The first date can be nerve-wracking on a number of levels. Whether you’re new to dating or an old pro, you want things to go well. And, you want to make a good impression.

I lied.  I’m not really going to tell you what to wear on your first date. You’re a mature woman with enough life experience to know how to dress. But, I do have a few suggestions.

I could tell you that men love feminine women so you should get all dolled up. Or that older men like younger women so make sure you look youthful. And, I could remind you that high heels are sexy, red lips too. But I’m not.

The Diva’s First Rule of Clothes and Dating
Be Yourself 

For heavens sakes, don’t change the way you look for anyone. The goal of the first date is to get to know each other. You want to be comfortable and at ease-which means wearing clothes you like, clothes that make you feel good about yourself.

That doesn’t mean you should wear your favorite baggy shorts. But you don’t need to squeeze yourself into body armour, buy a push-up bra and put on a floaty little dress and high heels. Unless that is what you normally wear when going out.

Tips for Choosing The First Date Outfit
  • Choose an outfit that makes you feel comfortable. If you don’t normally wear heels, then they’re a bad choice for a first date. Wobbling is decidedly unsexy.
  • Dress for the occasion. A casual coffee date, morning or late afternoon means you can show up in nice jeans and a top, or a slightly dressier pair of slacks. It’s not really the time to pull out your low-cut flowery dress or business suit, unless that’s your daily wear. Dinner at an upscale restaurant calls for something dressier (though it’s a bad choice for a first date, but that’s another post).
  • Be neat and clean. This is not the time to rush in from the gym–unless you’ve prepared your date for that.
  • It is true that first appearances are important. So, you do want to take a little care with your choice of an outfit. As with any occasion, you want to feel good about how you look.
  • Think about the message you’re sending with your clothes. If you show up for a first date in a very low-cut top or a sexy dress it’s a communication, of sorts. And, since you don’t know this person yet, you don’t know how he’ll interpret it. If you’re not interesting in jumping into the bed on the first date, I’d suggest you save that outfit for later.

There are no rules for how to dress on a first date, whether you’ve met him on an online dating site or in person. Some men, particularly older men (65+), prefer women in skirts. But if you don’t like to wear skirts then don’t. Do not pretend to be someone you’re not. If your date is pushing you to wear a particular outfit you should pay attention to that. Take note, then do whatever you want.

Be yourself. Like what you see in the mirror and you’ll be fine. The man who isn’t pleased with how you dress or look isn’t worth your time. He isn’t going to appreciate you. By all means use all the lipstick, hair dye and face cream you want. But be aware that you’re making superficial changes and understand why you’re doing it. Will you feel more self-confident without grey hair or wearing a face firming foundation?  Will it help you attract the right man?

What do I wear on a first date? Depends. On a recent afternoon coffee date I wore jeans and a very becoming black top with an interesting neckline. Hair down. Minimal makeup, no lipstick. I had a dinner date last week, temperature was about 95 degrees. The guy wore  jeans or shorts and t-shirts in all of his profile photos. So I wore a pair of casual slacks and a sleeveless top (and yes I have flabby ‘old lady’ arms). I’ve also done the skirt and feminine blouse routine (he was hot!). I match my outfit to the occasion and my sense of who I’m going out with.

Ultimately we all want to find the man who is drawn to our wisdom and beauty. A beauty that comes from being over the age of 50, of having matured into an interesting person with a history that informs our lives and our looks. Chemistry is a combination of ingredients; physical beauty is only one of the factors. When you feel good about yourself and can carry off your look with a sense of comfort in your own skin you will radiate your attractiveness. That’s really all you need.

What do you think about dressing for a first date? If you have questions about what to wear on a first date you can ask them here or contact me privately at


photo by Tim Walker, as seen on The Fashion Spot

2 Responses to What Are You Going To Wear On The First Date? Over 50 Dating

  1. says:

    Wonderful advice that will work for most any occasion. As you suggested, above all, be yourself. After 50, we don’t have all that much time or energy trying to pretend we’re someone we’re not!

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