@heymrssolomon

@heymrssolomon

Share this post

@heymrssolomon
@heymrssolomon
Preppy, w/o the a-hole. And make it me, plz. 8 takeaways.

Preppy, w/o the a-hole. And make it me, plz. 8 takeaways.

No need to be a c*nt at the country club

Hey Mrs. Solomon on Style's avatar
Wendy Duffy's avatar
Hey Mrs. Solomon on Style
and
Wendy Duffy
Jul 14, 2025
∙ Paid
60

Share this post

@heymrssolomon
@heymrssolomon
Preppy, w/o the a-hole. And make it me, plz. 8 takeaways.
12
2
Share

Sperry was one of our very first clients when I founded

Honor Code
. We did so much, lots of it was concepting campaigns for holiday, back to school, etc. It was such a nostalgic brand to me, one I grew up on in New England. Sometimes a new CMO would come in and make a change. One in particular spent huge money on an NYC agency known for its risk taking. They came back with this line: “prep for all.” Sperry called us again because they didn’t know what to do with it.

I thought the concept was really smart. The democratization of prep. Decode the codes. Not IYKYK. Instead, let’s all know more together. Sure, one take is — everyone gets to be part of prep. But that’s one sided. How about — prep gets an infusion from everyone and what they bring with them, the richness of multiple experiences.

In my wildest dreams, I pictured something like this from

Jalil Johnson
‘s recent post referencing Michael Rider for Celine.

Prep is, as they say “having a moment” - especially this 80s iteration. (Especially nostalgic for me since I was in prep school in the eighties at Dana Hall.) But for me it’s a fraught with the us vs. them-ism I still feel in New England summers. It can also feel like a costume!

For a week in outfit planning, I thought it made sense to try playing with some of the tropes and pieces and seeing if they could feel inclusive, individual, unstuffy and accepting. Here is the outfit planning session. I had some good aha moments. Here they are, along with what I wore.

Be part of a self-selecting group of grownup paid subscribers who make long term connections, get real value, and become in some small way - friends. (If you want this and are facing real financial concerns ask me for a Standing Coffee. You belong here too.)

(OH, and also. I took myself on a field trip to Ralph Lauren. It’s the iconic prep brand, and I’m not saying it’s inexpensive, but outside of the Purple Label/collection it offers a lot for a lot less than some other brands do if you can make it your own. On my visit, I pulled all the pieces I thought were really great. Here I’ve collected them and explained why. )

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2025 @heymrssolomon
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share