4 years ago10,000+ Views
In this devastating modern age of hookup culture, bars, tinder, and texting, navigating the dating world is so hard! The worst thing is when you're supposed to hang out with someone and you have no idea if it's a date or not. Are you friends? Are you friends with benefits? Do they even know your last name? And then the most important question... what do you wear?
When you aren't sure if it's a date or not, you don't want to look like you tried to hard, and also don't want to look like a pile of garbage. What to do? I'll get you through it, I promise.

Don't wear: heels.

Unless you're a die-hard wearer of high heels 24/7, heels will send the message that you're dressing up and putting yourself through physical pain (you know it's true!) for this person. Don't do it. If you're trying to dress up your outfit, go for a cool pair of flats. If you want to dress down a dress or skirt, go for skater shoes in a polished black and white to look stylish, but also like you're not inconveniencing yourself. Flat sandals will do as well during these hotter months. Alexa Chung is queen of the flat; channel her tonight when you look for something comfy and casual but still flattering and pretty.
When you get the second date, then you can reconsider.

Do Wear: a denim miniskirt

If you want to show off some leg, denim is the way to go. It's on trend for this summer. and looks hot without being too precious or formal for a maybe-date. If the venue calls for dressed-up denim, throw a leather jacket on to carry it into night. Denim in anyway is an all-around good call on this uncertain of occasions, because it's classic, trendy, and can be sexy without looking too deliberate. The above look is great because the blouse gives the hip-hugging cut a polish, but the skater flats keep it super casual.

Don't Wear: a girly dress

Don't get me wrong; there is nothing wrong with embracing your femininity, and you can definitely communicate a strong, badass personality while wearing lace and ruffles. It's totally up to you. In this case, however, I'm going to steer you away from anything precious. A dress is a risk when you don't know the nature of the occasion. It can too easily be read as if you tried to make the "date" something it wasn't, and you don't want that. In case you're wondering, a semi-sheer maxi dress is not the look you're going for tonight. Jamie King looks adorable above, but we can all admit that that's a great outfit for a date that you're certain is a date.

Do Wear: skinny jeans in a cool color or wash.

Skinny jeans are a casual date go-to. If you want to be a bit more adventurous, opt for waxed denim or colored denim in a darker wash (which is more universally flattering than white or lightwash denim). Selena Gomez's waxed army-green pants look simultaneously cool and casual. The denim sneaker pairing is perfect; if you wear sneakers or skater shoes, a leather or faux-leather dresses it up while keeping with the laid-back vibe.

Maybe wear: a matching set

I'm writing this hesitantly, as you have to be careful with this option. It could go so wrong or so right. Matching sets can look girly and dressy, or cool and laid-back, depending on the cut and print. To be safe, go with a casual daytime-ready material (nothing silky or with a satin feel), and steer clear of voluminous skirts. But a matching top and shorts, or crop-top and culottes is super stylish and easy to put together. If you want to dress it down, tie a denim shirt around the waist. Dress it up with a leather jacket. Remember, no heels! Refer to this card for guidance.
Do: show a slip of midriff with your crop-top and bottoms set.
Don't: show so much of your stomach that you look club-ready. It'll mess with the casual vibe.

Do Wear: leather leggings

Kendall's slouchy white tee is the perfect casual complement to the dressed-up leggings. Worn with chic sandals or flats, you're a mix of day and night, sexed up and "I don't care" attitude. If you want something a little sexier, pick a white tee that's just the tiniest bit sheer and wear over a triangle bra or pretty bralet. The comfy cotton tee is exactly what you want, because it flatters your body without doing much work. Bonus points for the sleek ponytail.

Don't Wear: a boxy dress that hides your shape

Okay, so you don't know if this is a date, but do you want it to be? If you're interested in this person romantically, you'll want them to be thinking at least a little bit about your body, and how can they do that when it's entirely covered up? It doesn't have to be a bodycon dress (it probably shouldn't be) to skim over your curves or emphasize your waist a little. If one of your favorite dresses is fashion-forward but so boxy that you could technically be hiding a pregnant belly under it without them noticing, nix it for tonight.

Do Wear: a t-shirt dress

A t-shirt dress with short sleeves and a cool print is perfect for a casual night of flirting and possibly dating. The short skirt is just sexy enough, but a crew neck and loose fit keep it from looking like you tried to be a sex kitten. Selena's dress is perfectly casual and trendy. Her gladiator sandals dress it up just enough for an awkward maybe-date, maybe-not date situation. Wear yours with statement sandals for day, or booties and a leather jacket for night.

Above all: wear your go-to's

If this person knows you at all, they'll have a sense of what you usually wear. If this is a night at a bar, wear what you like to wear to the bar, just not what you'd wear to a DATE at a bar. If you're going to a game or a movie, stick with your wardrobe staples. Unless it goes against one of my no-no's above, if you like to wear it, wear it. It's visible when you're comfortable in your own skin, and equally visible when you're comfortable in your own clothes. Stick with what you love, what makes you feel good, and what you know you look good in, and you can't go wrong.
Happy maybe-dating and good luck out there! It's a dog-eat-dog world and we're stuck in it!
I am notorious for mistaking dates with 'just hanging out' so I'm usually dressed pretty casually haha I'm definitely a jeans and tshirt kind of girl :)
Definitely clipping this – I ALWAYS find myself in these kinds of situations. Maybe it's because in our generation, people are too scared to come right out and admit that they're into someone. So we tiptoe around dating and just "hang out" or "chill." But @gavriella you totally get me – the most important question totally IS what to wear ;D gotta always look your best so even if it isn't a date, he knows he's missing out!!
@LizArnone thanks! Yeah they're the perfect way look casual but be slightly more put-together than just a tee and shorts
I love this!! hahah i a super into this tshirt dress thing thats happening and i need to get about a million of them !
that's good, @caricakes! Most girls I know would say the opposite, that they're notorious for mistaking "just hanging out" for a date
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