Ladies: How to Dress on a Date

I just reconnected with a former co-worker and friend whom I hadn’t see in a while. She is a single mom who’s done an amazing job of raising her daughter, who’s now in another state in her senior year of college. For as long as I’ve known this woman I don’t believe she’s ever dated. She happened to mention it to me that she was trying and seeing where it goes.

Good for her! If she’d ask me, I’d be glad to give her some style advice for her dates. Now I admit, it’s been 22 and a half years since I have been on a date. When I think about what I, your Indiana Wardrobe Stylist, wore on those “said” dates, it is a wonder my beloved ever asked me out again.

Indiana Wardrobe Stylist Tips for Dressing Fab On a Date

  1.  Without being too nosy try to find out what you’re doing on the date, and then dress for the activity! For instance, if you’re going boating, don’t wear a frilly, sheer dress that might get caught on the oar! Shorts and an interesting shirt or even cotton cami would be great. Now is the time to show your cool sneakers. Don’t wear skimpy sandals or heels!
  2. Indiana Wardrobe Stylist advice for a first dateIf you’re just going out to dinner, whether it’s your first date or your 10th, now is the time to wear something a little more fun, and daring that shows your personality. As an Indiana Wardrobe Stylist, I always love wearing a dress on a date, from casual with wedges to something more pretty with heels. If you’re going on a really long walk after dinner though, nix the super high heels.
  3. Don’t forget to play with accessories. Earrings, necklaces, bracelets, and rings add so much interest. I also love to wear hats in the summer! It’s different.
  4. Don’t overdress. For instance, avoid wearing an occasion dress and shoes to a simple dinner. It means you’re trying too hard.
  5. If you get cold easily, bring a third piece such as a blazer, sweater, or even denim jacket.
  6. Don’t forget your purse, credit card, money, etc., and phone of course. In those rare instances when the dates really go south, you need an escape plan. Always have Uber loaded on your phone or the taxi number.
  7. Remember to be a good conversationalist. It’s important in dating to really listen to what the other person says. You need to get to know that person to see if it’s someone you want to see again. If you don’t feel any romantic connection at all, maybe you’re just made a new friend. When I was in college I really learned how to have male friends. It was good for me and it prepared me to be a good friend to others.
  8. Keep makeup and hairstyle simple but chic. There certainly isn’t anything wrong with wearing your favorite lipstick or eyeshadow on your date. You want to put your best self forward.
  9. Don’t forget one of your best assets is your smile. Be kind and polite.
  10. If you’re going to dinner. remember your table manners. If you need a brush-up on etiquette, please reach out. As an Indiana Wardrobe Stylist, I do etiquette training as well.

If you have more questions about what you should wear on a date, do not hesitate to reach out!

Keep it sassy, Indy.
Beth Divine, MA, AICI-CIC

Personal Image Consultant and Indiana Wardrobe Stylist