Style Scenario: What to Wear to a Smart Casual Holiday Party

About the Author: Adam Terry is a thirtysomething salesman in the HVAC and hydronics industry. He enjoys bourbon, boots, sneakers, raw denim, and working on his dad bod father figure.

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 (maybe), 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. It is a party, after all, so it would do you well to show up in style and leave your mark.

The Sportcoat: Spier & Mackay Brown Harris Tweed Guncheck Blazer – $548. The key to pulling off a great smart casual outfit is layering. Start with a sport coat or blazer on top, preferably in a simple check, herringbone, or textured fabric in a versatile color family. This will take the outfit up a notch in formality, but not so much that you’ll look like a boring business person. I prefer earth tones like browns, tans, greens, blues, etc. as they tend to pair well with less formal pants. Now, half a grand isn’t cheap. So if you want to scale down the cost and maybe lean on a cooler gray, this Grey Glenplaid Super 120s Vitale Barberis Wool Flannel Blazer from BR has been going on sale a lot. Drops to $240 when 40% off.

The Watch: Timex x Todd Snyder Marlin Date Watch – $259. Whether you’re a “watch guy” or not, we can all agree that a nice watch on your wrist can make the outfit just a bit better. Personal budgets are wildly different, so whether you can afford a Timex or a Rolex, we’re looking for something that’s super versatile like this Timex x Todd Snyder collaboration watch. The silver case, champagne sunburst dial, and cognac leather strap all work well with our overall aesthetic and won’t stick out like those big, black G-Shock watches.

The Sweater: J.Crew Cashmere Crewneck Sweater in “Burnt Saffron” – $128. Everyone expects you to wear something in a shade of red or green during the holidays. Don’t be afraid to go rogue and be bold! I’m a fan of this rich, eye-catching shade of yellow that’s all too close to being sued by French’s.

The Shirt: J.Crew Broken-In Organic Cotton Oxford Shirt in White – $56.25 w/ FLASH ($75). Keep the outfit grounded with a simple white Oxford cloth button-down shirt. A crisp, clean white Oxford looks great on everyone, so use that as your base layer. If you tend to run warm and sweat in too many layers, swap the Oxford shirt out for a thinner, breathable option like J.Crew’s “Secret Wash” shirts.

The Pants: J.Crew 770 Straight Fit Pants in “Saddle Brown” Corduroy – $66 w/ FLASH ($88). As we said above, casual pants like cords and chinos will pair well with a patterned sport coat and will help to dial down the formality level. I’m a big fan of texture, so I tend to choose moleskin or corduroy over a flat chino fabric. Keep the overall color palette in the same Earthy realm as the jacket, but opt for a slightly toned down shade of medium to dark brown. Think tobacco or mocha.

The Scarf: J.Crew Solid Cashmere Scarf in “Graphite” Grey – $35.20 FINAL w/ FLASH ($98). If you live in an area where it gets chilly enough for scarves and gloves, see if you can scoop up something in a neutral shade of grey like this solid cashmere number from J.Crew (which has been, as of late, dirt cheap with sales). This will pair well with everything without being distracting. I know a bold buffalo plaid or blackwatch tartan pattern is tempting, but those are a little harder to pair correctly with other patterns.

The Gloves: J.Crew Tipped Lambswool Gloves in “Charcoal” Grey – $29.62 w/ FLASH ($40). See above. These gloves are “tipped” with the tech-friendly fabric that should allow you to text and tweet while keeping your little mitts toasty warm.

The Boots: Astorflex Greenflex Chukka Boots in “Dark Chestnut” – $198. Chukka boots are the Swiss Army Knives of a man’s closet. Depending on the shape, material, and color, they can be dressed up and worn with a suit or dressed down for casual weekends in jeans. For our style scenario, let’s wear a pair in a rich, dark brown suede for some added texture. If you picture a tree, these boots are the roots at the bottom of the trunk, giving weight and structure to the outfit. A darker shade here will help the other elements visually stand out.

The Belt: Nordstrom Men’s Pebbled Leather Belt in Brown – $69. Every person old enough to tie their shoes should know that you pair the color and overall aesthetic of the belt to that of your shoes. The colors and materials don’t have to be an exact match; you’re trying to establish a consistent narrative between the different garments. I love this pebbled leather belt from Nordstrom because it adds a subtle layer of visual texture without distracting your gaze.

The Socks: Smartwool Everyday Heathered Rib Merino Wool Socks – $22. The “Rule for Socks” says that you should try to match the color or shade of your pants, not your shoes. The theory is that, should your socks peek out, you want the appearance of longer pants, not taller shoes. The caveat to this rule is if you’re going for a sock with a pattern where you want a little pop of color. Be careful with this, though, as you don’t want to be  the “weird socks guy” right? Play it safe and stick to a solid or mostly solid color sock with simple patterns.

The Gift: Bourbon, Rye, or other Whiskey – $50 or less. Always bring a small gift for the party host if possible. As a whiskey fan, I try to bring an inexpensive bottle of whiskey instead of a cheap bottle of wine. I find whiskey to be more interesting, especially single barrel products that can help generate a fun conversation about our flavor palates. Your local liquor store probably has a handful of single barrel “store picks” available for less than $50. If all else fails, just remember: no one has ever complained about being given a box of chocolate chip cookies and a bottle of Wild Turkey 101.

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.