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. 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: Bonobos Unconstructed Italian Wool Blazer in Burgundy – $400. Santa, baby! Channeling our inner-Michael Scott for a classy but casual Christmas. Seasonally appropriate, but still works year-round. Exceptional comfort. Probably (definitely) the best item Bonobos has in their catalog. Was just on sale for 30% – 35% off during the Black Friday / Cyber Monday corridor.

The Shirt: Banana Republic Merino Long-sleeve Polo in Black – $53.70 ($89.50). Long-sleeve polo shirts are “in” right now, so take advantage of a trend that actually skews toward timeless, for once. Great fabric and cut that accentuates a more athletic frame. It will lend a casual look under a sport coat, and will stand out in a sea of V-neck and crewneck sweaters.

The Pants: Banana Republic Athletic Heathered Traveler Pant in Smoke Grey – $58.80 ($98). More BR, but they do a lot of foundational items very well. These are my favorite pants I own; great stretch, cut, and feel to the fabric. These are worth the full price, but being BR, you won’t ever (like, ever) have to pay it. And even if you did, you’ll get great mileage from these beauties.

The Coat: Spier & MacKay Charcoal Wool/Cashmere Overcoat in Charcoal – $398. Outerwear is something you should splurge on, or at least be ready to shell out for, to get an actual durable-good with a proper cut and features. Spier & MacKay, among others, excels in this department. Charcoal is a great option for a do-it-all coat. Looks great dressed way up too.

The Watch: Orient Bambino 2nd Generation in Black/Black – $150. Simple, beautiful, refined. Orient excels at bang for the buck automatic timepieces, and this entry in the Bambino lineup for only $150 is one of my favorites.

The Belt: GAP Basic Leather Belt in Black – $17.94 w/ GAPCYBER & GOBIG ($40) The beloved GAP leather belt, but in black.

The Boots: Cole Haan Waterproof Wakefield Chelsea Boot in Black – $200. Chelsea boots being featured in a Dappered style scenario. I know, you’re shocked! But these, while spendy for Cole Haan, are waterproof, have soles with grip, and should be plenty comfortable. A do-it-all fall/winter boot. For something cheaper but still waterproof, try CH’s Kennedy.

The Scarf: J.Crew Abraham Moon Wool Scarf – $48.65 w/ SPLURGE ($68). A great way to add a pop of color to an otherwise understated outfit.

The Socks: Allen Edmonds Herringbone Merino Cool Dress Socks – $14.97 ($19.50). Temperature regulating and made in the USA.

The Gloves: Banana Republic Wool-Blend Snap Gloves – $59.10 ($98.50). Wool on the top side, with leather palms. The glove mullet! Only, this actually works. Not too dressy, but not puffy insulated either.

The Gift: Colonel E.H. Taylor Small Batch Bourbon – appx $40. Don’t show up empty-handed. Since we’re leaning into the “smart” in smart-casual, opt for something out of the box, yet still, y’know, “nice.” Instead of wine, bring a standout bourbon. For about $40-$45, Colonel E.H. Taylor’s Small Batch Bourbon is tough to top. Bourbon is aged for approximately seven years in barrels located in the original storehouse built by E.H. Taylor, instrumental in building the American bourbon industry and the pioneer of the Bottled in Bond Act, the nation’s first real advertising law. It helps that it’s a delicious nip of dram, too.

About the Author: Jason P. is a Dappered devotee, having curated the majority of his wardrobe through the site. He is an enthusiast of wool sweaters, chino pants, and affordable automatic watches. In his free time, you can find him at his boxing gym or antiquing with his wife. 

Coming up Monday: A style scenario for a much more dressed down/laid back get together. Need something fancier than the above? That was yesterday.