What 10 Things NOT to Wear on Your First Date

Did you finally get that date with the guy you’ve been eyeing? Are you searching through your closet bewildered about what to wear? What to wear is easy to figure out, when you know what 10 things not to wear on your first date.

It’s that time again, ladies. That time of year when I decide to go out and date more. Maybe it’s my fear of dying alone that prompts me to get out and about, or maybe I’m just getting tired of lonely nights and an empty bed. Regardless of the reason, I’m going out on more first dates lately than ever before. Which means, I can tell you exactly what you should not wear on your first date (from trial and error) so that you don’t give off the wrong impression.

#1 See Through Tops

One of the most common articles of clothing women wear, and the most important of what 10 things not to wear on your first date, is the see through top. You could have the most beautiful breasts on the planet (and let’s face it, ladies, we have power with our breasts), but you shouldn’t let him see through your shirt on the first date. First, it leaves no mystery, and second, it’s tacky. Cover your girls up, ladies, and he can see them when you think he deserves to.

#2 Too Short Skirts


No matter how hot it is outside, there’s no reason to wear a micro-mini on a first date. This almost non-existent piece of clothing shows too much leg and too little inhibitions. By wearing a too short skirt on your date, you’re once again leaving very little to the imagination. A first date skirt should be no more than two inches above the knee. Classy, and it still shows off those toned calves of yours.

#3 Anything Unseasonal

No Christmas sweaters in July. No fur coats in June (unless you live on the North Pole). I shouldn’t have to tell you how ridiculous this looks, and trust me, he’ll think so, too.

#4 Loud Shirts

Unless you and your guy are going to a Luau, tone it down. One of the top 10 things not to wear on your first date is anything that will make your guy put on his sunglasses. If your shirt is neon green with neon flowers, you shouldn’t wear it. In fact, it’s outdated, just toss it.

#5 Too Much Make-up


We get nervous. When we get nervous, we apply too much eye make-up or too much lipstick. I get it, I used to be like that, too. Men are afraid to kiss women who wear too much make-up, they fear it’ll somehow leave your skin and transport itself onto his. Here’s the rule of three: Foundation, a touch of lip color, and mascara. Pinch your cheeks to make them pink, and that’s all you need.

#6 Unnaturally High Heels

There are two reasons why you should not wear unnaturally high heels on your first date. First, it looks trashy. I hate to use that word, but if you’re in anything above four inches on a first date, then you’re putting off a bad first impression. Second, walking is a necessity. I know you’re thinking “Of course I can walk in my stilettos’, I was born with these babies on!”, but you weren’t. If your date wants to take a stroll around town after dinner and you’re in six inch pumps, you’re going to be very uncomfortable by the time you get home.

#7 Red Nail Polish

Yes, it’s sexy. I used to only wear red nail polish, and I love the color! Still, it puts off a bad message. The reason you should not wear red nail polish on your date is because it screams “Vamp”. No, not sexy vampire woman…vamp. The woman who will rip his heart out and tear it to shreds, after she leaves his wallet high and dry.

I know, it’s silly to think that of a nail polish, but leave the red for date three.

#8 Fishnets


Unless you and your guy are on a Halloween date, then fishnet stockings are never, ever appropriate. I don’t even think these are appropriate for any date within the first three months. Here’s the thing, fishnet stockings are hot. They are super sexy and men go nuts over them (believe me, I know). But, they aren’t classy.

The main reason this is one of the 10 things not to wear on your first date is because fishnets scream sex, not class.

#9 Anything that Exposes too Much Flesh

If your date doesn’t have to think too hard to picture you naked, then you’re not wearing enough clothes. Lower the hemline, raise the neckline, and loosen the skirt. You have curves, and you have every right to show them off, just not by exposing yourself.

#10 Jeans and a T-Shirt

Finally, the last of the 10 things not to wear on your first date is jeans and a t-shirt. Now, I don’t mean nice jeans and a nice solid color t-shirt, that’s actually perfect date wear. What I mean is don’t wear those jeans that have holes all in them with a Guns ‘N Roses t-shirt you’ve been wearing since the 8th grade. Seriously, unless you’re going to a rock concert, this is not appropriate.

The thing to remember about first date wear is that you need to show that you’re a comfortable woman, and a classy woman. he has to actually listen to what you’re saying instead of eyeing your thighs all night. If your date can’t look you in the eyes because he’s too busy looking at your breasts, then you’re not on a date, you’re on a sex interview.

Wear casual and comfortable and leave something to his imagination. A pretty sun dress, form fitting blue jeans and a blouse, or even a flowing skirt and cute top are all appropriate. Oh, and no flip-flops! No.

What is your favorite first date wear? What do you think it's the most appropriate outfit for the first date?

About the author



Just another hard working mom who loves her kid, loves to write, can’t cook, and has a thing for tentacles! When I’m not hanging out with my Spawn, I’m happily sharing my dating experiences and offering advice and trying to control the chaos that comes with being human.


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  • Or how about you wear whatever you like and makes you feel good regardless of others opinions because your hemline doesn’t make you “trashy” and your heels don’t make you a criminal. It’s 2015, can we please stop judging everybody for every little thing?

  • A woman can wear whatever she wants to wear on a date, if a man deems it inappropriate and too sexual, that is his problem and should not be hers. Maybe you should focus less on telling women what they should not do and realise that this message is harmful and offensive. Whatever you wear will divide opinion so why not just wear whatever you feel most comfortable in and expresses you in the best way? There’s no need to judge women for their clothes and restrict them because their hemline might send out the wrong message to a judgmental potential partner.

  • Is this a joke? No red nails? What is this, 1924? Wear whatever you want and what’s comfortable.

  • Or you could wear whatever you want on your first date. If he gets himself in a state because he can’t handle what you’re wearing, and it’s your usual attire, and what you feel comfortable wearing, then he really shouldn’t be someone you want around anyway.

    You should go for a happy medium – comfortable, and attractive. And if that means that punk rock sh*t, ripped old jeans and shoddy chucks then that’s what you damn well wear! If that means you want to get dolled up and wear a short skirt with high heels, then do that! If it makes you comfortable, then that’s what matters. If you’re going too far away from your usual everyday clothes, then it’s not worth the effort! He should like you as you are.

    I get the whole modesty thing, and dressing for different occasions, but a first date isn’t outfit centered; and if it is… you have issues. Look good in the way you’re comfortable, but don’t let worry over what you’re wearing be the focal point. Sure, if you’re 15 and walk out of the house looking like a h*oker for a first date, this article is perfect; but that’s one for the parents to worry about.