Dressing to Win: How to Look Like the Coolest Girl in Any Room

At the risk of sounding like a rainbow-cake-baking member of the special-snowflake generation, we will, at some point in our lives, grow into ourselves and find our respective personal styles, which will be the coolest thing of all when it eventually happens. But until it clicks and we wake up knowing exactly how to dress like a cross between J.J. Martin and Natalie Hartley and Taylor Tomasi-Hill, there are a few tricks to help us fake it as we plod along toward genuine, signature chicness.

We review them here in a guide that should be called "Everything You Ever Needed to Know About Temporary Coolness." One more thing: If you frequently find yourself being the coolest person in the room, you really should be hanging out with cooler people.

When the dress code says long, you say short (and vice versa)

In life and in style, doing what nobody else is doing generally makes you stand out. Vanessa Seward of Azzaro once extoled the virtues of longer lengths for the cocktail hour, and so did every '70s hostess in her Ultrasuede Halston. Conversely, a guipure lace mini when the other be-trained attendees are struggling to stay upright is pretty much the best black-tie move you can make.

No one said you have to wear heels

True, extra height sometimes makes for a better line, but here's what's weighing down the other side of the scale: dancing, walking outside to wherever the night takes you, impromptu parkour, embellished pointy-toe flats, Tabitha Simmons Hermiones, not being grouchy because your feet hurt and there's nowhere sanitary to sit. Plus, do you see "must strap on 6-inch stilettos" on this list? Nuh uh. 

Don't bother changing

I don't really know anyone who doesn't do this, but if you are ever tempted to change before any nighttime event that's not a wedding or Met Gala, don't give in. Stay in your work outfit and maybe—maybe—put on some lipstick in a color that's not true red. It is very "Oh, I just stopped by because I was in the neighborhood and I've got an opening before my next super-fun thing, which might be impromptu parkour because I can do that wearing flat shoes." Studied = the opposite of cool.

When in doubt, this outfit is the answer

There will be other girls wearing fur or leather jackets from The Arrivals with skinny trousers and boots, but 1) this is where your accessories and personality come in, and 2) you could recruit them for your coven. 

Mess it up—on purpose

For most of us, this is our hair, which hasn't seen brushes since 2010. For us when we have good days/time to get blowouts, this might mean just tweaking one thing about an otherwise normal or polished look to be weird or unexpected. Think a Dries van Noten trompe l'oeil lip ring with a "nothing" outfit, a Prada-esque topknot with a pretty skater dress, or turning your button-down into a J.Lo-at-the-Grammys plunge. (Emma Oak has my vote for Fashion Month's best-dressed.)

Fancy for day, simple for night

Think about it: Why do the celebrities who wear one-color, non-embellished Calvin Klein dresses stand out in your memory of red-carpet dresses? Because the norm is piles of tulle and sparkles and boobage. Making your day and night wardrobes interchangeable might mess with how much you *enjoy* your clothes (science says the more you use something, the less you like it), but 1) MASS reductions in cost-per-wear, 2) fashion keeps moving in this direction, and 3) why wait? Life is too damn short to not wear sequins whenever you can—unless you're at the Oscars. 

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