"While the holiday season comes with a long list of things that we adore, it also comes with a few things that are not so fun. For example: dealing with comments from your problematic uncle at family dinner, having trouble with budgeting, and running into your hometown ex, just to name a few. Although all of those things might be a little uncomfortable, they don’t have to be unbearable. No promises on dealing with your uncle, but we can at least help you the last one—in the form of some outfit ideas.
Unless you’re a fire sign who lives for a little bit of drama (no shame!) or are still friends with your ex, you might dread the thought of running into them while visiting home for the holidays. And hey, even if you are on good terms, you still want to look good and feel confident if this happens. From grabbing drinks at your hometown bar to doing some holiday shopping, we’ve got outfit ideas for any occasion in which you might run into your ex.
For hitting up your local bar…
Ah, the local hometown bar scene. Even if you say you hate it, you’ll probably find yourself being dragged there at least once by your high school besties. You’ll want to look cute and feel confident—but also not overdo it. The answer? A flattering bodysuit, a cool pair of jeans, and a black jacket.
bodysuit (plus) | jeans (plus) | jacket (plus) | booties | bag
For the last-minute grocery run your parents send you on…
We all know this grocery run: It’s the eleventh hour, the grocery store is the most packed you’ve ever seen it, and you always (ALWAYS) see someone that you know. Don’t be caught in your ratty old high school sweats this time. Instead, throw on a matching set with a coordinating beanie and Ugg slippers for ultimate cool girl energy.
hoodie (plus) | sweatpants (plus) | jacket (plus) | beanie | slippers
For a nice dinner out…
Whether you’re going to your favorite local dinner spot with a group of friends or with your family, it’s the perfect time to bring a little city-girl-chic to your hometown. Opt for a satin blouse, trousers, and timeless accessories for a subtly sexy look that will make you want to run into an ex.
blouse (plus) | trousers | coat | heels | bag
For a festive holiday activity…
There’s always some sort of play, show, concert, or market to attend when you’re spending the holidays back home. You truly can’t go wrong with a tweed jacket, skirt, tights, and boots combo—and you’ll feel confident in the case of running into any exes.
sweater | turtleneck | skirt (plus) | tights | boots | hair bow | bag
For holiday shopping…
There’s a theory that wearing bright color makes people more attracted to you (OK fine, a theory I saw on Tiktok). Regardless of whether that’s true, why not lean into it with this effortlessly cool look? A green sweater paired with relaxed jeans, a long coat, Uggs, and topped off with a chunky scarf says, “I just stepped out of a Pinterest board.”
sweater (plus) | jeans (plus) | coat (plus) | scarf | Uggs
For going to the movie theater…
For some reason, I tend to wear my least flattering outfits whenever I’m heading to see a movie in theaters. But knowing how common it is to see movies around the holidays, I can’t be caught off guard this time around. Swap your sweats with a cozy cardigan, cool sneakers, and a chic sherpa tote for all of your snacks.
cardigan | leggings (plus) | puffer coat (plus) | tote | sneakers