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Date Night Dilemmas – What Not to Wear on a Date

what to wear on a date

You’re headed out for a date, but you have no idea what to wear. While you can wear whatever you want, here are some items to avoid.

Few things are more boggling than looking into your closet in order to find the perfect outfit for a date. Oftentimes, the clothes you wear on a date also subtly convey who you are and what you want out of the date. And that’s why many women put a lot of thought into what they’ll be wearing.

What’s the message you want to convey? Would you like to show him that you’re fun, hip and casual, but not so much that you look like you don’t care about your appearance? Do you want to appear sophisticated and classy? Do you want to look like a low maintenance gal who has great enough taste to pull off something so laid back?

With all these things that come into your mind as you prepare for your date, it’s very easy to go over the top. That’s why we’ve compiled a list of stuff that you probably shouldn’t be wearing on your date, unless you want him to start running the other way. [Read: Your best clothing options on a first date]

What you should and shouldn’t wear on a date

And unlike many other sites that tell you what not to wear, we’ve also included some alternatives for what might be a better option.

#1 No to sportswear. Okay, so you’re an athlete. That’s pretty cool. But looking like you just got out of the gym wouldn’t be very appealing to your date. Yes, it shows your date that you’re a fitness fan, but it also shows that you can’t be bothered to wear something nice when you’re going out with someone. Besides, wouldn’t it be better if he found out that you’re a fitness buff by seeing that you’ve got a toned physique?

Yes to casual wear. Gym clothes are very comfortable, that’s true. But there are a ton of other clothes that are just as comfy as gym clothes. For instance, you can wear a lightweight cotton shirt with a pair of jeans and flats. You don’t always have to give up fashion for comfort!

#2 No to uncomfortable footwear. What’s worse than wobbling around while you go for a walk with your date? Not only will you be more prone to embarrassing and potentially painful accidents, but you might go home with a tiny colony of blisters on your feet. Yes, those sky-high stilettos and ankle-breaking wedges might look great with your dress, but aren’t there other options like…

Yes to comfy yet fashionable shoes. There’s a reason you’re allowed to try on shoes before buying them: so that you can get to choose the pair that are comfortable to walk in. Instead of shoes that stretch your arch to its limit, go for shoes that have soft insoles. Instead of going for heels despite your distaste for them, opt for cute flats or a similar style with lower heels. Your feet will thank you for them.

#3 No to super short… anything! You want to show off your super long and super toned legs, so you choose to go for a short dress or skirt that barely covers your unmentionables. It may look good when you’re posing in front of your mirror, but the problem is that you might end up exposing yourself when you move around. Just imagine trying to slink down off a bar stool in a super short skirt! And don’t get us started on wearing a flowy short skirt on a windy day! [Read: Revealing clothes won’t do you any good in the workplace, either]

Yes to tights with short skirts and dresses. Zooey Deschanel knew exactly what she was doing when she showed up on the big screen as the opposite of your typical hot vixen. Her fashion style revolves mainly around feminine wear with the added touch of black or navy tights. Tights let you show off how toned your legs are without showing the world what’s going on beneath that skirt. It’s the perfect balance of sexy and feminine! [Read: 15 super simple ways to stay sexy at any age]

#4 No to flashy, glittery clothes. You’re already out on a date with someone you could potentially hit it off with. So there’s really no point in wearing something as attention grabbing as a dress bedecked in jewels, sequins and glitter. You wouldn’t want your date to take one look at you and instantly become blind, would you? Flashy and glittery clothes are better off worn into a club or at a rave, and not at a quiet little restaurant with your date.

Yes to accessories. If you’re the type of girl who loves to get her glam on, you can still do it in a more tasteful way. Keep your outfit relatively simple and stylish, but adorn it with key pieces. Examples of these key pieces are a chunky necklace, dangling earrings or a bejeweled cuff. They’re not too flashy, but they’re still eye catching and appealing.

#5 No to anything that needs double sided tape. You’re on a date, not a red carpet movie premiere! It’s best to save those outfits for another occasion, particularly one where you get your own personal assistant to watch out for clothing mishaps. Besides, anything that requires double sided tape is just begging for a wardrobe malfunction!

Yes to mesh dresses. If you really, truly want to show off some skin, your safest bet is a top or dress with mesh cutouts. They’ll still remain intact, even if you move around, but the mesh allows you to show off your bod. Though this isn’t exactly the most tasteful outfit for a date, it still beats out anything that an errant gust of wind might blow off you.

#6 No to a ton of hairspray. We know how important it is to keep your hair in place, but making your hair as hard as a helmet may not be the way to go. Not only is a lot of hairspray bad for your hair, but it can also be tough to get rid of in the shower.

Yes to a simple bun or au naturale. You’re not aiming to look like you’re in a photo shoot, so why all the fuss about keeping all your hair in place? Instead of the very 1960’s look of hairspray-drenched styles, go for a low and slightly messy bun. The tendrils that frame your face can actually be very flattering, and it gives you a very romantic vibe. Perfect for a date!

#7 No to a whole array of trends. A peplum dress with mesh on the sides with trendy Louboutins, topped off with ombre hair and a denim jacket… It’s a fashion train wreck! We know that the latest trends may make you feel hip and “in,” but jamming a hundred looks into one outfit just won’t cut it. It may look great on a model in an editorial spread, but the things you see in editorial shoots don’t translate that well in real life. Your date might just be confused with so many things going on in your outfit!

Yes to the classics. Classic clothes never go out of style. The reason so many trends are in place is because the fashion industry is always looking to market the next big thing. But you don’t always have to follow these trends. Just go for clothes that feel good and look good on you. It’s much better than following trends that are neither comfy, nor flattering. Trust us when we say that men aren’t too keen on the latest trends, so they’re more likely to notice clothes that look great on you instead of the latest thing Kim Kardashian is wearing.

[Read: 16 first date tips to dazzle your date]

Skip skimming through beauty magazines for the latest styles, and just go with what looks and feels good on you. Your date will definitely be the first one to notice when you’re wearing uncomfortable clothes in an attempt to look sexier. Just relax and make your confidence your best accessory!

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3 thoughts on “Date Night Dilemmas – What Not to Wear on a Date”

  1. Hunny says:

    These days it is easy to be fashionable and comfortable at the same time. Wearing frumpy clothing or ill fitting things are not good choices. I love wearing things that match my style and preference but still be sexy. That can even mean jeans if they fit right and are paired with some cute top and shoes. Wearing gym clothes is a no no and ugly shoes are a turn-off as well. If you have your own personal style then use it to be date ready, appropriate, and appealing to the eyes.

  2. brigette says:

    Oh please, do not, I repeat, DO NOT wear skimpy clothes on a date. Especially on your first date! It’s just an invitation to the guy to go have sex with you on the first date. It’s not okay to wear really short revealing clothes when you’re trying to get to know someone because it is so distracting to men. Not just the man you’re dating but all the other men in the restaurant. Men have peanut brains so they can not process a lot of things at once. Your date will only be focusing on what you’re wearing and what’s underneath it.

  3. Gayboy says:

    Dress, nice shoes, nothing overly elaborate but something that suggests a degree of effort. Naturally it depends on what you’re doing. Going for coffee might not warrant your best dress and heels. But if you are going to a fancy place, I always tell my woman friends this, the classic little black dress never fails. Heels not so high that they hurt, go simple and sparing on the accessories and makeup, but absolutely make those eyes stand out.

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