Next Level: B&W Gingham

Wearing gingham doesn’t mean looking like a picnic blanket—especially when you go all black and white. Here’s how to play it cool. —erica
LEVEL I: Doesn’t get much easier than this loose Steven Alan top. Toss on some chunky gold jewelry to jazz it up.
LEVEL II: Friends & Associates thinks you need a fresh alternative to a denim mini. We’re with them.
LEVEL III: Some major peplum action, to really amp up your weekend look, from Roseanna.
LEVEL IV: Totally fair if you thought you’d never wear a tankini again—but this Pret-a-Surf situation has the power to change your mind.
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Next Level: Varsity Jackets

These days, you don’t have to earn a letterman jacket—you just have to want one. And, dear god, do I. Here, four that knock it out of the park. —erica
LEVEL I: This 10 Crosby Derek Lam puppy has a blazer-like quality that makes it especially easy to rock—like, picture it with a pencil skirt.
LEVEL II: The tweed on this Roseanna one is all deconstructed and French-y. Bonus: It’s a total black-brown switch hitter.
LEVEL III: Spring training, the Rag & Bone way.
LEVEL IV: WHOA, Clover Canyon! But how ridiculously cool would this be with white jeans?!
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Next Level: Lips

In honor of V-day, y’all, —erica
LEVEL I: Delfina Delettrez shows your wrist a little love.
LEVEL II: Who says you gotta stick to red and pink? Roseanna gets all moody with her black ‘n blue print.
LEVEL III: Lizzie Fortunato demonstrates that SWAK works even better if you employ embroidery.
LEVEL IV: Markus Lupfer—never the type to hold back.