Fashion

The 5 Most Awkward Thanksgiving Weekend Encounters—and What to Wear to Them

Thanksgiving weekend is here. It’s time to eat copious amounts of home cooked food…and try as hard as possible to avoid everyone else back in town. Between family outings to the movies and last-minute runs to the supermarket, awkward encounters with people from your past life are all but inevitable. These holiday run-ins are much worse when you’re wearing a 2-day old topknot, high school soccer team hoodie, and flannel pajama pants. Do yourself a favor and come prepared—we’ve got you covered with five outfit ideas, ahead.

Bumping into your ex at the grocery store.

Your mom sent you out to get some last-minute additions for the Thanksgiving table and, wait a minute, is that? No. YES, it is: Your high school boyfriend of two years right there in aisle 12. Whether you choose to stop and cringe-chat or reduce your interaction to a “Thank U, Next” head nod, you’ll be grateful you wore a just-in-case outfit. Focus on tried-and-true wardrobe classics that fit your figure really well and are comfortable but subtly sexy.

Autumn Cashmere Off-the-Shoulder Ribbed Merino Wool-Blend Sweater, $98; theoutnet.com

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Everlane The Cheeky Straight Jean, $68; everlane.com

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Acne Studios Crossbody Mini Leather Shoulder Bag, $420; net-a-porter.com

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Nike Blazker Low LE, $57; nike.com

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Running into everyone at their mom at Starbucks—before you’ve had your coffee.

A craving for cold brew is not an occasion to try by any means. But you can throw on some items that look good and are as comfy as the flannel pajama pants you initially planned to wear. Oversized sunglasses and a baseball cap can help you avoid any immediate recognition, while a leather jacket will help you seem less of a hot mess when you are noticed. Bonus: The jacket is so good it doesn’t matter what’s underneath Heck, it could even be nothing because you were that lazy.

Topshop Leather Biker Jacket, $295; topshop.com

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Kitsch Baseball Hat, $18; mykitsch.com

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Vuori Performance Joggers, $84; nordstrom.com

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APL Techloom Phantom Sneakers, $165; shopbop.com

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Sunday Somewhere Sophiya Sunglasses, $270; sundaysomewhere.com

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Seeing whats-her-name on your old jogging route or at the local gym.

Leave the undetectable AirPods at home—you want headphones that very clearly communicate “do not talk to me.” That being said, it doesn’t hurt to look good. Bring on the color coordinated athleisure just in case you make a “You guys, you’ll never guess who I ran into!!!” guest appearance on the Instagram story of someone whose name you forgot.

Ultracor Altitude Botanical Top, $80; six02.com

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Reebok Crop Hoodie, $39; nordstrom.com

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Nike Rose Gold Metallic Air Leggings, $50; six02.com

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Beats Solo3 Wireless On-Ear Headphones, $240; walmart.com

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New Balance Fresh Foam Cruz v2 Nubuck, $60; newbalance.com

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Breakfast at home with your S.O.’s family.

You don’t want to be the only person fully dressed in jeans while everyone else is in their pajamas, but you’re not familiar enough to walk out in the ratty “home clothes” you usually sleep in (nor the sexy silk PJs you like too). Instead, enjoy those pancakes in a matching sweat set, like this cranberry-colored velvet one. Oh, and for the record: Wear a bra. It could be a comfy one!

Lively Geo Lace Bralette, $35; wearlively.com

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Hunkemoller Velour Lace Up Loungewear Hoodie & Joggers Set, $68; asos.com

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Free People Haven Cozy Crew Socks. $14; shopbop.com

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Drinks at the hometown bar where your entire high school will be.

If you need a drink at some point during Thanksgiving weekend, you may find yourself in the middle of an unofficial high school reunion at the local bar. Opt for sleek basics with an edge and accessories that say, “I’m doing juuuuust fine, thank you very much.”

Uniqlo Crewneck Shortsleeve T-Shirt, $10; uniqlo.com

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The Kooples Franky Faux Leather Pants, $195; saks.com

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Stuart Weitzman The Huxley 85 Bootie, $575; stuartweitzman.com

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Gucci Dionysus Mini Printed Shoulder Bag, $1,690; net-a-porter.com

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Aurate New York Connection Earrings, $200; auratenewyork.com

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