11 Style Mistakes To Avoid On A First Date

11 Style Mistakes To Avoid On A First Date


July 10 2014

Chris Hondros/Getty Images News/Getty Images

Apart from the first day of high school, getting your first speeding ticket, and waiting to hear back from that dream job you applied for, there are few things in life that can make your palms sweat more than a first date.

What if he or she is weird? What if we run out of things to talk about? What should I order? What shouldn’t I order?

Since you can’t prepare for most of those scenarios ahead of time, try to stop thinking about all of the things that could go wrong. Trust me, it’s not worth the energy.

One thing that you can, however, control is what you wear on the date—and I’m definitely not going to judge you for stressing out over this. I get it. You want to make a good first impression, which is totally reasonable. My biggest fear was always choosing the right shoes to wear. I’m 6’2”, so (at least in my mind) my challenge was to find a pair of flats that were as sexy as the sky-high heels that the women around me were wearing. I finally realized that I was probably more comfortable in flats, anyway. That made it easier for me to relax and just be myself, which is what’s really important.

In terms of what to wear on a first date, there are so many “rules” floating around that it can be hard to parse out the good from the not-so-good. In the end, it’s all about what makes you feel like the best version of yourself. That being said, there are a handful of tried-and-true tips that are applicable for most women in almost any first date scenario. Below are 11 of them, as told by a mix of relationship, dating, and style experts.

1. Wearing Something Out Of Your Hamper

Your best bet for a first date outfit probably isn’t that pair of jeans that you’ve been wearing all week. Chances are that they’re all stretched out and have maybe even collected a few stains. Instead, wear something fresh. Here’s what dating expert Chiara Atik, author of Modern Dating: A Field Guide, told StyleCaster:

One of the ways to instantly make yourself more attractive and more presentable to other people is your clothing. It’s not so much what label or what trend, but that they fit well, and what state your clothes are in. People look more confident and more put together in clothes that fit them.That seems self-explanatory and obvious, but there are some people who just don’t put any thought into what they wear on first dates.

2. Stressing Out Too Much

Laurie Davis, the founder and CEO of eFlirt Experttells The Fashion Spot that you shouldn’t stress out too much about a first date outfit—it’s what you wear on the next few dates that are more important. How you dress after a first date can tell someone how you feel about them more accurately. For example, if you notice that you start dressing down, that probably means that you’re becoming more comfortable with the person.

3. Overly Ambitious Style Choices

I’m not suggesting that you forgo your favorite statement piece, but, when in doubt, less is more. In an interview with LuckyLauren Conrad spoke about her go-to date night outfit:

I try to go pretty neutral, especially if it’s a first date. I’ll wear a black skirt or leather leggings and a white silk blouse. I skew a little nicer just to be safe, but I think black and white is always sexy, and I’ll do a fun lipstick to dress it up.

Leather leggings are pretty pricey, but this faux-leather pair is just as sleek and stylish. As Conrad suggests, they’d look great under a basic blouse.

Sparkle & Fade Leather-Looking Leggings In Black, $52, urbanoutfitters.com

See similar: Leggings Queen Leather Zip Leggings, $25, Amazon

4. Bearing It All

Major snaps for having the body confidence to show off some skin, but on a first date, this can be off-putting. Instead, pick your favorite asset to show off. Maybe you have killer arms? Then wear a strapless maxi dress. Here’s what sexologist Nikki Goldstein told Yahoo:

When it comes to being sexy and flashing some flesh, it’s important to show one body part: legs, cleavage, shoulder, or back. Anything more and you run the risk of being viewed as trashy or too sexy. What message do you want to portray to your date, seductive sexy or bringing in all the men?

This maxi dress is a perfect example of comfy chic and shows just a hint of skin. If you’re feeling up for it, wear this with some bright heels. They’ll peek out as you walk. Want to show off your legs instead? Try an above-the-knee skirt with a long-sleeved top.

