Weather Vain - Key West, Florida - 72 and Partly Cloudy

One of the warmest destinations in the U.S. of A. today: Key West. What to wear if you don’t HAVE to wear a jacket. —erica
Clockwise from top left:
+ The sort of five-o’clock-somewhere pants from See by Chloe that leave plenty of room for Kermit’s key lime pie.
+ So, it’s not supposed to be a super-bright day, but this is definitely the sort of place where sunglasses—these by Karen Walker—are part of the uniform.
+ Stripes! On your soles! Alice + Olivia sandals that can navigate the rocky beaches.
+ A silk Tibi tank that goes with the motif of the Southernmost House.
+ Mociun earrings as quirky as your surroundings.
+ The low tonight: 64. So you can get away with just a Rag & Bone scarf-slash-shawl if you want to.
+ A wicker clutch from Rebecca Minkoff that’s a fun as it is easy—goes well with the catch of the day at the Flaming Buoy Filet Co.
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Next Level: Neoprene

Neoprene is not exactly an EASY material, so trying it is all is definitely taking a leap. But on the rainiest days, its slickness becomes even more tempting. Here, four ways to go that won’t make you feel like an extra in The Life Aquatic. —erica
LEVEL I: Phillip Lim’s answer: Go with a belt. Put this on with the closest LBD, and you nail not only the neoprene thing but also the black-and-blue look.
LEVEL II: The color and fabric of this Tibi dress are tricky, but the so basic, super-flattering cut makes up for that big-time.
LEVEL III: Alexander Wang gives the bomber an extra hit of coolness—as if it needed the help.
LEVEL IV: Yes, there’s a lot going on here, but what if you pulled this Elizabeth & James floral situation on with a big, fluffy gray sweater? Now, there we go.
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Next Level: Metallic Sleeves

Bill Cunningham thinks it’s all about black leather sleeves. We’re with him (evidence!) and are willing to push things further: How’s about metallics? Here, four with-black ways to go. —erica
LEVEL I: This Generation Love top’s super easy in a Saturday-with-Serena van der Woodsen way.
LEVEL II: Tibi gets lacy without going too girly—tough to do.
LEVEL III: Why not do metallic AND leather, c/o this Aiko shirt? Marc Summers double dares you.
LEVEL IV: You (and David Bowie) would look so freaking fly in Maison Scotch’s take on the black moto jacket.
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In Character: Rainbow Bright

You know who’s not scared of color? This girl. And while it’s going to be tough to round up your own Sprites, you can follow her anti-gloom dressing mantra, fighting dreary days with your mad-good style. —erica

This Christopher Kane silk shirt looks like it came straight from the Color Caves.

A no-nonsense blue Tibi dress—still plenty loud to piss off Murky Dismal.

Jeffrey Campbell shoes that match Starlite’s mane perfectly.