7 Steps To Mastering Cool-Girl Style

Let’s start with a disclaimer: I am not claiming to be cool, and if you saw my collection of Hanson band tees, the subject wouldn’t even be up for debate. Rather, through my daily perusal of countless street style sites (nobody said I don’t have a cool job), I’ve come to notice some signature styling nuances common to a crop of women—editors, muses, It-girls—who are definitely considered cool. Just what are their secrets?

Scroll on to find out, as I try out seven of their go-to tricks.

Step 1: Wear a statement accessory.

Photo:

Pepe Leon for Who What Wear

Front-back earrings are definitely having a moment. They’re the kind of accessory that make you do a double take.

Shop My Earrings: Pamela Love Five-Spike Stud Earrings ($275) in Rose Gold

Step 2: Add a personal touch.

Photo:

Pepe Leon for Who What Wear

I adorned my blazer with vintage pins I found at the flea market, but I also love the idea of embroidering your initials on a jacket in a discreet spot.

Shop A Similar Pin: Karl Lagerfeld Vintage Initials Brooch ($504)

Step 3: Scrunch your sleeves.

Photo:

Pepe Leon for Who What Wear

Nothing looks more laid-back than a pushed-up sleeve.

Shop My Blazer: Zara Striped Blazer With Belt ($100) in Ecru/Navy

Step 4: Add a subtly sexy element.

Photo:

Pepe Leon for Who What Wear

The majority of a cool-girl ensemble should look insouciant and slightly tomboyish, but a hint of allure, achieved by my lacy camisole, keeps the look intriguing.

Shop My Camisole: Cami NYC The Racer Camisole ($138) in Black

Step 5: Half-tuck your shirt.

Photo:

Pepe Leon for Who What Wear

Yes, this tuck was carefully crafted, but it’s supposed to look anything but. Get step-by-step instructions here.

Shop My Jeans: ​Citizens Of Humanity Premium Vintage Corey Crop Jeans ($274) in Renegade

Step 6: Wear your cross-body bag inside your jacket.

Photo:

Pepe Leon for Who What Wear

Similar to tucking your hair into your shirt, wearing your bag as a layer beneath your outerwear is an unexpected touch that adds a lived-in feel to your look. Bonus: The look is also an effective anti-theft technique.

Shop My Purse: Elizabeth And James Cynnie Micro Cross Body Bag ($295) in Pink Beach

Step 7: Opt for flats over heels.

Photo:

Pepe Leon for Who What Wear

While heels certainly have their merits, a flat looks unforced, especially when it’s an of-the-moment slide.

Shop Similar Sandals: Ancient Greek Sandals Thais Pony Sandals ($270)