There’s a reason sweaters are the unsung heroes of cold-weather dressing—they’re cozy, flattering, and endlessly versatile. But when it comes to date nights, finding the balance between snug and sophisticated can be a tricky dance (and lead to a pile of clothes on my couch with no idea of what I should wear). No one wants to show up to a date looking like they spent the day in bed, but shivering while wearing a barely there top isn’t exactly the vibe either. That’s why when my friends ask me what they should wear on a date night, I tell them that my formula hasn’t changed—cute jeans and an even cuter sweater.
I’ve rounded up a list of 31 sweaters that make dressing for date night a breeze, whether you’re braving the cold for rooftop cocktails or keeping it casual with dinner at your neighborhood favorite. These styles offer just the right mix of effortless chic and stay-warm practicality, so you can focus on the fun part—making memories. All you have to do now is add your favorite jeans.
A fun way to show up to the date and make them question whether you’re wearing a jacket or a cardigan.
The cinched waist here is a winner.
If you’re in a warmer climate but still want to give cozy, this is the vibe.
I’m obsessed with this.
This with layered necklaces is a shoe-in.
The lace is a very alluring detail.
I would add a gold bracelet to the sleeves for a fun bubble effect.
Because texture is trending.
This is so chic.
A pop of color will make your skin glow.
I love being preppy on a date.
This is barely considered a sweater, but I’m obsessed with it.
I want this entire outfit for my next date.
Sometimes wearing a subtle logo is a good idea.
There’s a ’90s vibe about this that’s fun.
This is an eye-catching design.
I’m still here for a bright-red moment.
Not your grandmother’s pearls.
The piercing detailing on this sweater is so fun.
For a more daytime vibe.
Obsessed with this.
The perfect matching set to wear if that’s your vibe.
Inspire your date to give you flowers with this sweater.
If you wear a crop top, this one is effortless and cozy.
All about this sheer and stretchy vibe.
Oversize always makes for a cute outfit.
We love a two-in-one deal.
I always tell my friends to try something off-the-shoulder for a date.
Something about this has sold me.
This is a really pretty take on burgundy.
Incredible.
