The Classy Way To Go Topless This Season

As a girl with a silhouette shaped more like a shampoo bottle than an hourglass, a discernible lack of boobage, and a love for clothes that are big, baggy, and boyish, let's just say that "party clothes" and I don't really get along. I did the cocktail dress and high heels shuffle for years, but next to women who actually loved what they were wearing and how they looked in it, I always felt about as beautiful as a gingerbread man.

The alternative wasn't much better. My everyday arsenal of tomboy staples didn't really parlay into a logical "evening" look. So, I resorted to a few deliberate "look at me, I'm at a party" add-ons like red lipstick and a statement necklace to fool people (including myself) into thinking that I was dressed up.

And then I saw Jenna Lyons. She's always favored low-cut tops and barely buttoned oxfords worn with tomboy blazers and cardigans (save for a brief respite during the The Great Button-Up-All-The-Way Trend of 2011). And, recently, she's gone so far as to leave her top behind, going completely bare beneath a blazer. It's so cool, provocative, and sexy. With a similarly sized chest and frame, I looked towards Lyons' approach with optimism. I was going to go to a party and leave my shirt behind.

The first step was to find a blazer that was cut deep enough to really make a statement, and yet would lie flat enough that I could reasonably move around without flashing fellow partygoers. I borrowed a beautiful white Reiss blazer from our senior style editor Annie Georgia Greenberg that also came with a subtle sheen to it (extra festive!). On the bottom, I wore my go-to pair of black trousers and a fun pair of party oxfords. For a little bit more glamour (not to mention security), I chose to wear a long vintage pendant necklace.

The effect was nothing short of game-changing. As soon as I realized that I didn't need to be robot-stiff to remain covered, I danced, drank, hugged, and waved with abandon (I did, however, need to make sure I was standing up straight, which wasn't all that bad and would have made my mom happy). It was a conversation starter, but not a creep magnet, and the majority of the compliments I got that evening were from other women who recognized it as a Jenna Lyons signature. It was freeing, literally, to have finally found my thing.

So, to help fellow tomboys on their own journeys to faboosh, here are a few helpful hints for going topless this holiday season:

1. Take Care Of The Girls. If you have a difficult time going braless, this isn't the trend for you, although you can opt for a beautiful bustier or shelf bra to wear underneath a blazer. For women like me who consider bras a novelty, this look is made for you, and allows you to get your sexy on while still wearing a blazer. If you're worried about accidental flashing, some double-sided tape can keep you secure.

2. Up The Girly Elsewhere. Whether it's a swipe of lipstick, a long necklace, or a high heel, you need at least one additional element to really bring this look home.

3. Own It. Not wearing a shirt is probably not something you're used to. It's probably not something anyone is used to seeing. But, that's what makes it so fun to do. And, if you're approaching the world with confidence and excitement, it's going to set the tone for how you'll feel for the rest of the night.