Dates: Where to go and What to Wear

If you clicked on this article, chances are you’re single and ready to mingle. Or maybe you’re already mingling with a certain someone, and you’re prepared to take it to the next step and go on some dates. With states and their establishments slowly reopening, it’s time to take your dates off socials and into the real world.

I’ll admit it — first dates are scary! Will they like you? What if it’s awkward? What will you guys do, and where do you go? And most importantly, what do I wear?! If these are the questions milling around in your head before you answer their “wanna do something?” text, you’ve come to the right place. 

Welcome to this article, I’ll be your sommelier this evening, recommending the perfect date-to-outfit pairings. Let’s get into it.

Visit Museums

The first date idea would be going to a museum. Almost every city has one, and if yours doesn’t, there is most definitely one only a car or train ride away. Even if you’re not familiar with artists or go to museums often, this is the perfect place for a first date. There is so much to look at and explore, which sprouts a slew of different conversation starters. A bonus is that, in my opinion, the way people perceive art and how they interpret it says a lot about their personality and their view on the world. This way, you get to delve a lot deeper than you would on your average dinner date.

Most museums and art exhibits are pretty decent in size, so my main outfit tip for this dating genre is to wear comfortable shoes. Sneakers, mules, or a block heel would be the best choice. For clothing options, choose dark or neutral tones, to not distract from the art on the walls. Lastly, top it off with a beret for an added artist effect.

Wine & Paint

Wine and paint is arguably the simplest date idea, but it’s also thoughtful and beyond cute. I’m sure many of you have heard of the classes you can sign up for where they give you a painting prompt, a glass of wine, some brushes, and tell you to have at it. Well, you can make a class right at home! You and your counterpart can choose a painting, have some wine, and maybe a charcuterie board. In the worst-case scenario of a bad date, you still got a cute painting out of it, right?

An outfit for this date should be casual, comfy, and ready to get paint on it. I suggest a pair of jeans; they’re easy to throw in the wash if you get paint on them! My favorite summer jean garment is your classic overall. It’s easy to throw on over anything, and it gives you the cute ‘painter aesthetic.’ Because overalls take up most of your outfit, focus on the accessories. I love a good headwrap or headband to keep your hair back while painting, some cute platform sneakers to elevate the look, and some clear glasses for a complete artistic look.

Arcade Games

If you’re competitive, you may want to stay home instead of this date idea. Arcade games are insanely fun, usually affordable, and if you’re at the right place, you’ll get an overpriced stuffed animal afterward as a keepsake. The two-player games will give you some insight into how you work together as a team, or maybe the competition will ruin the whole thing. Either way, it’s lots of fun, memorable, and you can do so many things at one location.

Not to be outshined by the neon lights, flashing games, and loud ringers, spice up your outfit for this date. I love the idea of a retro arcade arena, like the one you’ve seen in Stranger Things, so hone in on the flare that is the 70s. Loud and fun pants or jumpsuits is the way to go. Pick something that’s not too tight or short, so it makes it easy to slide in and out of racing games, bar stools, and (if your counterpart is lucky) a very charismatic photo booth. If you’re going to wear heels, pick a block heel for maximum support and comfort, as there will probably be a lot of walking, and maybe hopping on the Jumping Jackpot game. Pick a top and accessories that complement your look without taking away from your fabulous flares.

Picnic in the Park

Arguably the most romantic and down-to-earth date options, a picnic is the perfect lunch date at a low cost. Whether it be at a beach or Central Park, all you need is a handy-dandy picnic basket, snacks, and a blanket or sheet for lounging. I also recommend some bug spray, as I’ve seen way too many childhood story traumas of ants taking a residency on your picnic and in your pants.

This type of date is excellent for florals, ruffles, and anything flowy. Think long walks on the beach with the wind wisping your dress’s train behind you. I recommend a full length or a midi dress for this occasion, as sitting down in a tight micro dress or mini skirt isn’t the most flattering or comfortable. Wear sandals that are easy to walk in uneven surfaces and easy to take off and put on to ensure the majority of your time is spent with your date and not with your shoe buckles. Complete this look with feminine accessories—bandanas or sun hats for the hair and dainty jewelry for necklaces and earrings.

The Movies

Last, but not least is the classic movie date. If your local movie theaters aren’t open, this is also something that can be easily created right in the comfort of your own home. However, be sure to talk to your date on what kinds of movies they like and what they want to see because nothing is worse than hating scary movies and being stuck in one for over an hour. That would make for a horror movie of a date.

There are two ways you can go about movie theater outfits. I love the comfy look where I can put my feet up, snuggle into a hoodie, and munch comfortably on popcorn. For this aesthetic, your favorite hoodie will suffice or look with more depth, favorite tee, and a cozy zip up. Either way, you’ll want to bring a jacket because, for some reason, global warming doesn’t exist in movie theaters. Or, maybe you want to freeze so your date will feel obligated to put his/her arm around you to keep you warm. You sly dog!

The second way you can go to the movies is by going to the cinema. And by that, I mean going all out – blazers, dresses, pantsuits, and a dolled-up hair to match. I would reserve this upscale look for a dinner-then-a-movie date where you want to look nice.




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