Skip to main content

The Manual may earn a commission when you buy through links on our site.

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.
Image used with permission by copyright holder

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.
Image used with permission by copyright holder

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.
Image used with permission by copyright holder

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.
Image used with permission by copyright holder

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.
Image used with permission by copyright holder

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.
Image used with permission by copyright holder

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.
Image used with permission by copyright holder

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!
Image used with permission by copyright holder

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?

Editors' Recommendations

John Jones
John Jones is a Jersey City, New Jersey-based writer who enjoys covering design in all its forms, from fashion to…
This is what Citizen Watches has in store for 2024
From pocket watches to anniversaries, here is Citizen 2024
Citizen 100th anniversary pocket watch

Citizen watches are some of the most popular on the market for one very big reason. They are experts at offering all of the best features and styles of ultra-expensive luxury brands like Rolex, Omega, and Patek Philippe without forcing you to mortgage your house to land one on your wrist. Every year, the Japanese powerhouse reaches new levels of success with innovative, attractive, and accessible designs. In 2024, the brand is looking to continue that trend with a slew of updated and celebratory designs.

Something to notice about the collection of new releases hitting the shelves this year is that Citizen is celebrating two big anniversaries that will surely have you looking to upgrade your collection with some beautiful throwbacks. Here are the new releases (that we know of so far) to keep your eye on in 2024. Citizen always has surprises up their sleeves, so there is definitely more coming this year.
100th Anniversary Pocket Watch

Read more
If you’re looking for the best men’s cologne, try these recent drops
Smell your best with these great fragrances
A person spraying cologne on themselves.

You only get one chance to make a great first impression. That is why we dress nicely. That is why we groom ourselves expertly. And that is why you need to have a great cologne. You never know who you are going to meet, and you don't want to be caught in anything other than your best. You may be forgiven if your hair is a little long when you are on the trail. You may be forgiven for having a five o'clock shadow on Saturday afternoon. And you may not be punished for wearing jeans and a T-shirt at the movie theater. However, you will always be judged for not smelling good. That is why you need to invest in the best men's colognes.

Having a pleasant fragrance is more than smelling pleasant for those around you. It also attracts people to you and shows that you care about your hygiene. People will respond better and remember you fondly if your smell lingers. It is the most powerful scent tied to memory, so make sure you are remembered in 2024 with these top picks for colognes for men. We didn't go with all the big boys in the men's cologne industry. You will see one name that nearly everyone knows. But, we stuck more with the ones that you all should know. There is no Dior, no Polo, and no Gucci on this list. We didn't go for names. We went for quality fragrances and picks that will keep you remembered long after you leave.
Fulton & Roark Cloudland

Read more
Adidas just kicked off a big sale – Up to 40% off sneakers and shoes
Running in Adidas shoes.

Looking for great sneaker deals? Look no further than Adidas which currently has up to 40% off many of its shoes and sneakers. If you’re looking for new footwear, this is your chance to do so while saving plenty of cash. Buying a few pairs right now would be a great idea so you’re all set for the coming months. With hundreds of items in the sale, hit the button below to check out the sale for yourself. Alternatively, keep reading and we’ll take you through some of our favorite deals.

What to shop for in the Adidas sale
The best Adidas running shoes are pretty special so why not check out the which are down to $180 or $120 for members, instead of $200. The shoes are coded for forward motion with an updated 3D-printed Adidas 4D midsole with a new lattice structure. It transforms impact forces into forward motion and is combined with great traction from the Continental Rubber outsole. There’s also adaptive Adidas Primeknit which is teamed up with light and breathable mesh so your feet feel comfortable at all times.

Read more