Dressing For Graduation for Women Over 50

Dressing For Graduation for Women Over 50

I love the pomp and circumstance surrounding graduation ceremonies. It celebrates success and the end of studies. It also brings the excitement of new beginnings. It’s fun to see new graduates flip their tassels after they receive their diploma. My heart nearly burst with pride as I watched my own children receive theirs.

Welcome to this week’s Hit Your Style Sweet Spot, my weekly collaboration with Pamela Lutrell from Over 50 feeling 40!

Style Sweet Spot

Your Style Sweet Spot is when you know your appearance is sending the message you intend and feel confident you look your best. Last week Pam and I shared how we dress for a cruise…this week we’re dressing for a graduation.

Whether the graduation ceremonies are held inside or out, I always think it’s a nice occasion to dress up. I love the formality of a little black dress and hat. Our weather has turned a little chilly, so I’ve added a cashmere wrap.

Wearing a little black dress, pearls and a hat for graduation is classic.

This is my favorite cashmere wrap by Catherine Robinson Cashmere. It’s my favorite shade of soft, blush pink. This is one of those colors that looks good on most women. I’m careful to wear it with neutrals or strong colors so it doesn’t age me. Pastels are funny that way, they can make us look older than we are, if not paired properly.

I love the combo of blush pink and black

I love how it looks with black and pearls. Something about that combination feels very Chanel like to me.

I like to use a small compact handbag that can sit on my lap during the ceremony. If the ceremony is held outside, my hat protects me from the sun. If inside, it’s not too wide for others to see around.

A simple black dress, black accessories with a pop of pink and pearls feel perfect to me. This is my Style Sweet Spot for what to wear to a graduation.


Now lets pop over to see how Pam hits her Style Sweet Spot going to a graduation.

Have a fabulous week!

xo Jennifer

This post may contain affiliate links which won’t change your price but will share some commission.


  1. May 24, 2016 / 8:03 am

    I love those pearls. Particularly the grey. Stunning.

  2. May 23, 2016 / 4:26 pm

    You look amazing! I love that wrap and the colors wow.

  3. May 23, 2016 / 11:59 am

    I’m a big fan of hats and you carry it off so well! I love the outfit for the occasion. Very classy.

  4. Cindy
    May 23, 2016 / 10:30 am

    I absolutely love the pearls layered the way you have!

  5. May 23, 2016 / 8:53 am

    You’re channeling Audrey in Breakfast at Tiffany.

  6. May 23, 2016 / 8:12 am

    We just went to a graduation this weekend—and I took a sweater (for the inside—the A/C was freezing!!).
    I tend to steer away from black right now (it’s a stage I’m going through), so I went with pink & white—maybe too young?
    I love your hat—I can’t believe I forgot to wear a hat to the one we attended—-I wish I’d seen this sooner!

  7. May 23, 2016 / 7:08 am

    I love your look! The wrap is perfect. My problem with a hat is then I have hat hair so I can not take off the hat. For a quick event wearing a hat is fine but for a longer event like a wedding dinner reception, the hat must come off!

  8. Susan
    May 23, 2016 / 6:44 am

    The hat revolution has begun! I have always loved hats but rarely wore one except at the beach. I have been inspired by your cute hats and last week I not only cut 6 inches from my hair but I also bought several cute hats. I spent Sunday afternoon running several errands and felt polished and feminine wearing a cute straw hat. Thanks for the inspiration!

  9. May 22, 2016 / 2:38 pm

    You look stunning Jennifer thank you for modelling my wrap so beautifully.
    I hope you had a wonderful day.
    With love xx

    • Jennifer
      May 22, 2016 / 4:24 pm

      Thank you Catherine! You make the very finest cashmere. I love it!

  10. Yitka
    May 22, 2016 / 12:41 pm

    I’m the 50 something graduate. I’ve finished my doctorate and will be graduating in July. The weather here in the UK can be unpredictable . The graduation gown is navy, not black and the hood is jade and nasturtium, which is a bright orange. The latter really limits colour options. I’m thinking a navy shift dress, patient alligator pumps (not too high) and pearl earrings. The ceremony is first thing in the morning, so a hair appointment not possible….any advice?

    • Jennifer
      May 22, 2016 / 4:23 pm

      First, huge congratulations!! That’s a fabulous accomplishment! You should be very proud.
      The navy sounds perfect. I find hats…so caps, usually look most flattering on me with a little hair around the sides. Not too much or its over powering. Is your hair long or short?

