Take the Prep Out Of Your Step

How to un-yuppie five fantastic classics.

People always tell me I’m preppy. It makes me wrinkle my nose a little. It’s not untrue, but I’d like to say I’m discerning even when being categorized. Is it also true that I bought a uniform of navy cardigan, knee highs and loafers with my Bat Mitzvah money? Yes. (At least I’m consistent!) But the thing is, an actual uniform makes me feel stifled and it’s the mixing it all up that allows these classic pieces I love to live beyond their tropes. I never want to walk down the street and feel like I’m in a costume or a brand’s advertisement. So this week, we are taking five pieces in my closet that are extremely PREPPY capital P, and making them wearable beyond the “club,” because let’s get real, I’m definitely not a member.

After trying on just about my entire closet, the biggest takeaway you will see today, is that these classic pieces need to be paired with specialty items. For the most part, a classic jean just won’t cut it. Today is going to be filled with wacky and wild ideas because that’s actually what these pieces need. Taken too minimally, they bizarrely become stuffy. Secondly, I’ve found as a general rule, heavier accessories - chunky boots, bags with silver chains and hardware, buckles, etc. seem to balance all of this pretty well. Pleasantly, it made accessories I find harder to wear, easier! Are you confused yet? You’ll see as we go.

The Dinner Jacket

Ahhh, the age old Brooks Bros classic (though this one is Polo). Did I steal this out of the hostess closet at the Union Club? Maybe! JK JK. But maaaaybe.

The easiest way to take the prep out, I’ve found through all of this, is to add black. Black is NOT a preppy color. Too harsh. Too un-collegiate. So the first thing I did when prepping (no pun intended!) this newsletter was throw this blazer on with my black parachute pants. Done! Polo dinner jacket, Kallmeyer t-shirt, The Row pants and shoes. These are fun pants (though I’d probably hem them at least a half foot) and the shoes are an anomaly but I also love these mesh guys.

Quite possibly my favorite outfit in this roundup. Who wants to go for a walk aorund the reservoir? Polo dinner jacket, Kallmeyer t-shirt, Polo sweatpants, Loewe x On Running sneakers.

For evening! The Polo dinner jacket with a black lace trimmed camisole by Rohe, this one is also pretty, if your size is sold out, this one is so pretty too. An old black crepe skirt, this one looks identical. Prada d’orsay pumps. Also love these though they seem to be perpetually sold out. Maybe I’ll inquire for us.

With distressed jeans and combat boots to take any uptown-i-ness out of the scenario. With an XL Loro Piana silk blouse snagged on TRR (here (size up) and here (size down) look like great alts), Dissh jeans (more on these in two weeks), The Row combat boots (also love these!)

The kilt

One of my all time favorite pieces of clothing. A plaid pleated skirt. Now, this is a style I have not trusted myself to wear since I was very young and shopped in the school uniform section by choice (even though I went to public school.) But this whole newsletter this week started with this particular Comme des Garçons kilt. I figured a) if there is any plaid skirt that can be made cool, it’s this one. And I just kind of felt ready to give this style a go again, it calls to me so hard.

This outfit brings me boundless joy. The real trick here, is that the sweater is not a classic shape. It’s a little drippy, without any classic, ribbed detailing on the neck or hemline. That plus the knee-high combat boots and chain bag toughen this up a bit. Comme des Garcons kilt, an old sweater with no tag but the idea here is wide hem. This Lands End guy looks perfect. Or this super luxe number from Lisa Yang, Ann Demulemester boots. A smattering of sizing here and here. And heavily discounted here.…more on boots next week, but these are also awesome. Prada re-edition bag.

With an oversized black blazer. Super important that I chose a blazer with minimal detailing and long clean lines. Nothing that feels tight to the body, could be seen as sweet or too “classic”. With a simple slide shoe and my studded bag, it’s all balanced, and perfectly grown up. The Row blazer (how cool is this Cos version that gives the same deconstructed back detail vibes), Alaia demi lune bag, Manolo Blahnik slides

The back!

With a non-matching knit. Now a sweater can veer this skirt into extremely traditional territory, so avoid a fisherman or anything too classic. This sweater is purple/white/navy marled so feels just the right amount of off. High Sport sweater, CDG kilt.

Oh man do I love mixing my plaids. Technically the coat is a herringbone but I love the look of these together. It’s a lot. Just enough to not focus on the skirt alone. The insane gold boots also don’t hurt. Officine Generale coat, a recent purchase in Paris. Madewell oversized t-shirt, CDG kilt, Khaite boots.

Just a better detail shot of the pleats. Swoon!

