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.
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.
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.