High School Reunion: What I Wore

High School Reunion: What I Wore

The invitation was sent by email, the agenda was crystal clear yet I had no idea what to wear.

It was my husband’s 50th prep school reunion in Connecticut. He hadn’t seen these guys since graduation, I’d never met them. He hadn’t seen his school in 50 years, I’d never been there. On a good day, Mt. AWSL isn’t good with dress codes and in this case, he had no idea and there was no one else to ask.

We flew in a few days early to explore the Rhode Island and Connecticut coast. The weather was gray and cool with the promise of rain so I was glad I’d packed layers.

We met up with his classmates and their wives for a get reacquainted banquet dinner prior the night before the school event. The wives were dressed in sneakers, sandals, loafers,  jeans, chinos, crop pants, blouse, sweatshirt, tee, and blazer. They covered the gamut and there wasn’t an opportunity to ask what they planned to wear the following day, so I winged it.

The agenda was as follows:

  • Meet chancellor for a welcome back meeting in the new administration building.
  • Tour of the school.
  • Lunch by the lake and volleyball on the beach.
  • Alumni basketball game.
  • Cocktails and dinner.
  • Ceremony in the chapel to induct the class of 1969 basketball team into the school’s hall of fame.

I assumed the induction ceremony in the chapel would call for a skirt so I packed one along with hose and a slip. Viewing the basketball game called for sneakers and pants to sit on bleachers so they got packed too. Volleyball called for nothing because I had no intention of playing :). Dinner called for something nice that wasn’t too dressy.

In the end, I put my own spin on classic items. I wore black jeans, a plain black tank with a Chanel-type tweed jacket and the black ballet flats. I  kept my jewelry very simple and used a cross body bag to keep a hand free for greeting people.

Jennifer Connolly of A Well Styled Life wearing silver hoop earings and tweed Chanel-type jacket

jacket similar // top // earrings similar // crossbodybudget option

The jacket helped me look dressier when seated for dinner and in the chapel. The jeans and flats were perfect for climbing up and down the wooden bleachers and the simple jewelry kept everything casual.

Tweed Jackets

Wearing a jacket adds polish to simple jeans and a tweed one bumps that a notch. It would have been easy to look way overdressed at this casual event, and the invite gave no indication. I prefer to be overdressed than underdressed but I don’t want to stick out like a sore thumb.

In the end, I wore what made me feel confident.

What do you reach for when you have no idea what the dress code is and are unfamiliar with the situation?

Thanks for reading and have a great day.

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Affiliate links within this post may generate income for AWSL at no additional cost to you. When you shop through my links, I earn a small commission which helps support my business.


  1. May 7, 2019 / 3:55 am

    First of all I live in that area and we have had a month or more of hit and miss showers and grey skies. That’s April in New England. I feel for you, really I do.
    I wouldn’t have a clue as to what to pack….if I lived in sunny California and had to travel here. It looks like you scored a home run, Jennifer. Your outfits look warm enough, yet stylish and becoming. Hope you had some fun!

    • May 7, 2019 / 7:21 am

      Thanks, Paulette. It was fun to hear stories from when my husband was a teenager 🙂

  2. Penelope
    May 7, 2019 / 4:27 am

    I had to chuckle at the previous response by Paulette who used the term “ sunny California”. I was born and raised there and the weather is different all over the state. Many places are rarely sunny! Lots of unpredictable wind, rain and fog. We had a difficult time dressing for the unexpected.

    Black somehow seems to be key to dressing an outfit up or down. Since I don’t wear black I find myself frustrated with my wardrobe flexibility. Trying to find other neutrals that match is crazy making!
    Your outfit is great and you look chicly casual. I’m sure your husband was proud of you. I say “ good job”

    • May 7, 2019 / 7:22 am

      Thank you, Penelope. It is more difficult when you don’t wear black. I’m sure you know deep brown and navy are great substitutes but not as readily available.

  3. Talitha
    May 7, 2019 / 4:27 am

    Very chic, Jennifer, and not over dressed. I’m sure your husband was proud to have you on his arm! Sounds like everyone was confused about the dress code.

