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 past hometown fling, 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 on running into your ex—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.
What to pack when heading home for the holidays
While you might be tempted to just rely on the clothes your mom always reminds you you have at home, I can pretty much guarantee that you’ll feel a lot better about running into people from your past if you’re not in your old varsity soccer sweats.
When you’re packing to head home for the holidays, you’ll want to make sure your suitcase is stocked with easy and versatile pieces that make you feel confident as hell. You know, just in case you end up in that dreaded spotted-from-across-the-room-but-don’t-know-if-you-should-say-hi scenario with your ex. Even if you never actually dated, we know it’s still awkward (perhaps even more so). Here’s a short list of must-haves for spending some time at your parents’ house this holiday season:
- Two coats: one for fashion, one for function (bonus if your second option works for both, like the faux fur below)
- A nice pair of jeans (checks the boxes for both trousers and jeans)
- A comfy pair of jeans
- A sweat set, plus another comfy outfit (like a sweater and track pants)
- A few easy-to-throw on long-sleeve tops and sweaters
- A planned-out festive holiday outfit
- A tote bag, a shoulder bag, and a dressy bag if you’re feeling fancy
- Dressy boots, sneakers, and slip-on shoes
- Your favorite winter accessories
Below, I’m sharing outfit ideas for all of these pieces so that if you do run into your ex, you’ll leave the scenario thinking “Wow, I am so much hotter than them.”
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 monochrome jeans-and-a-cute-top combo with coordinating accessories.
Shop this look: Top | Bra | Trouser Jeans | Jacket (Plus) | Boots | Bag | Earrings
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 sneakers for ultimate cool girl energy.
Shop this look: Hoodie | Sweatpants | Coat | Sneakers | Beanie | Tote 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 striped sweater paired with sweatpant jeans, clogs, and topped off with a fun pair of earmuffs says, “I just stepped off the latest Netflix Christmas movie set.”
Shop this look: Sweater (Similar) | Sweatpant Jeans | Jacket (Plus) | Clogs | Bag | Earmuffs
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 an asymmetrical top, trouser jeans, and timeless accessories for a subtly sexy look that will make you want to run into an ex.
Shop this look: Top (Plus) | Trouser Jeans | Boots | Coat | Bag | Earrings
For a festive holiday party
There’s always some sort of holiday gathering or festive event to attend when you’re spending the holidays back home. If you want a truly show-stopping look, go for one of the season’s best color combos: plum and chartreuse. Paired with a sequin maxi, this look is sure to have heads turning (in the best way).
Shop this look: Sweater (Budget Option) | Skirt (Similar) | Alternate Skirt | Heels | Bag | Wine Bag | Earrings
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 sweater, cool sneakers, and a chic sherpa tote for all of your snacks.
Shop this look: Sweater (Plus) | Tee | Track Pants | Sneakers | Tote Bag | Glasses
Jessica Welsh, Senior Fashion & Beauty Editor
Jessica oversees and edits all fashion and beauty content on The Everygirl. She also writes in-depth styling stories, trend reports, capsule wardrobes, and more. She was previously the Commerce Editor for The Everymom, where she oversaw all shopping content on the site and social. She has created editorial content for major brands such as Nordstrom, Old Navy, DSW, and Kohl’s.
Products included in graphics linked within article. Feature graphic image credited to: Vittoria Tomassini | Dupe.
