Dressing for Your High School Reunion

Hi Deborah, 

I follow your blog all the time even though I’m well over 40, actually 67 but I like to be thought of as somewhat fabulous. I’d love some help with my upcoming 50th High School Reunion. Dress is “business casual”?

I sew and I made a jacket (reunion pic #5) for the occasion but I think it’s a little too much. So, I’ve been going through my closet to find something more comfortable and appropriate.

A fan, Leslie.

 

high school reuinion 1

Outfit # 1

Outfit # 2

Outfit #2

outfit # 5

Outfit #5

high school reunion 3

Outfit # 3

high school reunion 4

Outfit # 4

Deborah BolandHi Leslie,

You are certainly fabulous and I’m happy to share your photos! I like your outfit #4 with the long grey sweater because it shows off your adorable figure and is the most youthful looking, but I also think you look stunning in the gold jacket and it would make you stand out in a crowd.

If you did go with the gold jacket, I think it needs a different shoe. The rounded toe seems a little too casual so maybe one with a little heel and more of a pointy toe. The long grey sweater looks chic, but the gold jacket is pure Glam! Either would look great.

As for the long black skirt in outfit #1, I suggest you retire that, as it is matronly compared to these other cute outfits. The white jacket in #5 – yes I agree, it’s too much. Also the jacket seems to make your arms look rather short and makes you look heavy up top, at least in this photo.

I also love the smart olive green jacket with the cuffs in outfit #3, but I wouldn’t wear it for the reunion – not enough color.

Leslie, you are beautiful and a real inspiration. Have fun and I hope I’ve helped.

What does everyone think Leslie should wear?


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  1. I vote for outfit number 4. Amazing! Is there any way to subscribe to this blog via email subscription?

  2. Dear Leslie,
    Go for the gold! (Jacket, that is!) I second the suggestion of you wearing a dressier shoe with a kitten heel perhaps; also, you could add a long necklace with a pendant in a gold or bronze tone, or a long, softly patterned silk scarf that picks up the gold color. Peachy gloss on your lips, and you’re the belle of the ball! Have a great time, Leslie!

  3. Mary Huggins says:

    She should defifnitely wear photo #2 gold jacket. I would wear slimmer black slacks, the shoes in phote #3.

  4. #3 gets my vote…& I’m the same age, going to my 50th hs reunion next week in NJ & still don’t know what to wear, except for black slacks & heels.