Skip to main content

Q: What Do I Wear to a Casual Bachelorette Weekend?

Every Friday we're taking your questions on all things style, beauty and business. Today's issue? Finding appropriate clothes for when you're throwing down whiskey shots in honor of the bride to be.

In our latest column, “Ask a Fashionista,” you can solicit our strongly held opinions on everything from how to wear a midi skirt without looking like a tree stump to whether a certain retail CEO should go ahead and resign already.

Q: My friend's bachelorette weekend is fast approaching and I'm getting a little worried about what to wear. I doubt anyone is going to get very dressed up at any point. (The bride to be has been wearing the same jeans almost every time I've seen her, and I've known her for nearly 3 years!). I need help figuring out what kind of outfits to pack! The weekend is probably going to be brunches, shopping and wild nights at dive-like bars. It really is a laid-back crowd, and I literally do not know how to "dress down" without looking like a slob. — Cassandra, Lexington, N.C.

A: The key here is to not overthink it -- everybody will be too drunk to notice what you're wearing!

But for real: if you don't like wearing jeans, don't buy a new pair just because your friend lives in them. For brunches and shopping, a sundress or t-shirt dress is totally appropriate with flat sandals or sneakers. My go-to store for sundresses is Madewell: they have a big selection and nothing feels too fancy. 

Scroll to Continue

Recommended Articles

In terms of sneakers, do you own a pair of slip-ons? If not, classic white Vans are a practical way to go. Personally, I lean toward lace-up Keds because they're a bit daintier. When it comes to sandals, there are tons of great flat, minimal styles in neutral colors available at pretty much every retailer. Lauren Indvik and I both love Gap's $39.95 version

As for those late nights in dive bars? Don't wear anything too precious. Drinks will be spilled on tops, shoes will be mucked up and who knows what bodily fluids will soil your outfit. Do yourself a favor and stick with black or navy. Reformation's "Dove" dress, $198, is easy and unpretentious. The open back is super sexy, but the flippy skater-style skirt brings it down to a level of normalcy. If you prefer separates, a pair of super-high waisted shorts and a sleeveless blouse make for a good look. I'm really into Everlane's silk tank, $55

Back to shoes. Again, since it's currently warm in most areas of the continental U.S., flat sandals are the best choice for evening too. If you must wear heels, go with something sturdy. You'll probably be bar hopping, and you don't want to hold the group back by being a slow walker. (Slow walkers are the worst.) 

And remember, it is a bachelorette weekend, so at least some of your fellow partiers will try to make an effort. It really is always better to be overdressed than underdressed. There is absolutely no reason to purposefully look like a bum. 

For more answers to life's fashion problems, click here. Have a question? Leave it in the comments below or send it to