Funny thing is. You’re going to start seeing plaid skirts everywhere now! From left: CDG, Chopova Lowena, Lands End (!!!), Thom Browne, Mango, Scotland Kilt, Sea NY

Khaki Pants

Honestly, so challenging. I feel like such a dufus in khaki. Such a great color in theory. In practice so hard to balance. So much so that I don’t even have a pair anymore. Just these khaki colored corduroy pants which are a perfectly suitable (if not even more challenging!) placeholder. Remember last year when I swore off corduroy? I spent so much time trying on different pairs, determined to find one that worked. I still stand by my statement that they are not the most flattering fabric. But these were what I ended up with after my hunt last spring. After putting all these looks together, I’m starting to think maybe I’m warming on cord, and going to consider a more everyday pair as well. Maybe. Anyway, I find khaki to be an extremely hard pant to pair shoes with. I think they look great with sandals, when the femininity of an ankle or foot can ground the look. But it’s getting cold outside, and it’s a pant I want to wear in the fall. It was not impossible, but took a while to figure it out. Here’s where we landed:

Beige on beige. Quiet luxury is not equal to preppy, let me remind you! Paired back to Asics, this is probably what I’ll be wearing next time you see me at the library. Lisa Yang sweater, Loro Piana corduroy pants, but get these from the Gap, so good!, Asics sneakers.

Making them into cocktail wear was easier than expected. But I didn’t want to fall into the 2008 J.Crew trope of khaki paired with sparkle, that felt too dated. So paired these with my tuxedo jacket, strappy sandals and some big hoops! An old tuxedo jacket. Can I recommend the the Me + Em tux? It’s fantastic. Kate Young x Monica Vinader hoops, Manolo sandals. These are probably the most current iteration? And I’ll always love the Nudist.

I have had this belt for over a year and never worn it. I’m so happy I figured it out! It’s giving me St. Marks Place circa Felicity. Agnes B. cardigan, our favorite Nili Lotan tank, more sizes here, Khaite belt, Loro Piana khakis but again, try these.

Uptown Art Fair mom. Something for the Minnesota crew out there. Alix of Bohemia blouse, Loro Piana khakis, Manolo Blahnik ballerinas (I also love these as you know…size up!)

Penny Loafers (like with an actual penny)

Kind of a no brainer item at this point, but I couldn’t not include loafers so just just leaned into the prettiness. They’re listed on the cover of The Preppy Handbook for crying out loud! Did you know you can actually put a penny in your loafer!? It’s true. What I have found about un-prepping them was so specific to each outfit that I encourage you to just read the captions.

Tod’s loafers (though there are a million great pair out there) paired with my old Khaite Zebra pants (wow who knew these were going to become such a staple!?) If you’re a size 4, here! These are a great alternate. CDG blazer, grey Dissh t-shirt. This is obiously about the wildcard factor of the pants, balancing the shoe. But the jacket is also collarless and slightly cropped which takes it out of “traditional tailoring” vibes.

The same cropped CDG jacket, B Sides Eshel jeans, Tod’s loafers. Prada re-edition bag. This is all about that frayed hem balancing out the classicness of the shoe. And a jacket with no lapel. I think a lapeled jacket would make this too uniform-like to make our point. 

Promise I’m happier than I look, though it’s all a roller coaster these days isn’t it? Ok, so this look is more than meets the eye. Because usually, to take the prep OUT, I would advise against white jeans. But these are a super duper baggy white jean. And then a plaid shirt…also tricky, but this is a washed out, almost western style flannel, not to be confused with a dressier suit-y plaid shirt. It all just kind of works in an off way. Polo RL shirt, Citizens of Humanity jeans, Tod’s loafers

Turn your LBD into daywear! Attersee dress. AG Jeans t-shirt layered underneath which they horrifyingly discontinued! (bring it back AG!) This is the best alternate I’ve found though its more expensive. :( Tod’s loafers, Wayfarers

With a ‘could never be confused as preppy’ leather jacket by Malene Birger, Attersee black silk pants, Tod’s loafers

The Cableknit Cardigan

This one was TOUGH! Basically, what I’ve determined is, a cable knit cardigan can’t really be paired with jeans if we are taking it out of the neighborhood. Too one dimensional. So once again, just brought in my wackiest pants and then treated the sweater as a pajama top for the real world. How did I do?

White + Warren cardigan, Lauren Manoogian Grunge pants, Vans sneakers

White + Warren cardigan, Khaite pants (but again, these), Aeyde Mary Janes.

White + Warren cardigan, Attersee silk cocktail pants, Dissh t-shirt, Loewe x On sneakers, Savette bag

 White+Warren sweater. Orange tank **for the readers out there about styling orange!!**, Tory Burch maxi skirt (90s vibes), here is another cute one. And don’t forget about Paco Rabanne on The Outnet, always a great resource. Prada re-edition bag. Birkenstocks

For evening (even though I just woke up and you can really tell in this picture!) with our Black Maria McManus pants (or whatever cropped black pants you have!), fishnets!!!!! and patent leather pumps. These are an old pair I scored at the Dior outlet at Woodbury Commons :) but these are also fab. 

Now go get digging in your closet. And in that box in your attic with your old school uniforms.

Yours TRULY,

Becky

At the end of the day, who am I to fight my true calling…I actually love this look: sweater, pants and loafers harmony, and will probably be wearing it next time I see you.

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