Coulda, Woulda, Shoulda: We Correct 5 Regrettable Fashion Faux Pas

We all have regrets. Seriously, don’t even get us started on our silver eyeliner phase or the leftover Thai food we ate this morning. However, right next to silk blouses, celebrating Cinco de Mayo, and Cadbury Crème Eggs, fashion missteps have found a special place in our regretful hearts.
So, we asked you to send us snaps of the outfits that make you wish Stephen Hawking would finally discover the secret to time travel (seriously, some of us have needs here). And the things you turned up...impressive. And since we've always got your back, we’ve decided to dream up some alternatives you can consider for the future (yes, that was a pun; no, we couldn't help it).
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As they say, hindsight is 20/20, but unfortunately, so are those traumatic Facebook photos that your friends won’t stop posting. So, read through, and consider this a primer on learning from other peoples' mistakes.
Divya and Alison are the funny ladies and avid online designer discount shoppers behind Heavy Browsing. They take fashion (and cheese and whiskey) very seriously. For more ingenious style and shopping advice, visit these self-professed silk-blouse enthusiasts on their site, and stalk them in moderation on Twitter @heavybrowsing.
1 of 5
The Scenario: Drinking games in college tend to get pretty athletic, and no one looks their best while pounding beers. However, there’s no reason to get soccer shorts and Crocs involved. You know things aren’t great when the only way you can defend your sartorial choices is by reminding people them that Mario Batali and Violet Affleck wear them, too.

The Recommendation: Let’s get down to brass tacks here. Sure, your outfit should be washable, and it should allow for optimal movement. Most importantly, though, it needs to clearly establish your Flip Cup dominance to everyone else at the party. Next time you’re lining up at the keg, opt for straight leg jeans, cute sneakers, and a comfortable V-neck.

J. Crew Ankle Stretch Toothpick Garment Dyed Twill Jeans, $49.99, available at J. Crew; BE & D Brightlight High Top Sneakers, $128, available at Shopbop; rag & bone Maya Top, $115, available at La Garconne.
2 of 5
The Scenario: The fact that your ex and his family are going to be at your friend’s wedding means one thing: You need to look fantastic. Unfortunately, your dress is too short, and you spent more time making sure your upper thighs didn’t stick to the pew than chatting up his mom.

The Recommendation: Next time, wear a nude-colored dress and keep the cut in the space between work wear and night-out garb. When your ex spots you from across the room, he'll regret that you two ever parted ways.

Acne Marlow Dress, $366, available at Seasons Clothing; Hoss Intropia Black Sequin Necklace, $200, available at Stylebop; Zara Tricolour Sandal, $79.90, available at Zara.
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3 of 5
The Scenario: You’re traveling and want to be comfortable while sightseeing (i.e., figuring out when Peru does la hora feliz). Last time we checked, they didn’t make a sequel called Sisterhood of the Traveling Sweatpants.

The Recommendation: While we get that comfort is a number-one priority when you’re far from home, it's hard to look stop-traffic stylish in sweatpants. Lucky for us, retailers have finally read our strongly worded letters and now offer comfy-chic pants that don’t require a juice cleanse and a pair of pliers to fit in. Our tourist look includes a pair of silky, loose, printed trousers.

A.L.C. Franco Pant, $395, available at Barneys; J. Crew Optic Dot Boatneck Tee, $45, available at J. Crew; ASOS Leather Slash Detail Duffel Bag, $129.35, available at ASOS.
4 of 5
The Scenario: Seeing live music at a bar calls for something casual and cute, not the sleeveless button-down and ribbon belt you would wear for a weekend of golf.

The Recommendation: We love animals, but we’d rather see them on YouTube than embroidered on our clothing. A loose-fitting, cotton tank and a flowy skirt will look great on the dance floor.

Topshop Faded Rose Print Dip Skirt, $76, available at Topshop; Splendid Vintage Whisper Cotton Slub Jersey Tank, $58, available at Net-a-Porter.
5 of 5
The Scenario: You managed to get out of bed, clothe yourself, and survive a post-bar hopping brunch. Respect. Unfortunately, that hoodie isn’t hiding your hangover.

The Recommendation: Our favorite brunch look is a loose, printed dress and a cardigan. The cardigan helps keep you cozy, the dress allows you to comfortably order an extra side of hash browns, and the print camouflages any Bloody Mary stains you might incur. It’s highly practical, unlike last night’s decision to enjoy six glasses of Champagne before dinner.

Mango Cascading Lapels Cardigan, $49.99, available at Mango; Steven Alan Flora Dress, $358, available at Steven Alan.
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