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What to Wear to Cocktail Hour: The Coolest Cocktail Attire for Men

Three people dancing around a table.
Photo by Monstera from Pexels

Remember the sound of ice tinkling in glasses? Remember polite conversation that wasn’t happening over a laptop or a tablet? Remember evenings that started out as slightly stiff and civilized that eventually got downright friendly and (if we were lucky) just plain fun? Stop living in the past, because if all goes as planned, the holiday cocktail party is about to make its return. This season the festivities may not be as big, nor as crowded as they used to be, but we’ll be the first to raise a glass and welcome them back.

We’re happy to see old friends, make some new ones, and, along with that, dress up and strut our sartorial stuff once again. Let’s be honest, though, the rules have changed. We have learned that looking good does not necessarily forgo being comfortable. Today’s style takes a page from a mid-century Hollywood script, with nary a tie in sight, but still no less thought-out and put together. Here are a few ideas for what would catch our studied eye from across a crowded room.  

ASOS Design Plaid Oversize Suit Jacket & Pants

man sitting in a chair in a brown plaid suit and tan shirt.

This slightly oversized jacket and trouser combo with an exploded plaid pattern reaches across time to give a retro feeling that’s kinda 1950s, maybe a little Roaring 20s, and all with a dash of the 1980s. It’s just the right attitude for a party, and we also love that it’s sold as separates (the trousers are $57) so you can go as loud or as quiet as you like, and come out with a better fit. It is not your father’s corporate uniform, but who’s to say that if the pieces were broken up and paired with say khakis or a leather jacket that they might not now work just as well for the office? 

Collars & Co Cutaway Collar Polo White Shirt

man with a beard in a white polo talking on a mobile phone.

This shirt features all the comfort of a polo, blended with all the formality of a dress shirt. This may end up getting the prize for best new shirt. Collars & Co. offers a series of mostly solid polo shirts executed in a woven stretch fabric that features four different dress shirt collars. We think this cutaway collar has a particularly formal look that, again, has a retro flair. Wear it with a sport coat, under a sweater, or on its own. 

Fresh Clean Tees Black Crewneck T-shirt

A black crewneck T-shirt is a wardrobe workhorse.

A minimal black or navy T-shirt can be the party-goer’s best friend. It brings a sort of elegant nihilism to just about any outfit, the casual equivalent of a tuxedo. If it’s warm enough, and you’re in great shape, wear it alone. Otherwise, it’s a great layer, making a neutral, tailored suit a little more casual, a pair of khakis sexier, or a simple cardigan more dignified.  

William Murray Brook Lines Pants

Bill Murray, the actor, now has his own golf apparel collection.

The motif on these trousers pays homage to the iconic Brooklyn Bridge, a favorite New York City spot of actor and golfer Bill Murray. We like the tasteful gray… Best yet, beyond party night, these pants offer moisture-wicking technology, wrinkle resistance, and breathability, not to mention a comfort-stretch waistband so you can enjoy holiday treats without too much worry. 

Amazon Essentials Men’s Standard Long-Sleeve Polar Fleece Shirt Jacket

This gray polar fleece shirt jacket is perfect for winter layering.

There’s an inherent cool in a classic denim jacket, but even when it’s done in dark denim it has a pretty casual vibe. We like this shirt jacket because it channels that ease, while the mottled gray fleece gray poly adds almost scholarly propriety, but best of all it’s also nice and warm. Beyond the party, it’s a comfy layer for cooler days and perfectly at home in the office. 

Ami+ Felted Wool Sweater

A great turtleneck complements most men.

A great turtleneck sweater is practically a requirement for a winter wardrobe, and this one from Ami+ may be the ultimate statement of the form. In chic black, it’s accented with a perky red graphic. It’ll dress up a pair of jeans, layer nicely under a winter blazer, and come in particularly handy if a cool weather party happens to wander out onto a patio or deck to keep the party’s air fresh and clean. 

Florsheim Lodge Cap Toe Lace-Up Boot

It's boot season, so have a pair that work well for multiple occasions.

These lace-up boots skirt the edge between sporty and dressy, looking as good with your favorite pair of broken-in jeans as they might with a gray flannel suit. Besides their points for great style, they’re also a wise investment for practicality in anticipation of winter weather to come. 

Pair of Thieves Boot Crew Socks 3 Pack

Got boots? Get boot socks!

OK, honestly, we’re not fans of much novelty anything. The ugly Christmas sweaters. The precious neckties. The cheeky underwear. The cute socks. We know it’s rather Scrooge-like, but we’ll give them all the bah-humbug. Give us something colorful, maybe textured, and — okay we’ll just say it — tasteful, and that puts us right in the holiday mood. This 3-pack of socks fits the bill perfectly, and won’t get funny looks if shoes are shed in favor of warming toes around a fireplace. 

Now, how ’bout those cocktails?

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