    • May 9, 2019 / 5:08 am

      Thanks, Talitha. I think they were confused because the wardrobes were so diverse.

  4. Linda
    May 7, 2019 / 5:30 am

    I think you made smart choices!

  5. Sue L. Petersen
    May 7, 2019 / 6:31 am

    Well, I have two 50th reunions this year. Mine is Memorial Day weekend and my husband’s is the end of July.
    I think your outfits were great! I have two outfits planned for mine as I want to be able to choose. One is a mint green jacket with navy flowered shirt (mint colored flowers) and navy slacks. The other is a navy color blocked sweater with navy tank top and navy slacks. Our class has a reunion every 5 years. No one wore dresses the last time. My husband’s reunion is at our house. We are having a barbeque. It will be more relaxed and of course hotter weather in July. Will have to figure out yet what to wear as I will be busy doing hostess work and not just sitting around. I loved your post today as it was very helpful to me! I think you did a great job of what you wore! It is hard to dress for a whole weekend of activities. I do love the jacket that you wore!

    • May 9, 2019 / 5:11 am

      Those looks sound great and the pieces are interchangeable which gives you options to switch things up if you need to.

  6. Rose Brock
    May 7, 2019 / 6:39 am

    I think you looked perfect. In those situations I always reach for black and classic also. It always looks chic.

    • May 9, 2019 / 5:13 am

      I’d have a hard time without black in my wardrobe. It’s perennially stylish and dresses up so well.

  7. May 7, 2019 / 6:47 am

    Those events are always tricky aren’t they? I grew up in a small town in the midwest and everyone dresses every way imaginable for the reunions!

  8. Glenda Norville
    May 7, 2019 / 6:53 am

    Well done. Classic. Can’t go wrong with that!:)

  9. May 7, 2019 / 7:09 am

    Your look is just right and very approachable. I had my 50th last October in Maryland. It included a meet and greet the day before and dinner the next night. The dress was “business casual”. I wore black jeans and nice top. The next evening I wore a black and ivory skirt with ivory top and dressy black topper. Had to purchase black shoes to complete outfit. I felt just right and comfortable. In the end I saw lots of variations from LBD to nice pants and top combos.

    • May 9, 2019 / 5:15 am

      Can’t go wrong with black and cream, It’s such a classic, elegant combo.

  10. Joanna
    May 7, 2019 / 7:56 am

    I love a dress code. How to dress for the occasion is then very obvious. As a wife of a military man, we always had dress code so it is not new to me.
    I love your Chanel type jacket. It really does elevate your casual look. It was a tricky day to dress for with all the different activities. You nailed it!

    • May 9, 2019 / 5:05 am

      Thanks. I love dress codes too and can usually figure them out based on venue and occasion. This one had me puzzled.

  11. Jill
    May 7, 2019 / 10:56 am

    You are a professional when it comes to clothes and style. When you see a woman who looks well dressed can you tell if she is wearing very expensive clothes or more budget friendly?

    • May 9, 2019 / 5:03 am

      If a woman chooses wisely and is put together stylishly, the cost of her clothes isn’t evident. Crooked seams, loose threads, and poor craftsmanship would be the giveaway. Budget-friendly garments are available that do not look shoddy.

  12. Gail Schwartz
    May 7, 2019 / 11:48 am

    Hi Jennifer! I’m going to my 50th college reunion at the end of May, in the Boston area. Thank you for reminding me that I bought a navy, Chanel-type jacket at Talbot’s last year. It’s going to make a good outfit for one of the events. It’s tricky when you have to travel with outfits for several events. I’ll be doing a “what would Jennifer wear” when I do my packing

    • May 9, 2019 / 4:56 am

      Have fun Gail! Those Chanel-type tweed jackets are great for all types of looks.

  13. Kathy
    May 7, 2019 / 12:37 pm

    I love the blue jacket! It looks like a much brighter blue than it shows in the link. Did you wear your usual size or were you able to go down a size?

    • May 9, 2019 / 4:50 am

      I’m wearing the medium, which is my regular size in this brand. I usually wear an 8-10 in jackets.

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