I think we all bemoan the loss of the Travel Ensemble. We probably even have the same image in our minds: A woman in a slim pencil skirt and trim little blazer with a jaunty scarf, epic sunglasses and oversize handbag. Yet, let’s be honest, none of us have much enthusiasm or willingness to bring it back. No, we secretly revel in the resurgence of the legging and the oversize tee. The only time I ever dress up for a flight is if I’ll be meeting someone important on the other end, or if I’m treating it like a costume game. For example, last year some friends and I trekked out to Nantucket for a long weekend and decided to concoct our most Wasp-y ensembles for the plane. It was all fun and games until our layover in Boston, where we found ourselves completely out-Wasped by the preppiest, Yacht Club-frequenting, foppish hair-rocking pink shirt enthusiast I’ve ever seen. The man was carrying a racquetball racquet. And it got me thinking about how I’d dress for future long weekend summer engagements.
Destination: Coastal Trendy (L.A., San Diego)
If you don’t own platform gladiator sandals, go buy some. Then add super-faded (but don’t call them acid wash!) Loomstate denim and a bright, patterned, flowing blouse — one of those peasant-inspired Tucker shirts should do the trick. For gents, lace up a pair of the flashiest Nike Dunks you can find. Think neon.
Destination: West Coast Cooler-than-Thou (San Fran, Portland, Seattle)
If you’re moving up in the world (traveling for, say, a hot gallery opening or to interview for a gig with a local start-up), think dark Earnest Sewn denim (it’s so… industrial!), black Converse and old-school add-ons like a vest and an awesome hat. If you’re more into the indie-music-meets-indie-art scene, try a lightweight plaid button-down or a worn vintage tee touting some old outdoor festival only your parents could have gone to. For ladies, I’d go with an under-the-radar dress by an eco-friendly label like Mociun or Linda Loudermilk.
Destination: Preppy Points Northeast (Cape Cod, the Hamptons, Upstate NY)
There are, of course, the obvious points to hit: Navy blazer with gold buttons, faded Nantucket reds or Kelly-green shorts, a polo with the collar most decidedly flipped up, anything by Lilly Pulitzer. But about the details: consider a pinkie ring, some boat shoes or Tory Burch flats. And, if you’re really committed, a racquet.
Destination: Party Central (Jersey Shore, Miami)
I could make a lot of jokes about too-tight t-shirts, hair gel and white blazers, but I’ll keep it classy. Except for the white blazers part. Seriously, I think it’d be dope if you wore one. If you want to err on the side of flashy-stylish versus flashy-trashy, try Beckerman’s new tie-dye zip-front minidress: it sizzles without giving it all away.