Why is it that we are experts on creating looks on a daily basis, but when it comes to first dates (and dates in general) we freeze? Sure, first dates are all kinds of tricky—from scheduling the ideal time and location to acting as if you haven't already casually stalked your date on Instagram—but our outfits shouldn't create such a fuss. They should come naturally because nothing exudes more confidence than an outfit that feels inherently you.
We’re no dating experts, per se, but we strongly believe that you can't go wrong with a coffee date, somewhere you can actually sit down, talk to your date, and get to know them. Plus, if things get awkward, you can just casually people-watch. But, in the context of this story at least, the biggest plus about coffee shops is that they don't have a strict dress code. No matter the season, you can show off your personal style in a cute and casual way without feeling any pressure to overdo it. Phew, right?
Of course, if you have a date around the corner and still feel like you need a good dose of outfit inspiration, you know we're here for you. Below, behold 15 winter coffee-date outfits that are the right amount of cute and cozy. From dressing up your sweatshirts with skirts to expertly styling oversize sweaters and pants, these outfits will do just the trick.
You can't go wrong with a monochrome outfit.
Dress up your jeans with a playful coat and bold boots.
A long-sleeve maxi dress makes for an effortlessly stylish outfit.
Play around with pastel colors. You won't regret it.
Take your favorite midi skirt for a spin and style it with suede over-the-knee boots.
Don't forget to layer up with a coat!
Make a great first impression by showing up in a color-block look.
Chic but casual.
Doesn't get cozier than this.
Cropped pants are a cool and casual choice to pair with a bold, chunky knit sweater.
Corduroy pants were made to be worn in coffee shops.
If you want to go for the classic sweater-and-pants combo, punch things up with striking color blocking.
Show off your personal style by styling your dress over your pants.
Elevate your hoodie with a pair of silk trousers.
When in doubt, choose your leather jacket.
If it's a bowling date you're worried about, we have a few outfit options for that, too.
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