Your Guide to Perfectly Executed Holiday Cocktail Attire

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.

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.

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.

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).

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.

While minimalist girls like Pernille may not be caught dead in overall sequins, one standout item like shoulder-sweeping crystal earrings takes her festive miles. Keep the rest of the look streamlined but elegant and let your bijoux do all the heavy holiday lifting.

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.

In the wise words of Karl Lagerfeld, "One is never over-dressed or under-dressed with a Little Black Dress." That being said, don't feel limited to only black options. Play with color—another element that is best informed by the time of year. For spring, a romantic pink or soft pastel. For summer go bold in something bright. For fall, rich earth tones and warm neutrals. And winter, deep jewel tones in luxe textures like satin or velvet.

Know your audience, but if the venue is casual and you're feeling like getting creative, skip the LBD, throw on some jeans, a cool top and major shoes that stand out in a crowd. You'll instantly be the coolest girl next to a Christmas tree.

Despite what you may see on the red carpet—your upcoming event may not be the appropriate opportunity to test-drive a naked dress. Or, if you're dying to try something out of the ordinary (we understand, it's not every day you get to do this) interpret the trend or look in a way that is a bit more palatable. Try a style with strategically placed sheer insets instead of something entirely see-through, or offset a plunging neckline with long sleeves.

Especially if an event takes place straight after office hours, a sleek blazer and trousers combo is an elegant look that is easy to dress up for evening. Just change your blouse (or remove it altogether) and swap your satchel for a clutch. A jumpsuit is also a great option for similar reasons.

Pick a small purse that will fit the bare essentials and opt for a handheld version like a clutch or diminutive top-handle. Cocktail events are a no-carryall zone.

Remember what Marnie said about Hannah on Girls: "She'll put on a good dress and nice shoes and then do her lipstick, and then leave her forehead shiny. It's like, you've come this far, wash your forehead!" A little light concealer or powder and a swipe of mascara are essential—and we can't stress enough the transformational powers of a good lipstick. If your hair is giving you anxiety, a low chignon is an easy, never-fail option that works for any occasion.

We rarely say this, but consider your comfort level. Parties are as much about the socializing as they are about the style, and if you're not at ease in your ensemble it will affect how enjoyable your evening is.