What's the best reason to enjoy a cocktail, other than to enjoy a cocktail? It's a great excuse to break out your favorite cocktail dress. And if you're having trouble deciding what to wear, consider matching your dress to your drink of choice.
Kir Royale (a flute of champagne topped with crème de cassis or Chambord and garnished with a blackberry): It doesn't get more indulgent than this classic champagne cocktail, so compliment your decadent drink with a dramatic cut. A voluminous tulip skirt creates an eye-catching silhouette, as demonstrated here by the gorgeous Lucy Liu in Giambattista Valli. I adore the rosette details, and that the cut of the dress makes her resemble an upside-down champagne flute. Beyond perfection.
Pousse-Café (a layered cocktail of crème de cassis, elderflower liqueur, and pear brandy): I recently recommended this drink for my friends' wedding cocktail. A drink this beautiful and sophisticated calls for one hell of a dress. Reference this drink's delicate layers of liqueur and brandy with lush tiers and ruffles, like this delicious Gianfranco Ferré ensemble worn by Anne Hathaway. Bonus points if the layers of your dress are graduated in color, just like your drink.
Vouvray (a dry white wine with crisp fruit flavors, often with a bit of sparkle): This yummy French white wine is about as ladylike as it gets. And no one did ladylike in 2008 like my favorite new first lady Michelle Obama. Look for narrow shifts and cap sleeves. And try wallpaper florals such as this Thakoon dress that Ms. Obama wore while out working the campaign trail. Don't be afraid of extra details like bows and costume brooches. If you're feeling extra inspired, channel Blair Waldorf with a prim headband.
Classic Vodka Martini (vodka and a light splash of vermouth, shaken over ice and served in a martini glass with an olive): I used to drink gin martinis, until I woke up one day and realized that they were kind of gross. I've since switched to the vodka martini, and my taste buds couldn't be happier. When indulging in this classic cocktail, consider echoing the angles of the glass by wearing a structured dress with architectural elements. Kate Bosworth's Chanel number (actually separates, not a dress) was one of my favorite looks from 2008. When wearing a dress this lovely, you don't want to risk a red wine incident. And since martini glasses aren't exactly risk-free in the spill department, it's definitely a plus to go with something clear.
Carmenère (an aromatic medium-bodied red wine that's both fruity and earthy): A sexy red wine demands an equally sexy dress. If you're feeling daring, consider a dress with cut out details. If you're feeling fearless, go for dramatic cuts like Gwyneth Paltrow did in this Stella McCartney number. Make sure to avoid anything carbonated, as a dress this risque requires that you stand up straight. The last thing you want to worry about is whether that glass of bubbly is going to give you a fizzy stomach. And take your time on that glass, as this look requires just as much presence of mind as it does proper posture. This is a sipping dress.
Pickle Martini (cheap vodka and pickle juice, shaken, not stirred...yeah, my friends invented this): This electric green cocktail always reminds me of the fabulous 80s. Try incorporating the notorious decade of fashion into your cocktail wardrobe with puffed sleeves. Once relegated to Dynasty reruns, embarrassing wedding photos, and the wardrobe of Chloe Sevigny (bless her heart), puffed sleeves can add a playful twist to otherwise conservative shifts. Just check out how modern and un-bridesmaidy Anne Hathaway looks in her Jasmine de Milo.
Scotch and Soda (scotch and club soda, served over ice): This list wouldn't be complete without at least one reference to the fashion of AMC's Mad Men. Those women don't mess around with frou-frou cocktails. They want a stiff drink. And nothing's stiffer than a scotch and soda. Add elements of the 60s to your wardrobe with nipped waists and retro fabrics. Or go all-out with a vintage dress, kitten heels and a pillbox hat. And with all of those constricting foundation garments, stiff fabrics and unnecessary buttons, you'll be ready for a serious drink by the time you're finished dressing.
Tom Collins (dry gin, lemon juice, simple syrup, and soda water garnished with a lemon slice and a maraschino cherry): This sweet and zesty cocktail is a classic for a reason. A perfect match for fun and flirty dresses, it's a great excuse to break out the fringe. And no one does fringe better than Sharon Jones. A bit of tasseled trim here and there is a fun detail on any dress, but I recommend pairing your Tom Collins with a full-out fringed number. But be warned, this combination can lead to a night of serious dancing. It's not for the faint of heart.