Preppy, w/o the a-hole. And make it me, plz. 8 takeaways.
No need to be a c*nt at the country club
Sperry was one of our very first clients when I founded
. 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
‘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.
(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. )
First, the takeaways.
I actually love traditional “prep” pieces and bet many of you do too; it’s often about context/styling. They fall into what I call “king” or “dad” and Tibi calls “classic” styles. To make them feel modern and not literal, it’s about either (or both) (1) choosing updated prep pieces (2) styling classic prep pieces like Ralph ones differently.
My Security Blanket formula works — one part prep, one part security blanket item, one part something firmly right now. (often Tibi enters the calculus as the security blanket or the right now)
With a polo shirt, go for oversized or shrunken vs in between. Try buttoned all the way up or not at all. And roll the sleeves.
With a buttonup, same as above, but also try one or two buttons.
Surprisingly, one way to de-classic your prep is to add more of it. More stripes, more prep codes, etc. That injects fun and humor.
Another way to de-classic it is with a shot of “poison.” Add a wrong color. A bad color. Something not in good taste. To make it fun, self aware.
Use the humor, boldness, and ease to generate approachability. What I find offensive in prep is any attempt to look wealthy or be stealth and all IYKYK. Adding humor, making people smile, inviting everyone in on the fun takes that offense away.
And - need a baseball game uniform? I went to two baseball games in the course of a week. And I think a solid neutral tee; dark eased out shorts; pulled up sock in a classic color (red, blue, green, taxi yellow); small crossbody + loafers is a way to say “ballgame” without needing to be so literal in a jersey, sneakers etc. And interesting good cap is useful too.
MONDAY
What:
Thrifted Lacoste polo … here are some favorites. (don’t forget the men’s department)
old Dries shorts + more options for you
Tibi past season brown square loafers and others
Gucci tote … lots of good options here
Why:
Having a normal workday; lots of writing, etc. Followed by Red Sox game w/hub. I felt this did the job — tidy and comfortable. game-y, esp with the sock. The brown loafer and bag calm the stark-ness of the white/black blue. I added a red bandana on my wrist at game time.
Outcome: Lofted Settledness.
TUESDAY
walk/work/workout
What:
Melissa Shoes x Jason Wu rubber fisherman sandals but will I cave and order these by end of summer? If I’m being honest, probably - they BEND and can be worn all year with a sock.
secondhand Fendi camo crossbody mom gave me - such good options!
plaid Barneys shirt stolen from hub (this is $12 it could be anything)
Why:
Getting into the rhythms a LITTLE — made time for pre-workout coffee run. This is just to say - why is all our workout wear solid now? Print mixing with it made me feel a little more something.
Outcome: Loved. Would be great with a little leather shoe. Something more incongruous.
Later
Tibi pull on skirt and more good summer white options
Jamie Haller 2 buckle croc emossed sandals and more selections here … or maybe you dare to dream? Ultimate. Also these which I tried IRL; they were very comfy.
La Ligne Margo tee with fitted tee faves
Lemaire single breasted nylon-y blazer (secondhand) and other options we like
one of a kind hand made buckle necklace from Gushi Studio
Why:
Full day, writing, etc. In town. The blue tee with the white skirt and sandal was very prep, very Vineyard-y. Adding the special necklace helped make it less nautical and … less Karen-ish (?) It also echoed the buckle sandal. The icky color blazer helped too. And I put it on while in AC.
Outcome: Lofted Settledness.
WEDNESDAY
What:
orange/red shoes Camper (about 3 years old) and other options to do the trick
Falke cotton socks - look at these colors!
Why:
A best friend in town for the day. Celebrated her b-day walking (about 14k steps), talking, shopping, eating. I wanted a bag to put things in and comfy everything with a little oomph. Here the poison of acidic red cuts the prep of that mint Lacoste.
Outcome: Lofted Settledness
Later
Swapped out the tee added my check shirt and Margiela x Loubs, dropped the bag off and went with Leslie to my favorite wine bar rn.
Why:
The place was casual, but I wanted to feel just a little of “I’m out.” The texture of this shirt is really good and adds a lot. The black white pallette feels going out-y. So does the sparkly shoe. And the shoe is weird, which makes “buttonup and khakis” feel not prep versus say a loafer.
What:
Outcome: Lofted Settledness.
THURSDAY
What:
Pearls tee (it’s an Australian skater brand) - here with other simple graphic tees; we keep updating these!
Secondhand Lauren RL seersucker pants (mine + a few options)
Tibi Charlie shirt, sold out, here are more striped options
Secondhand Stewart Weitzman jelly thongs
Why:
Meeting Alyson Jenkins (who wrote last week’s Gems with me) for a walk in a shopping mall on a rainy day. I also walked there (about 40 mins). These shoes are actually great for walking, and ofc waterproof. I wanted to be in a tee for all that walking. With the seersucker I thought adding another stripe made it fun. And I like the color play with the necklace and fun of having the beads when the shirt says “Pearls.” The crossbody is light and made it easy to walk.
Outcome: Lofted Settledness. The pants are tight, but I was still so happy! I will let them out though.
FRIDAY
What:
All day PJ style set is past season John Elliott (more all day PJs here, we keep adding more good ones)
Past season Tibi lace up loafer/mules. Saw these Rag & Bones IRL and thought they were very good. Splurge-worthy (and comfy) loafer sandal hybrid and more choices for you!
