Image: Miguel Reveriego
1. Pay attention to the information you’re given.
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.
Image: Ditte Isager
2. Keep the host in mind.
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.
3. Dress appropriately for the season.
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).
4. When in doubt, simplify.
If you’re afraid of being overdressed, understand that casual is not its opposite. An minimalist slip dress is an elegant option that won’t run the risk of looking overly fancy or informal. Adorn with jewelry and statement accessories for extra glamour—you can always remove and stow them in your purse if need be.
5. Skip extreme hemlines—in either direction.
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.
6. Go beyond the LBD.
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.
7. Tread lightly when it comes to trends.
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.
8. Cocktail parties aren’t just for cocktail dresses.
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.
9. When it comes to handbags, less is more.
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.
10. Put your best face forward.
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.
Image: Alexi Lubomirski
11. Comfort is key – to a degree.
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.
12. Rules can be broken, but only with the utmost consideration and care.
There is no single blanket statement that can be applied without exception—there’s a time and place for everything. For example, a cascading boho maxi for a beachside summer soirée: totally appropriate. A supremely elegant pair of flats for an evening affair: tricky but doable. But showing up to a wedding wearing white, or an upscale cocktail party in jeans and sneakers? Not okay—not now, not ever.
Image: Terry Richardson
13. Don’t be afraid to ask.
If you’re at a total loss, check in with the host/hostess to clarify the appropriate level of dress.