Dating After 50: What to Wear?

Any day now, the warm sunshine will begin to coax people out of their winter hiding. What is it about warm temperatures, new grass, and flowers popping out that is so reinvigorating? I remember as a teenager getting the love bug every spring, feverish for a new romance. A good friend of mine, hardly a teeny-bop at age 51, is definitely feverish for a new romance these days. Her husband left her 2½ years ago and she’s ready to start dating. Last weekend, I helped her fill out her profile on one of those online dating sites. Already, she’s got men who are interested in meeting her. That’s got to feel good. Soon (I hope) she will be ready to start arranging “first dates” with a few of the men. She’s got decisions to make, including what to wear.

For this post, I've gathered a few tips on choosing a "first date" outfit as well as some fashions available online. Sorry about all the young babes. But there aren't many dress makers using older women as models...yet.

FIRST DATE STYLE DO's AND DON'Ts

Do plan your first date after sunset—that’s the best lighting for our mature complexions. A bar or café with candlelight is an excellent choice. It’s like a fog filter! Let the guy get to know you a little bit, soak in your many attributes, before you show yourself in the light of day.

Do choose a ‘first date’ outfit as soon as you complete your online dating profile. That way, when you start dating, you won’t drive yourself mad trying to decide what to wear. Where you go for the second date may vary, but the first date should always be an “easy in, easy out” location like a coffee shop, bar or café—someplace you can meet for an hour (or less) to see if there’s any chemistry.

Do wear an outfit that makes you look like a million bucks. Most men love it when women dress up a little for them. That may mean a nice top and slacks or a simple dress. Just make sure it’s something you feel comfortable in. Only you know what makes you feel gorgeous and confident. A wrap dress flatters just about every body shape. This Jones New York Rose Faux Wrap Dress, ($134), with its full skirt, is lovely and comfortable.









Or, perhaps, you feel most comfortable with a feminine top and a pair of slacks. I love this Michael Stars Slub 1x1 3/4 Sleeve Drape Neck Tee









If you like a collar, but don't want to look corporate, a denim suit is a casual alternative.




Chambray-Shirt



Or the colorful cardigan with camisole is always reliable. Too blah? Try adding a pretty necklace.



Cashmere-Round-Neck-Cardigan ($118.40) in 8 colors.



Do dress honestly. If you’re not looking to jump into bed right away, don’t wear something with a plunging neckline or that’s skintight on the first date. By the same token, if you aren’t a sweet and demure Donna Reed type, don’t wear a high-neck, calico dress with pearls. Try to give a true first impression.

Don’t wear something new for the first date. If you don't feel you have anything in your wardrobe, you might have to buy something new. But buy it and wear it a few times before the date to make sure it's comfortable and makes you feel gorgeous. Also, you don't want the outfit to only be associated with the first date. If the date goes poorly, the dress will have an unpleasant association.

Do go home and change, if your date is after work. You want to convey that you’re someone who loves life, who is fun to be around. Work clothes usually don’t convey that. A pretty dress will.


Don't think that first impressions won't count. There's no getting around: people form opinions based on how you look. Hopefully, your date will quickly put those first impressions aside as he learns about who you really are. But because of the oh so human behavior of judging based on appearance, you should think about what impression your outfit will give. For example, I don't think you should wear all black, show cleavage (that's always a no-no for over 50), or wear a big, loud print. All those things could potentially send a message other than the one you want to send.

You also don't want to wear something that draws attention to your little imperfection. You've got enough to think about on a first date. Personally, if I were planning to wear a sleeveless spring dress for a first date, I would wear a 3/4 sleeve shrug or sweater to cover up my over 50 arms. Or, perhaps, this Jones New York Long Sleeve Drape Front Cardigan (was $109, now $81.75) with soft ruffles.





Good luck!