A Guide to the Coolest Cocktail Attire for Men

There’s something about the inevitable cocktail party — the evening of the regional conference, a best friend’s housewarming, or celebrating the opening of, well, just about anything short of a rehab clinic — that demands not only a handy list of witty stories and pop culture references, but also a clean, sophisticated outfit that accentuates the formality without losing the fun. You’ll want to wear something that befits balancing precocious stemware with business cards and passed hors-d’oeuvres. It’s that one moment where you want to be more Cary Grant than Hugh Hefner. More Johnny Cash than Elvis Presley. 

Let’s talk about what not to wear. Yes, it’s an evening of frivolity. That does not mean that it’s time to dress like a clown. Just say “no,” to novelty neckwear (and keep saying it). Ties with little cocktail glasses on them are best left in the closet. 

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Yes, Tom Cruise wore Hawaiian shirts in Cocktails. Yes, that was also 1988. This is a slippery slope, especially since prints are pretty hot right now, but trust us on this one: until we open the beach house, these are a solid “no.” 

White jackets. Black T-shirts. Vests. Suspenders…here we speak from experience. There is nothing more embarrassing than being at an event where somebody hands you an empty glass (well,unless she’s asking for a refill or implying it’s time to head for more intimate environs). Do not wear anything that might make you look like a cater waiter or bartender, no matter how hip the stir. Unless, of course, you are the hipster bartender or up-and-coming model/actor, in which case, have at it. 

Maybe most important? Think about your date! She does have one up on you: the classic little black dress is a woman’s secret weapon for just about any cocktail party, but guys don’t have quite the same firearm in their arsenal. Make sure that whatever you’re wearing let’s her shine, even if the evening is all about you. 

Cool Cocktail Attire for Gentlemanly Drinking

Hugo Boss Trim Fit Solid Wool Suit – $895
cool cocktail attire for men attired hugo boss suit blue

Brevity is the soul of wit and its sartorial equivalent is this suit: simple, elegant lines in a two-button, notch lapel model. It’s done in an elegant blue that’s dark, but not too formal, and that looks good on just about anybody. If you don’t wear it to work you’ll wear it to other, less formal gatherings for seasons to come. 

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Ted Baker London Solid Skinny Silk Tie – $95
cool cocktail attire for men attired ted baker skinny tie magenta

Solid, but with textural interest to make it interesting. A burgundy color to suggest the evening’s libations. In fact, we like just about any darker, jewel tone, especially for winter parties. Lighten it up a bit after Easter to celebrate warmer days to come, but don’t think that “lighten up” means pastel. It doesn’t. 

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Charles Tyrwhitt Triangle Weave Dress Shirt – $110
cool cocktail attire for men attired charles tyrwhitt dress shirt

Again, a simple color, with a bit of texture. It’s more interesting and more casual than a starched white dress shirt, and you’ll get bonus points for finishing the look with a pair of elegant cufflinks. 

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J. Crew Black Onyx Sterling Cuff Links – $88
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If you didn’t inherit Great Uncle Beau’s set of matched diamond cufflinks and studs, grab this classically styled pair from J. Crew. They’ll be your workhorse for French cuffed shirts, lending just the right level of formality without being fussy or pretentious. 

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Florsheim Fuel Plain Toe Oxford – $120
cool cocktail attire for men attired florsheim dress shoe leather blue

Keep the footwear dressy, but we like this offering from Florsheim because it offers not only a colorful, yet subdued, look; it’s also fully cushioned, with a removable footbed, dual-density EVA midsole for cushioning and rebound responsiveness, and a durable rubber sole for comfort. After all, if the party’s a good one, you’re gonna be on your feet for a couple of hours. Be kind to your dogs. 

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Kenneth Cole V-Neck Sweater – $110
cool cocktail attire for men kenneth cole v neck sweater gray

Should the evening feel just a bit more casual, take it down a notch by swapping out the shirt and tie for this V-neck sweater. It not only looks great, but the silk and cotton blend will also feel good and add a little extra warmth should certain people keep opening the window to climb out on the fire escape for cigarette breaks. 

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Naked & Famous Dobby Dungaree Shirt – $146
cool cocktail attire for men attired naked  famous button down shirt

Knocking it down one more level of casual, we like this “Dungaree” shirt because the navy still keeps things refined, while the Dobby weave softens things up. Wear it under the suit jacket or pair it with your favorite pair of colored jeans. 

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A.P.C. Petit New Standard Jeans – $210
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Without going all Bruce Springsteen, “Born in the USA” on us, yes, a pair of jeans can be a complex alternative for the cocktail affair. Check with your date—if she’s showing up in that classic Audrey Hepburn heartbreaker, this won’t work. But if she’s going a tad more casual, try these crisp, dark jeans from A.P.C. They’re cut a bit narrower through the hips to the ankle and made from mid-weight selvedge denim. Pair them with any of the shirts above.

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To Boot Alek Grey Suede – $350
cool cocktail attire for men attired to boot loafer gray suede

This soft calf suede loafer is going to be your go-to shoe this year. They are as comfortable as your bedroom slippers, but the silhouette is low-slung and as streamlined as a Jaguar F-Type. They’re inherently casual, but class up a pair of jeans and add nonchalance to a nattily tailored suit. 

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And now that you know what to wear to cocktail hour, don’t you think it’s time you learned how to make a good cocktail?

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