Home for the Holidays: What to Wear When You ‘Accidentally’ Bump Into People From Highschool

Written by Greta Felton

One of the most anticipated nights of the year is just around the corner. It’s not Thanksgiving or Christmas—this is far more crucial to a 20-something’s social calendar: Black Out Wednesday. The night when everyone you love and loathe from your teenage years congregates in the same overcrowded, under-lit bar. While adrenaline is arguably the best accessory, looking your absolute best is a close second. Stuck on outfit inspiration? Don’t worry—here are some closet essentials that are effortless yet eye-catching for B.O.W.

Trousers - Nothing says sophistication and confidence quite like a sharp pair of trousers. Opt for heathered greys, navys, opal-browns, or classic black for those indecisive moments. A sleek leg with a pleat practically announces, “I know what I’m doing with my life, and you should be grateful to witness it.”

Monochrome Outfits - Monochrome never goes out of style. Coordinated tones show an eye for simplicity and elegance while signaling subtle fashion knowledge. Bonus points if you mix textures within the same color family for extra dimension.

Kitten Heels – Winter boots may be the obvious choice, but a dainty kitten heel strikes the perfect balance between chic and practical. Comfortable enough to navigate crowded bars yet instantly elevates your look, they’re a small power move.

Fringe – Want to stand out? Add a touch of fringe for movement and personality while everyone else goes for streamlined, tailored silhouettes. A little unexpected flair goes a long way on a night like this.





Layers – When in doubt, layer it out. Throw a dress over trousers, mix textures, or stack accessories. Multiple layers add depth and interest while giving you versatility if temperatures, or moods, shift.

Statement Outerwear – Your coat may be the first thing people see, so make it count. Think loose blazers, vintage trench coats, faux fur jackets or, my personal favorite a sleek motorcycle leather jacket. Bonus points if you get to announce you “thrifted it abroad.”  

Comfort Meets Confidence – Above all, wear something that lets you feel like yourself. Confidence shows louder than any outfit detail, and no one wants to see someone fidgeting with a constricting ensemble while the gossip flows.

Edited by Ruby Her and Galilea Matus

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Ditch Your Black Puffer: 6 Vault-Approved Jackets to Elevate Your Winter Wardrobe