Clothes for women over 50: What to wear on a first or second date

December 7, 2012 at 12:52 pm in Fashion & Beauty by VN Editors

What you wear on your first or second date will help dictate whether or not you get asked out on a next date. Your wardrobe will determine how you feel during the date and how you present yourself to your date, so plan it well.


The clothes you wear say a lot about who you are as a person. When you’re on a date, you want to present yourself well. If you’re going to pick the right thing to wear, you’ve got to learn how to avoid wearing the wrong things.

  • Don’t try new trends, advises eHarmony. Stick to your own clothes and accessories, and don’t splurge on some new fad. Remember that you want to present the real you during your first or second date.
  • Don’t be too provocative. Men love skin, but you shouldn’t flash too much of it during a first or second date. If you dress in a very sexy fashion, your date might get the wrong message about who you are and what you want. Stay away from skirts that are too high and blouses that are too low, but don’t dress too conservatively. Strike a happy medium, and avoid an outfit that looks too prudish or too provocative.
  • Don’t over-dress. You don’t have to be flashy to score another date. It’s better to stay understated and stick with a classy, elegant look, so leave most of your jewelry and high-fashion accessories at home.

Putting Pieces Together

Planning an outfit for a date is stressful. You walk into the closet, you see a bunch of different stuff, you get overwhelmed. Flattering 50 suggests that you focus on individual pieces you like, and put them together to create an outfit that makes you look and feel great.

  • Wrap dresses are great for first and second dates. They’re casual but not too casual, and they work well at a variety of events.
  • Blouses that are simple and stylish can be worn with skirts and slacks to create a variety of different looks. A drape neck T-shirt looks classy or casual, depending on what you pair it with. A silk or linen top can be worn anywhere, with anything.
  • Straight slacks are flattering and easy to dress up with jewelry and shoes. Choose a pair in a neutral tone, like grey, and you can wear them with any top in your closet.

When in doubt, always turn to a little black dress. It’s a dating go-to garment, and according to the New York Post it’s a secret weapon. The basic black dress can go anywhere and always looks good. A good black dress will make you look sexy, elegant and feminine all at once.
The Real Secret Weapons: Shaping Garments

Some of the most honest advice about putting together a dating wardrobe came from a VN member…who’s male. The Makeover Guy names two must-have garments for dating: “a good bra for when you’re approaching and a good shaper for when you’re walking away.” It’s more than just a funny answer. Shaping garments are a great way to get yourself that next date.

“I have more jiggles than I would like and…occasionally wear shapewear. But, I believe in presenting the real me to men I meet,” said VN member Walker Thornton. Everyone’s got a few extra jiggles, and shapewear is great for smoothing those bumps, flattening that fat and keeping everything in place.

But let’s face it: Shapewear isn’t sexy. Some women avoid it because they think it’s a misrepresentation. Others don’t wear it because they like sexy underwear instead.

“At age 64, I was holding this lacy, sexy demi bra and trying to decide if I should get it.  Thinking nobody other than me would ever see it.  I expressed that to the young woman clerk and she said, ‘but you’ll know you have it on.’  Sounds so simple, but it was staggering to me at the time.  You know I bought it and it started a trend for me.” VN member Pam shared her story of sexy underwear, and it’s a good one. Even if you aren’t dating, if sexy underwear makes you feel good that’s what you should wear.

“Feminine sexy undergarments make you feel beautiful and confident!” Wrote VN member SapphireSky. “The fact that men will respond to this is related more to the glow of self-esteem.”

Some shapewear can still be pretty sexy, and if it’s made well your date won’t know you’re wearing it. When it comes to undergarments, observe this rule: wear it for you, not for your date. If you feel good, you’ll be more likely to get to that crucial undergarment moment with a date. And at that point, he won’t care what you’ve got on under there.

The Messages Your Clothes Send

“Clothes support the message, but remember they also send a message that can enhance or detract from who you actually are, and what you’re actually saying,” VN member Sandy Dumont, of The Image Architect, reminds us. “Most of all, have fun, enjoy this new adventure, and remember that the way you dress announces the way you feel about yourself.  Others will see that and treat you accordingly!”

“Do you have something in your wardrobe that flatters you-that makes you feel good about yourself?  The cut, the color, the decoration?  Is there something that you put on whenever you want to look unique/special?” Asked VN member Melinda Giordano. Her advice, to wear what makes you feel good, should be followed. When you feel good about yourself and the way you look, you’ll actually look better to others.

And as always, don’t forget to be yourself. “Are you a neat and fun person?” Asked VN member JoJami. “Your clothes should reflect that!”

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