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In my book, summer is the flirtiest season. Let me explain! There's just something about the heat that makes you feel like anything could happen—and there's the fact that everyone's showing a little extra skin too. Another plus is that there are simply so many activities to do for dates. Whether you're just testing the waters with someone on Hinge, you're going steady, or you're locked down for life, there are so many summer dates you can plan. But after the plan is set, the question always remains: What do I wear? And the answer is any of these 28 summer date outfits.
Before we dive into the looks, let's talk strategy. The key to summer date dressing is fabric choice—lean toward lightweight materials like linen and cotton for everything from breezy summer dresses to sleeveless tops, and you can avoid embarrassing pit stains. Don't underestimate summer nights either. Though temperatures can be scorching during the day, it's always smart to bring layers if you know you'll be out late. Plus, every place cranks their air conditioning units, so lightweight cardigans and sweatshirts will keep you from shivering indoors.
With that covered, here's your mix of dressy, cute, and casual options to handle whatever the day or night has in store. From movie theater dates and coffee hangs to fancy dinner spots and cocktail bars, these outfits have you covered.
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Sometimes it doesn't matter what the activity is. If you know it's going to be H-O-T outside, opt for some mini shorts, a cropped tee, and simple flats for sandals.
There's nothing like a farmer's market to help you reset over the weekend. Shop the fresh produce, grab a bite to eat, and shop for some flowers while looking cute in this gingham number.
Rooftop season is the best season. Head to the top floor of your favorite spot in this black strapless top with dainty ties. Complete the look with light-wash jeans so it doesn't look like you tried too hard, and throw on some black sandals or heels to finish it off.
You can never go wrong in denim and denim. If it's the first date and you've planned a casual coffee hang to feel things out, opt for this smocked top, denim shorts, sandals, and a shoulder bag. You'll look pulled together in an outfit that fits the vibe.
If you've planned to walk a nearby boardwalk and check out the sights and rides, this loose dress, sandals, and a straw bag are perfect. It won't restrict your movement when you need to show off your carnival-game skills.
A dinner on the water brings allll the romance vibes. Match the beach scenery in a tropical matching set, sandals, and a clutch to strike the perfect balance of ease and elegance.
If you have a feeling the night won't end after your dinner plans, get yourself a going-out top that's comfortable, easy jeans, and not-too-high heels.
Recreational Habits Kennedy Short Sleeve Polo in White
So they're sporty, huh? And so are you! Dominate the court in this preppy all-white polo and skirt set.
For the days when you don't want to leave your home's air conditioning, this set is cute for a movie night in at your place... or theirs.
An Aperol spritz would go SO well with this breezy striped top, jeans, and metallic slides.
Head-to-toe white is the way to go to keep cool outside if you're heading to a park. The elastic waistband and stretch of this top will keep things comfy, while you keep things dressy with black contrasting accessories.
Spend a cultured day together and take in the art with an outfit that's just as much of a masterpiece. For a day on your feet, go with loafers and crew socks, then throw on this lightweight cotton top and shorts to complete the 'fit.
A road trip is a great date idea if you love to explore and find new places. If there's a longer car ride involved, comfort is key with a loose maxi skirt, sandals, and a simple white tank. Bring a larger shoulder bag in case you buy one (or five) new things on your journey.
A night out can mean a lot of things, but usually it involves dinner, drinks, dancing, and walking. Go for an outfit that is polished enough for a restaurant, but also works for bar hopping with comfy sandals, trendy capris, and a sheer off-the-shoulder top.
Go team! Whether it's basketball, baseball, or hockey, a white tee and jeans are a great base to start with. Throw on a baseball cap (bonus points if it's repping the team colors!) and sandals or sneakers to look effortless but also semi-sporty.
Beach days are looong so come prepared with a big-ass bag that can fit your book, towel, sunscreen, and maybe a change of clothes. Throw on a button-down and printed shorts over a bathing suit, and you're all set for a fun day spent in the sun.
If your summer is filled with weddings like mine is, impress your plus one with a bold maxi dress that works for both formal and casual weddings. A silver bag and black heels are accessories you'll wear over and over again.
A mesh top and denim mini are the perfect combo for a concert date. Wear strappy heels or low-key sneakers, then complete it with a colorful shoulder bag.
You bonded over books, so now you're heading to your local bookstore to pick some out together. Awww, cute! This coordinating set with bows in the front will definitely turn heads, but it's also subdued with its denim material. The best of both worlds.
Cooler is full, blanket is packed, your spot in the park is picked out. All you need to do is wear this red gingham dress with ruching on the side to complete your picnic day. A woven bag and espadrille shoes complement the look.
I'm Cosmopolitan's Associate Fashion Editor and write about any and all trends, major celeb fashion moments, and why wide-leg jeans are basically the best. I originally moved to New York City to audition for RENT, only to find out that the play closed 10 years ago.
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