The era of social distancing hasn’t ended the cocktail hour, it’s merely moved it indoors. If anything, happy hour is more happening than ever. One benefit that comes from domesticating our drinking is a greater freedom to indulge in cocktail attire—no, not the dreaded “cocktail attire” of vague wedding invitations or the cast-off novelty ties of Christmases past, but pieces of clothing that champion the five o’clock tipple through playful yet tasteful motifs and vintage-inspired designs that recall an earlier era of high-style entertaining.
Whether you’re looking to elevate your nightly Negroni on the couch or add a bit of flair to your next Zoom happy hour (or ours, every Thursday at 6pm EST), the ten options below will prove an excellent complement to your next dram.
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Rowing Blazers Harry’s New York Bar Rugby
Image Credit: Rowing Blazers You may not have the chance to visit the legendary Paris watering hole (and birthplace of the French 75) anytime soon, but you can visit it vicariously by pulling on this super heavyweight rugby featuring the bar’s nattily dressed bar fly mascots.
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Stubbs & Wootton Martini Slippers
Image Credit: Stubbs & Wootton There’s never been a better time to invest in a quality pair of house slippers. Thanks to a duo of embroidered Martinis—one garnished by olives, the other with an orange twist—these cotton-velvet slippers from Stubbs & Wootton transition easily from the end of WFH and the start of cocktail hour (even if that line is blurred).
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J. Mueser Negroni Tweed Campania Jacket
Image Credit: J. Mueser This unstructured jacket by J. Mueser, made in Naples from a custom “Negroni Tweed” developed by heritage English mill Fox Brothers and WM Brown magazine, provides a more subtle way to express your affinity for menswear’s favorite cocktail. Also available made-to-order.
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Drake’s Blue Cocktail Print Silk Poplin Tie
Image Credit: Drake's About to join a digital cocktail hour wearing the same un-ironed oxford you’ve been loafing about in all day? The fix is simple: add this tie from Drake’s, which features hand-rolled blades and a print with brightly colored, generously garnished micro-cocktails. It’s subtle, but saucy.
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Polo Ralph Lauren Kon-Tiki Popover Shirt
Image Credit: Ralph Lauren This nautical, Pacific Islands-inspired popover from Uncle Ralph is best accessorized with a Zombie or a Suffering Bastard in hand, yet its muted colors keep it on the right side of the tiki bar kitsch.
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Ring Jacket Andrew Mashanov Pocket Square
Image Credit: Douglas Holt/The Armoury Put a piece of secondhand travel in your pocket with this hankie made in collaboration with menswear illustrator Andrew Mashanov and available via The Armoury. The Italian-made, cotton-linen square with rolled edges depicts two well-dressed gents sharing a drink and a cigar in a Havana bar—consider them instant company for whatever you’re having.
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Paul Stuart Smoking Jacket
Image Credit: Paul Stuart Those looking to go fully maximalist with mid-century cocktail regalia can indulge in this velvet smoking jacket from Paul Stuart, complete with a shawl collar, contrast piping and tasseled belt. All it’s missing is the fez—and a fine cigar. To further stoke temptation, it’s currently discounted as part of a site-wide sale.
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Turnbull & Asser Large Spot Silk Ascot Tie
Image Credit: Turnbull & Asser So, you’ve always wanted to adapt the rakish charm of a 1950’s cocktail party host, frosty Martini in hand and a silk ascot blooming from open shirt with aplomb? Well, now’s a fine time to practice. This silk ascot from Turnbull & Asser is as English as it gets, woven in Suffolk, hand-sewn in Kent and turned out in a large-scale polka dot pattern.
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Stòffa Lounge Shirt
Image Credit: Stòffa Featuring a camp collar, a straight hem and a relaxed fit in a silky knit piqué, this Stòffa shirt hits all the right lounge lizard notes without an ounce of sleaze. Best paired with a Hemingway Daiquiri, a pair of sunglasses and no immediate plans.
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Sid Mashburn Pajama Set
Image Credit: Sid Mashburn You can still look put-together while recovering from last night’s imbibing or fixing a hair-of-the-dog Bloody Mary—so long as you do it in a smart pajama set. This matching kit from Sid Mashburn is made from 100% Portuguese plain weave cotton and features a pair of patch pockets for stashing Advil.
