrom Newman Reversible Leather Belt – $49.50. A basic, reversible, do-anything dress belt. Ships and returns for free.

The Boots: Thursday “Duke” Chelseas – $199. Chelseas for easy on/off if you have to take them off at the door. Boots in case they’re staying on and you guys start to hop from one place to the next. Rubber studded sole for traction. Just make sure you break them in well in advance.

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 in, 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 much more dressed down/laid back get together. Need something fancier than the above? That was yesterday.