ASOS Bandeau Maxi Dress in Stripe, $38, asos.com

See similar: Annie Coco Maxi Dress, $23, Amazon

5. Dressing For The Wrong Type of Date

A handful of guys told Cosmopolitan their first date tips. One man explained why wearing your fave LBD may not be the best choice after all:

You may think, First date! I need to look amazing! But if you wear a LBD to a laid-back pub or a movie, you’re going to look out of place, which will make you uncomfortable…which will make him uncomfortable. Instead, dress for whatever it is you’re doing. Guys have a word for women who can be easy-going and fit in anywhere, and still look good doing it: Girlfriends.

6. Looking Unapproachable

If you look uncomfortable, then chances are that your date is going to feel uncomfortable around you, so wear something that puts you at ease. This is what celebrity style expert Bobbie Thomas said in an interview with Marlo Thomas:

You want to welcome someone in. You don’t want to be in something…constrictive. You look high maintenance and you can’t really be approachable. I personally love a cardi wrap or a cowl neck sweater. There’s something really elegant and kind of sexy about it.”

This cowl neck sweater is super soft and feminine. If you’re looking to show a hint of skin, you can pull it a little off the shoulders.

Free People ‘Pebble’ Cowl Neck Sweater, $118, nordstrom.com

See similar: PattyBoutik Cowl Neck Sweater, $37, Amazon

7. Having Your Hair Slicked Back

I love a sock bun just as much as the next gal, but this look might come across as too high maintenance on a first date. Let your beautiful hair be free! “Keep your locks long and free,” The Millionaire Matchmaker’s Patti Stanger tells Shape. “Men like to imagine running their fingers through it.”

8. Applying Too Much Makeup

You don’t want what you’re wearing to detract from what you’re saying. An example of this would be wearing so much lipstick that it comes off all over your teeth. Or if your body glitters starts to decorate the dinner table. Here’s what personal stylist Jules Sebastian told Yahoo:

Find the balance. Don’t over do it, but don’t under-do it either. You want to look like you have put in a good effort for your date from top to toe. Remember, (hopefully) he’ll spend most of his time looking at your face on your date, so don’t let it be distracting in a bad way.

9. Adjusting Yourself During The Date

No matter how many hours you spent getting ready, you always run the risk of a wardrobe malfunction. We’ve all been there. But instead of pulling a boob scoop at the table, excuse yourself to readjust in the restroom. Relationship mentor Yvonne Allen doled out this advice to Yahoo:

Rather than panic, remember we are all human. If near a rest room, excuse yourself and do what you can to fix the problem. If it is something that is apparent or likely to cause you embarrassment, usually honesty can be the best policy.

10. Wearing Something That Makes You Feel Like You Have To Suck It In

Why put yourself through the misery of wearing an outfit that you know is too tight when you could be wearing something that you feel good in? Not only will you look better, but you’ll also feel more at ease. Here’s another tip that Yvonne Allen gave to Yahoo: “Wearing an outfit that is too tight or uncomfortable never makes good sense.” First dates can be uncomfortable enough!

This dress is simple, sweet, and a great option for a first date. Its cinched waist will give you some shape while the flowey skirt will give you some room to breath.

Ray of Delight Dress, $60, modcloth.com

See similar: The “Charm Your Prince” Dress, $38, Amazon

11. Forgetting That There’s A Possibility of Running Into Someone That Your Date Knows

It’s not likely that you’ll be spending time with your date’s friends on the first date, but be conscious of the fact that we live in a pretty small world. There’s no predicting who you might run into. Here’s a little first date anecdote on Huffington Post from Michael Kors, who first told this story to author Sarah Z. Wexler for her book Awful First Dates.

In my twenties, I went to meet my date at a really chic, fashionable restaurant. I wasn’t dressed up necessarily, but I had one a nice shirt and jeans. My date showed up in cutoffs and a tank top. I knew half the people in the restaurant, who were all looking at me like ‘Who is this guy with Michael Kors?’ It was so embarrassing.

I hope that these tips make dressing for that first date even a tad less stressful. Remember that, in the end, it’s all about wearing what makes you feel good about yourself. With the right attitude, you can pull off anything. The cliche is true: the most important thing is to just be yourself. Good luck!

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