I got this question sent to me and given the fact that my mother, who is now 58, has been a widow since she was 45 years-old, I’ve had my experience with helping my mother figure out what to wear to go out on a date.  I thought I’d share my advice for the woman who asked me this question here as I would imagine my mom and this new-to-the-single-scene woman aren’t the only two trying to figure it out:

Q: I am 57 years old and recently divorced. I want to start dating but I haven’t dated since Nixon was in the White House. Aside from my general fears about getting out there again, I think about my wardrobe and I feel like my style needs to change now that I am single. It’s not that I am unhappy about the way I look, but I worry that it won’t work for dating. Not only do I not know where to find things like this, I don’t even know what a 55-year-old woman wears on a date. Help!

A: Well kudos to you for getting out there. There are so many women who divorce and instead of looking for love again take comfort in a pint of Ben and Jerry’s and the remote control. So first, cut yourself a break, relax and pat yourself on the back for taking this step.

Now on to your wardrobe. What does a 55-year-old women wear on a date?  The answer is whatever she darn well chooses to wear. Women age like a fine wine and a woman with some wisdom under her belt possess a certain assuredness that the average 20-something dateable gal just doesn’t have yet. To me, you’ll wear this confidence better than any fabulous outfit that you can find at the store. Therefore, my first bit of advice would be not to forget this truth and embrace it rather than feel like you are at some sort of a disadvantage.

If you can identify that your wardrobe doesn’t contain much that would work for your new dating life, then look at your current style (that you said you like) and think of some pieces that can be infused into it that are more date appropriate. I am sure you own at least one pair of black pants. To start, get a few fun tops by a label or brand that you already like and wear with these black pants. It may not be a bad idea to purchase one simple, versatile dress that can be dressed up or down depending on the type of date you are going on.

As you are getting your feet wet, you may be going on a bunch of first dates, which means that you just need two or three “date outfits” in your wardrobe. Start slowly: It sounds like you are feeling like a fish out of water and the last thing you need is to feel even more self conscious by completely revamping your style. Just because you are dating does not mean that you have to completely stray from the style that you have known and loved or abandon what has been working for you. You want the guy to fall in love with you, not the shirt you are wearing. If you feel confident and good about how you look and feel, I can promise you, there will be a second date.



Bridgette Raes is the president of Bridgette Raes Style Group, author of the book Style Rx: Dressing the Body You Have to Create the Body You Want and a sought-after spokesperson, style expert and writer for many media outlets including CNN, Good Morning America and Real Simple Magazine. She and her Style Consultants are available worldwide for consultation, in-person or virtually.