My Looks

Speakeasies and Spilled Pears

Yesterday was fun.


Well, first of all, I got to wear this. It’s a 1930s dress that my Nanny Ruth gave to me years ago, but that I’ve never had a good reason to wear until now. So that was neat.

Incidentally, you may have noticed that I’ve been wearing some vaguely period-appropriate pieces for some of these shoots…but I’ve been trying not to make them look too “costume-y.” So let’s talk how to do that!

– No retro ‘dos: A nod to the period you’re working with is nice, but pairing a vintage dress with a period-appropriate hairstyle starts veering into too-much territory. Try loose waves, a clean updo, or a relaxed topknot.

– Keep your accessories streamlined: Since your vintage piece will pull the focus, don’t go too overboard with accessories.

– Since vintage pieces don’t always fit quiiiiite right (you can’t exactly ask the salesperson to grab you a different size), feel free to get creative: I’ve worn a three-sizes-too-big vintage slipdress with a boyfriend-style blazer over it (to hide the gaping armholes), and frequently cinch oversized dresses with belts or wear undersized dresses as tunics with opaque tights and boots.

– Try unexpected pairings, like a floral Victorian blouse with leather pants, or a full ’50s skirt with a simple white man’s undershirt on top.

– Feel free to mix eras: If you wear a ’50s hat, dress, gloves, and shoes, you’ll look like you’re headed to a Halloween party. (In the above shot, I’m wearing a ’30s-style dress, ’40s-style (sorta) heels, and ’60s-style sunglasses.)

– If the whole thing makes you a little nervous, start simple: a vintage silk blouse with jeans or some great retro jewelry are easy ways to take the look for a test-run.

A couple more reasons why yesterday was fun:

I hung out at a speakeasy on the Lower East Side to film a segment for JITH (above, I’m with our lovely intern, Ansley).

Oh, and then I came home and discovered that pears apparently taste better when placed directly into one’s hair. (The teeth!)

Segment wardrobe: Vintage dress, belt, and jewelry, Juno heels, Juicy Couture sunglasses, Inge Christopher clutch.

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