How to Dress for a First Date

By on May 1, 2015

When you feel the anticipation of going out on a first date, you might feel excitement, or maybe high levels of anxiety. The usual “what if I spill my food in my lap” or “what if I wear high heels and fall down” or “what if I can’t find something to talk about and he thinks I’m a total idiot?!”.
All the usual worries and fears that come with a first date are part of the butterflies that make it so exciting to actually go through with it. The risk/reward ratio of a first date is part of the appeal, “what if he’s the one!” or maybe you aren’t even looking for Mr. Right Forever, but just Mr. Right Now.
You may feel a panic when you go to your wardrobe and look inside, but don’t worry; you probably have something in there that works. Just take a deep breath and start pulling out things that fit you comfortably, that you can dress up or down as needed.
A date is not where you want to wear an outrageous, attention getting outfits. If you want to dress like Nikki Minaj or Lady Gaga save it for some other time. A first date is not an ideal way to show off your outlandish styles.
Here are a few things to consider for your first date before choosing your outfit. As this has a huge part in choosing what to wear.

  1. Be neat.
Victoria Beckham

Victoria Beckham

You don’t always need to go buy a brand new outfit for a first date, but make sure whatever you choose to wear is clean, and isn’t wrinkled like it was stuffed in the back of your drawer and you just threw it on without even bothering to de-wrinkle it. Check for stains, tears, rips, or seams coming apart before you wear it in public. While you may not care or notice, it may make him think you are a slob, or very inattentive to your own personal hygiene.

  1. Know your environment.


Know where you are going. This is important because if you don’t know where you are going, you won’t know how to dress for the situation and over/under dressing can make the situation feel more awkward than it needs to be. You might not want to wear those sexy heels that are hard to walk in, or hurt your feet, if you are walking around before or after your dinner date. If it’s cold and you don’t want to bring a heavy jacket, you may change the type of dress you plan on wearing if you might be standing in line, or waiting outside before dinner.

  1. Dress comfortably.
 Oliva Palermo

Oliva Palermo

First and foremost, you want to feel as comfortable as you can on a first date so you can focus on the more important things, like getting to know the person you are with, instead of trying to un-wedge a too tight skirt and pull it down the whole night. If you are fidgety, he’ll either think you are high maintenance, or bored. Neither are the impressions you want to give on a first date. Don’t wear clothing that doesn’t fit, or is too tight or barely covers your nipples, if you are constantly re-adjusting your clothes, or trying to keep your large breasts inside a too-small top, it’s just not the right message to send on a first date.

  1. Be yourself.
Blake Lively

Blake Lively

Whatever you choose to wear, be true to yourself. If you are tall, and not comfortable in extreme high-heel shoes, wear flats, or pair some Keds or Converse shoes with a sexy, but stylish outfit instead. If you are heavier set, wear clothing that shows off your curves without being skin tight – and tight and skimpy doesn’t always send the right impression on a first date, even if you can pull it off. Try dressing a little classier so they actually focus on getting to know you in return, instead of wondering what your boobs look like under your tube top.

  1. Stay classy.
Kate Middleton

Kate Middleton

Classy dresses are always a good option. You can always dress up or down a little black dress, and it suits most venues, however, if you are going to the beach, or a brewery, you might want to dress down just a tad so you don’t feel like you’re the only person there who’s not wearing jeans and a t-shirt. You can still wear a dress, but you may pick something lacey, or with flowers instead. Or instead of jeans, wear a jean skirt, with some high heeled sandals and a cute halter top with a light sweater.

  1. Go easy on your makeup.
Amanda Seyfried

Amanda Seyfried

Makeup and hair is also an important part of a first date. You don’t want to overdo it, or under do it, you want him to think you spent time on your appearance, but didn’t make yourself look like a painted doll, especially if that’s not your normal makeup routine. Most men like subtle makeup that accentuates features, if you put it on with a heavy hand, they may worry they’ll end up wearing your makeup instead of you, because it’s that caked on. You want them to be thinking about kissing your soft, feminine mouth, not wondering if they’ll wear your lipstick on their teeth.

  1. Respect your date.


If you never wear makeup, a little colored lip-gloss or mascara and some moisturizer won’t hurt; put some effort into it. It makes a man feel appreciated, even if you don’t like wearing cover-up and/or blush and spending hours figuring out which color of nude or beige lipstick to wear. If you don’t feel bothered to dress up for him, the message you are sending is “what’s the point of this” or “this isn’t important to me” – be excited. Show that via your outfit, and makeup routine, and that you spent some effort getting ready to go on this first date with him. He’ll appreciate it.

  1. Draw attention.
Cara Delevigne

Cara Delevigne

Pick a feature on your face that you want to draw the most attention too – and use that as your starting point. If you have nice full lips, red lipstick works well if you know which shade of red suits you, but don’t over-do your eyes or you’ll look like a painted clown, and the same goes for if you draw more attention to your eyes, leave the rest plain.

  1. Don’t forget your nails.


Don’t go overboard on a crazy manicure right before a first date. Neat, trim nails, with a solid color or clear coat looks great. Men who notice nothing but glitter on your nails, may find it distracting and take away from the rest of your outfit or the conversation if they are busy watching your nail gems sparkle away. Your nails should never be the center of attention on your date.

Lastly, there’s tons of advice on do’s and don’ts out there for first date tips. The key here is dress to be comfortable, classy, and let yourself be able to shine, so you can get to know each other instead of focusing on the missing button of your shirt, that you have lipstick on your teeth, that your stockings have holes in them, or that you look like you just left a funeral, instead of going on a first date.
Effort matters, but remember to dress for where you are going so you don’t stick out like a sore thumb either.


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