Coffee-Date Dressing Is an Art Form—These 13 Outfits Nail It

You’re not alone if your first thought when tasked with picking an outfit for a first date is to panic. First, don’t (when there’s a will, there’s a way), but especially if you and your new prospect have a more relaxed meeting lined up, such as a coffee date, you probably already have more than a few tricks up your sleeve to creating a casual but cute outfit that will fit the bill. And if you don’t, we do.

Just as the first date is a means of easing into a something new with someone new, a coffee date doesn’t typically require getting glammed up to the nines (unless you want to!), and you can instead ease in with a more casual date outfit. Think the same kind of ensemble you may put together to meet a friend at brunch or for a solo date at a museum. For example, jeans with a standout top or a daytime dress made comfortable with flat shoes (you get the vibe). 

To get your gears turning, we found 13 potential winner looks that are all guaranteed to start your date off on the right note. Fingers crossed all pans out well, and perhaps you’ll be returning for a bit of dinner-date outfit inspiration next.

Pull out a top with a fun print to play the main character, with classic jeans and a sleek cowgirl-inspired boot to complement.

Black and white stripes paired with a pop of color always make for a chic look (just trust on this one). This time, try the combination with a lightweight sweater and a bright-red miniskirt. And because coffee dates call for no-fuss footwear, a pair of clogs.

A pair of leather pants and an everyday tank are about as simultaneously easy breezy and put together as it gets. Now is the perfect time to pull on the cozy quilted jacket you’ve been eyeing all season, too.

Any excuse to pull out the split-toe ballet flats. Let them become the star of the show by going simple and subdued up top.

This outfit has all the components of the ’80s done with a modern spin—a catsuit, bold shoulders, and a chain belt. Then, it’s the pointed-toe shoes that give the entire look a crisp finish.

Oftentimes, the best outfits for a coffee date are the coziest, especially this time of year. Reach for a chunky sweater and baggy pants. You might also try toying with pastels and color-blocking for added fun.

If you’re checking out a (hashtag aesthetic) coffee shop, perhaps bringing out the frills, such as a puff-sleeve crop top, is warranted. Feel free to keep it all nice and easy with jeans and trendy sneakers.

Denim on denim remains one of the biggest trends of the moment, but what about a two-toned take with a classic blue top and black jeans on the bottom? Then, add on a pair of square-toe cowgirl boots for a Western flair.

With attention to just a few key details, such as a perfectly flared leg and a leather blazer with just the right amount of boxiness, you can make a blazer-meets-jeans outfit look really posh. 

There is such a way to style a dress for a coffee date so that you don’t feel overdressed, such as adding a cardigan on top and opting for loafers over heels. 

How would the quintessential effortlessly cool L.A. girl do coffee-date attire, you ask? Obviously with a sleek trench over a chic cardigan and chunky sneakers to top it off. 

Daytime meetups make for just the occasion to try on the denim-midi-skirt trend. Go for a printed mesh top to add to the nostalgic vibe, with your choice of sandals or tall boots, depending on the weather. 

One key to simple but cute outfits is to mix pops of color with luxe texture. Think pairing the best black faux-leather pants with a bright green mock-neck. 

Next: 10 Easy Winter Outfit Ideas to Try at Work (and in Life)