In a world where good things happen to me, I’d have a Park Avenue apartment with a spare bedroom exclusively for shoe storage. But c’est la vie—that’s not the world we live in.
Instead, I maximize my tiny closet by relying on pieces that can pull double duty for work and play, like a bra I can wear to the office *and* the gym and a pair of sneaks that take me from coffee meetings to TSA pre-check. Here, my favorite staple pieces that can go from work to weekend and back again.
These dreamy, varsity-inspired classics
HearstMade
Even if you’re not the one rigging the mast—or whatever—it’s still fun to look the part. Prep is officially back for fall, and I’m filing zero complaints (I mean that rugby-inspired striped lace…come on!). Slip into this sophisticated silhouette to stick the landing from deck to desk all season long, whether you’re headed cross-campus or off to a conference call.
Sperry Authentic Original Varsity Suede Boat Shoe
This versatile, carryall tote
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This tote will take you from office bag lady (it me) to weekend warrior. A built-in laptop sleeve, designated umbrella compartment, and plenty of planner storage (I have five…all empty) makes this tote an ideal desk mate. Plus, the Mary Poppins-level of storage and removable shoulder strap make it easy when carrying extra layers during the colder months.
Away Everywhere Bag
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The Perfect White Shirt™
This is the Perfect White Shirt™ (according to me). I wear this shirt at least once a week, both to work and on the weekend. Tuck it in, tie it up, roll the sleeves, add a jean jacket—the possibilities are endless.
Lauren Ralph Lauren Tie Front Shirt
A transformative headband
HearstMade
I get compliments on my hair every time I wear this headband (blondes do have more fun, BTW)—even when I’m pushing the limits of dry shampoo. I keep it in my desk for when I’m headed straight from the office to a fancy dinner. It never fails to soften my office style for a night out.
Lele Sadoughi Light Denim Headband
Sperry sneakers that work from office to vacation
HearstMade
Has a more perfect travel shoe ever existed? Pair Sperry’s stripey sneakers with cropped trousers and a blazer at work for edge polished yet cool edge, then swap your blazer for a light wash denim jacket before head out for a country weekend. These slip on and off with ease (and look pretty damn good doing it) so you can breeze through security for a seamless escape.
Crest Vibe Varsity Stripe Satin Sneaker
This staple skirt
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You’ve seen the memes—the leopard print midi skirt is everywhere (and not going anywhere). Get ’em while they’re hot.
The Naomi Skirt in Wild Things
A pair of do-it-all leggings
HearstMade
I’ve worn these to work, straight to the airport, immediately to bed and then to the gym the next morning. They’re super flattering, provide compression on long-haul flights, and replace at least three pairs of pants IMHO (that’s more room in your carry on for skincare).
Spanx Faux Leather Legging
Cool-but-dressy earrings
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Keep these Bauble Bar beauties in your desk dopp kit when the outfit you wore to work feels a bit meh for dinner.
Bauble Bar Faidra Acrylic Hoops
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A pair of timeless mules
HearstMade
Mules are the pinnacle of modern footwear. You get all of the style of a loafer with the comfort and breathability of flip-flops. Pair with an office-friendly midi dress for day, then slip into army green capris and a crop top for night.
Sperry Levy Tassel Mule
A fix for bad hair days
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If you’ve stretched the limits of your favorite powder-based spritz, there’s nothing a hat can’t hide. Keep this one in your filing cabinet, your glove compartment, or stashed in your go-to getaway tote when plans pop up that your roots just aren’t ready for.
Madewell Billie Rancher Hat