  11. Canuck on
    May 22, 2016 / 11:21 am

    I attended my son’s graduation this weekend. I had great plans for what to wear, starting with a sleeveless cornflower blue and white swing dress and matching blue peep toe wedges. Got a pedi and mani for this. Hmmm, it was a little cold when we headed out the door at 7 a.m., so I added a matching blue faux leather jacket and light scarf. Right! Still looks put-together. This was an 8 a.m. start (!!!) for the indoor event. Still freezing, so I left the jacket on the entire time. Others were wearing overcoats for the duration. At least my ice-cold blue skin matched the outfit.

    Now move forward to the family banquet and dance in the evening. I’ve changed into a below-the-knee ivory, white and black swing dress with a black lace and voile three-quarter sleeve jacket, black evening bag and soft gold shoes. We’re walking in a huge convention hall, where three school graduation banquets are taking place simultaneously. Moving slowly through the crowds, the concrete floors now slightly slippery, as the cold has turned into rain, the strap on my brand new slingbacks breaks. No, I don’t fall, but shuffle the rest of the way to our destination. Fortunately, I have brought along a pair of black flats. Slingbacks out, flats in.

    Time for the mother-son dance. More shuffling through the crowds to the dance floor, finally getting to the mosh pit, so crowded to overflowing that we arrive to dance for all of 30 seconds — on carpet.

    Now it’s time to go home, but the rain has turned to snow, so I’m wearing husband’s overcoat. I didn’t plan for snow, and they said there would be no coat check for this event.

    Well, at least my hair and makeup held out for the 16-hour day!

    Maybe I over thought this wardrobe issue. Maybe I under thought. Maybe I should have brought a parka, boots and mitts. Definitely I needed the touchup makeup in my evening bag to hide the bags under my eyes from this very long day. So even though the strap broke on that, too, it was worth it to bring the makeup.

    The thing is, this event wasn’t about me, and what I wore. It was about those young people. All eyes were on them, and they looked amazing!

    So go to the graduation, be comfortable, bring a wrap or jacket for air conditioning or unexpected bouts of winter in May. Wear shoes that are made for standing and walking (but still look nice). Remember it can be slippery. And bring the touch-up makeup for a very long day.

    Have fun!

    • Jennifer
      May 22, 2016 / 4:19 pm

      What an amazing day!! Thank you so much for sharing with us. The best laid plans and all that… You sounded prepared for everything. And everything happened. I admire your planning and organization. You’re so right. It is all about them! Your outfits sound beautiful.

  12. May 22, 2016 / 10:20 am

    You look lovely! I’m attending my daughter’s graduation in a couple weeks – held on the Midway in San Diego harbor. So excited! So proud of her. Can’t wait.

  13. May 22, 2016 / 9:31 am

    What a beautiful color that wrap! Looks very good on you!

    • Jennifer
      May 22, 2016 / 4:11 pm

      Thanks Nancy!! I adore it.

  14. jenniferanne
    May 22, 2016 / 9:06 am

    As an ex- pat Brit I can say it is true that many Brits do wear hats for special events. They can actually rent them. As for Brits having a classy style I would have to respectfully disagree – hats yes but usually too much bare flesh for my liking.

    I do like this outfit, though Imust say I would prefer a slightly longer dress at least for me;)

    • Jennifer
      May 22, 2016 / 4:11 pm

      I’m not overly familiar with how much skin Brits do or do not show. I think it’s a universal issue. I’d probably like this dress and inch longer too. Alas, I’ve owned it many years and still enjoy it.

  15. Mandy
    May 22, 2016 / 5:07 am

    I am a little confused ( happens easily at my age). If you don’t wear it with neutrals, and you don’t wear it with strong colors, do you only wear this shade of pink with black or white?

    • Jennifer
      May 22, 2016 / 6:12 am

      I meant I always wear blush pink with neutrals and strong colors, so it doesn’t age me. I’ll go back and check my wording! Thanks!

  16. Karen
    May 22, 2016 / 4:47 am

    You’re right, a very classic and Chanel look! I am a fan of hats, and yours is beautiful. You look rather British here, and British ladies seem to have classy style locked down! Love this look for so many occasions! Good tip about pastels.

    • Jennifer
      May 22, 2016 / 6:14 am

      Thanks Karen. I love this classic look too. It can go many places and be perfectly appropriate.

  17. May 22, 2016 / 4:14 am

    There were two women at the graduation dinner I attended yesterday who wore hats. I am about to go shopping…I really want a hat! You look perfect for graduation.

    • Jennifer
      May 22, 2016 / 6:15 am

      You can start the “I wear hats” revolution in your town!

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