Visiting my former boyfriend – style advice needed

I am a young-at-heart 50 (aren’t we all, gals???) who connected with a former “after college boyfriend” through Facebook. I need some very inexpensive style recommendations. I am planning a visit to see him after 25 years. He’s really cute and hip (he’s also 50) and we have some unfinished business to attend to, if you know what I am saying….Jeans, boots, tops, skirts. I want to look hip but not tacky trying to look young when I am really 50…..Help!! p.s. I live in the east end of Louisville, KY. Thanks!!

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  1. Generic Image prplbfly says
    • First off Mary let me say WHAT fun!!! I too did this very thing, I am now 50, was almost 40 when I managed to meet up online with my HS sweetheart. Oh and yes we too had unfinished business. I don’t know how much of my story to tell, don’t want to bore you because you asked for tips not stories..lol but FYI we have now been married almost 11 years, my kids love him, he IS Grandpa to my 10 month old granddaughter, we were apart almost 20 years, and I had almost doubled in size. I was so scared to see him and fretted over what to wear, I had just lost about 40 lbs so at least felt better about me but still knew I was not thin and in HS I was like 5’9″ and 115lbs. So you can imagine my fear. Well here was my decision in the end, I had to wear something that I felt good in! I knew I was older and couldn’t look 19 again (that was last time I had seen him) We had both married and had families with other people, but had both just gone through ugly divorces when we re-connected! Ok I stray again, I ended up, first off it was cool when we re-met, I am a boot freak so I wore my favs with a nice pair of jeans, and I wore a very nice shirt/blouse that I love and also it had a good feel to the touch, just a little ummm help when his arm slipped around me for our greeting hug.  I felt 16 again and it took a long time to come down off that cloud, and to this day when he calls me on the phone from work my heart skips a beat. Sometimes, you can go HOME!!! Oh and as for makeup, don’t over do, remember he is 50 too, and many guys are truly turned off by too much, they do like a more natural look, but as we get older we do have to give a little help. So ok to sum it all up my suggetion is to BE YOU and be comfortable, but look fresh and think of the tectures of you clothing and maybe if you remember his favorite color or scent you can wear them. ;0) Always Always important to appeal to the senses. I hope this helps, and remember HAVE fun, I would LOVE to know how it goes! Do you have any past pictures? Those are fun to share too. My now in-laws still had pictures of us, that was too cool, because for my 40th birthday they had one framed and gave it too me. Ok enough of me…take care and Good luck, you will do fine!!! Rhonda

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    • Generic Image Rita@Goldivas says

      What a nice story, p. I like your comments on textures! Of course, choosing the most flattering color is good, too. Jeans with boots always look nice, anything that’s somewhat fitted, but not too tight or revealing. Skirts are nice too, especially if you have good legs.

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      • Generic Image MajorInsight says

        Be who you are.  Don’t  overdress for the activity.  Wear you favorite color around your face, make your eyes pop.  Simple blouse, nice fitting slack, jeans or skirt.  Nothing scratchy anywhere.  A cleverly tied scarf at the throat under a trench or parka, if it is still cold on your date.  This is a warm and cheap substitute for jewelry.  Wear your hair in your usual style, clean and shiny, with simple earrings.  If you are not certain about the activity or location, I would under dress, rather than over doing it.  Remember, you are a mature woman and you know who you are and you love yourself just as you are.  Own it.

        Finally, texture of the blouse or dress should be comfy to you, soft to him.  Your fragrance matters. Pick one that you have recieved compliments on from other people in the past.  Don’t forget you are never fully dressed without a smile. 

        Now you kids have fun.  I’ll leave a light on for you.

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      • Generic Image Mary Miller says

        I agree, Ronda had a great story. Thanks for the advice. we’re looking at end of May in Asheville, so skirt it shall be (my legs are probably a B) Mary

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    • Generic Image Mary Miller says

      I am remiss in responding to your very nice and fun response. Thank you for the great advice. We have plans to meet in Asheville at the end of May!! Will let you know how it goes! Mary

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  2. 50somethinginfo.com 50somethinginfo.com says

    Run, don’t walk, to the bookstore to pick up Sherrie Mathieson’s Forever Cool: How to Achieve Ageless, Youthful, and Modern Personal Style.  And check out
    http://www.50somethinginfo.com/Directory/Lifestyle/Wardrobe/Women's-Clothes.aspx

    for articles, websites, videos, and guides to update your wardrobe to not only please him but other former boyfriends you might have out there!  Best of luck.

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