Old secondhand Raf Simons yellow tee with attached hood (and more hooded tees)
Gucci tote + Lemaire crossbody (above)
Oversized navy blazer around waist is old + secondhand Nomia (see below)
Why: Headed to Chicago. I like a set on a flight. Easy, comfy like PJs. You can change the tee and socks and wear it home, use the pieces on the trip, etc. I get very cold on planes + need layers. The yellow and blue is bright! But having so much of it and using the brown makes it feel playful and more relaxed somehow. Also the set is very textured. The ring is good in a situation like this — it adds friction to the prep/sport vibes and says this is fun.
Outcome: Lofted Settledness.
Friday night
What:
Junya Watanabe sequin graphic tee and more favorites for you
Nomia slit sleeve blazer, some options here
doing my favorite trick and taking just a phone and Trinity stick out, no purse … something about this I just love. Just - less.
Why:
Jim said this restaurant was nice but not too fancy. I thought that because it’s a graphic tee, even though it was sparkly, it would be fine. It was a later rez at a cool place. This skirt is simple and easy to pack. I wanted the blazer to add some big, top/skirt both slim. And white shoe was good with all that dark.
Outcome:
I liked! Not lofted, a little too much fitted for my taste, but it worked.
SATURDAY
day
What:
Ninety Percent tee (old) with ribbed neckline. The idea is a tee with some neck interest. I mean this would do it too.
Past seasons Dries shorts (comps here)
hub’s Grateful Dead hat (more good hats)
Why: Did a two hour walking architectural tour and then went to watch our friend pitch. This tee I got on sale at some point and this is something to look for in sale, I think — plain tees with a little interest. All together it made me feel ballgame-y without being in costume.
Outcome: Lofted Settledness.
sat night
What:
Old Jil Sander navy t shirt dress w/ruching - like this?
Tibi turtleneck (not many sizes left)— officially the hero of the trip
Why:
Met a friend of Jim’s and his partner for the first time; this was the “fancy dinner” of the trip. I love this dress; it’s super reliable. Ended up dumping the bag and taking the Trinity again! With the toe ring, the ruching, the earring — that was enough. I loved doubling up on the navy/texture by adding this turtleneck, which I ended up wearing inside the cold restaurant.
Outcome:
Felt great. Not Lofted, not especially fashion, but great. Sorry for the unfocused pic. It is a bad set up for photos + hard to get a decent one.
SUNDAY
What:
Same Rick skirt as Friday only I folded it over to hit at the knee. Here are knee lengths for you as well.
Talentless white tee (please note - I don’t know their sustainability practices) … Tibi’s version
Tibi navy sweater from sale (linked above)
Secondhand Gianvito Rossi thong sandals I just got at Castanet in Boston; this is the current version and it’s great; a very comfortable shoe that adds lightness to everything. (Some sizes on sale here.)
Marni extra wide vintage cuff — some good ones we found!
Why: I threw these shoes in instead of an extra pair of shorts and it was a good call. It was hot, and we went to brunch followed by a flea market. I did some work outside. These shoes are so flat and packable but they also held me with the back strap. My uniform tee made me feel like myself. This is also another example of my KSN (kitchen sink neutrals” theory. Hmmm. More on this.
Outcome: Lofted Settledness. Maybe my favorite of the week.
(Sunday later, to fly home … everything I wore on the way here but the tee above instead. Easy.)
OUTFIT PLANNING
This week: Working with things you bought or were gifted that have a little more of that summer vibe than you’re used to. A little market-y, etc. How do you make those feel like you?
Next week: Let’s re-hit out “neverworns” ala
, summer ed. Wear all the unworn items or get rid of them.Let’s get dressed.
XOXO,
Rachel
Notes:
I am using affiliate links, and I do not use them lightly. In fact here’s a whole post on it. Thank you for using these links to shop. Every little bit helps!
My Market editor Wendy and I are in limited, special, and really particular ways working with a select group of partners and accepting gifts in order to inform you better, especially around attainably priced brands and pieces. Here’s something on that.
We are also starting to get promo codes from brands, and here’s an updated list; be sure and check weekly before purchasing. I grew up shopping Filenes Basement. Your girl loves a discount:
CLOTHES
Callas Milano : Take 15% off with code HMS15
Heidi Merrick: Take 10% off with code HEYMRSSOLOMON10
Left on Friday: Take 10% off with code HMS10
Sanctuary: Take 15% off with code RS15
LUISAVIAROMA: Take 30% off full price items with this link and code LOVEX30 (excluding Adidas & Salomon)
Asher: Take 15% off with code RACHEL15
SHOES
Nomasei: Take 15% off with code HMS15
JEWELRY
AtPresent: Take 15% off with code HEYMRSSOLOMON15
BEAUTY
Lake & Skye: Take 15% off with code HMS15
Ursa Major: Take 20% off with code HEYMRSSOLOMON20
FRE Skincare: Take 25% off with code MRSSOLOMON
Rachel, dare I say this is one of my favourite weeks yet! Also you are the queen of title writing 😂🙌
Oh god I love this subtitle SO MUCH 🤣🤣🤣🤣🤣🤣