While it may seem like ‘cocktail attire’ is an empty phrase stamped on every invitation—one that serves no purpose but to make you agonize over the uncertainty of its sartorial meaning—consider it in the context of the event details and it may start to make a bit more sense. Take into account the event purpose, in addition to the time and place. Your best friend’s wedding will require very different attire than a corporate event or fashion party. Furthermore, an event taking place at a swanky hotel will call for a dressier outfit than something held at a restaurant around other non-guests/patrons, and definitely more so than a party held at someone’s home. Check out the hours, too—evening start times typically suggest a more formal fête than those scheduled earlier in the afternoon or day.
Photo: Miguel Reveriego

While some hosts like a private affair, others create their own hashtags and would feel utterly offended if you didn’t tag them. Always dress like the paps will be there, but make sure you’re clear on whether the event is social-media friendly or not.
Photo: Mariano Vivanco

If your host/hostess is known to be old-fashioned or traditional, dress more conservatively than you would if the host were especially avant-garde. Your fashion editor friend will likely have a more relaxed interpretation of cocktail attire than your boyfriend’s Republican parents.
Photo: Ditte Isager

Choose an ensemble that is appropriate for the time of year and style it accordingly. A colorful floral number and strappy sandals might be just right for a springtime soirée, while a winter event will likely call for closed-toed shoes and an evening coat. Editor’s tip: A touch of fur is ultra-glam for cold-weather months. If it’s around the holidays, the dress code tends to open up to include options with a festive bent (think metallics and siren red).
Photo: BFA

In a season of red, green, velvet and anything shimmery, you can’t go wrong with a great black silk slip dress. It’s elegant, easy and foolproof. Sleek hair is its best accessory.
Photo: Getty

While you don’t have to go for overall sequins, one standout item like shoulder-sweeping crystal earrings will help take your outfit up a festive notch. Keep the rest of the look streamlined but elegant and let your bijoux do all the heavy holiday lifting.
Photo: Getty

Appropriate lengths fall somewhere between mid-thigh and mid-calf. Save floor-skimming gowns for black tie affairs, and definitely reserve dangerously short minis for nightclubs and bachelorette parties.
Photo: Getty

The English love a good fascinator, the French still opt for berets, and Rihanna is embracing the bucket. While the idea of donning a hat for an evening affair sounds like a throw-back, it feels truly modern right now. Have fun with your toppers and take a fun fashion risk this holiday season.
Photo: Getty