Discover more from 5 Things You Should Buy
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.
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.
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:
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.
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?
Now go get digging in your closet. And in that box in your attic with your old school uniforms.
5 Things You Should Buy is a reader-supported publication AND a labor of LOVE! If you enjoyed this scroll, know that it A LOT of (very fun) work to bring it to you each week. Please consider upgrading to paid.
NOTE: I use affiliate links when applicable which means I may get a small commission from things you buy (no cost to you!) Thank you for supporting my work and trusting me with your shopping!