Preppy Gets Weird: How to Wear the 2023 Subversive Preppy Look

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This isn’t your mother’s popped collar, Nantucket look. Spiced up tennis skirts, Instagram worthy socks and unexpected restyling of old favorites. We have nine inspo looks to get you in the *mood*.

As we know, preppy fashion typically includes clothing associated with Ivy League or private school attire, characterized by clean lines, classic cuts, and a focus on traditional, conservative styles. This style is often associated with a well-groomed and polished appearance.

Then what is the subversive preppy look? Is it the same as Dark Academia? Short answer, no. While DA tends to lean in heavily on the dark goth, Subversive Preppy doesn’t shy away from brights or even pastels. Instead, it intentionally takes traditional preppy fashion norms and disrupts the conservative image with edgier or countercultural elements.

Think Enid Sinclair, but if she were a massive fan of Panic at the Disco and Pleasure Venom.

Sound intriguing? Let’s let our Editors show how you can rock this style with nine inspirational looks.

#1 – CONTRASTING STYLES

Subversive preppy fashion often combines preppy staples like collared shirts, blazers, and loafers with elements from other subcultures, such as punk, grunge, or streetwear. We start with these awesome plaid pants by Collina Strada, that offer a little punk in the pattern, but full skater style in the baggy and wide leg. Prepping this up goes pretty easily when we start with great quality clothes – Mott & Bow’s super soft cashmere turtleneck, layered with rag & bone’s varsity-inspired v-neck sweater and a twill wrap coat from Sam Edelman finishes the layering. For accessories, we give a little more punk nod, with Zoe Lev’s diamond “nail” cuff ring and Satya’s double-pierce gold chain earring. Finally, we slide on a pair of G.H. Bass new season loafer.

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#2 – REBELLIOUS ACCESSORIES

Mixing “rebellious” with preppy is definitely one of the easiest ways to lean into this look. Accessories like leather jackets, studded belts, or combat boots added to preppy outfits give them an immediate rebellious edge. Case in point, Windsor’s sweet, baby blue plaid mini gets instant edge with a clashing heavy metal motorcycle jacket and some seriously stomping boots by Palladium. The juxtaposition continues when a silver, double-spiked choker is paired with a strand of classic pearls. All that’s left is to slide on a pair of hybrid punk-meets-sporty shades.

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#3 – POWERFUL PATTERN PLAY

Preppy and mixed print dressing aren’t just old friends, they share many traits that are easily interchangeable. Subversive prep can also dip into this field, taking on mix and matching both in print and materials. Here’s our fun take on this, where we pair J. McLaughlin’s handsome houndstooth trousers with a dopamine-inducing colorful sweater vest. Keeping in the same color family, we add Karl Lagerfeld’s poplin shirt, a pretty peony pink tie from Ties.com, with a tie pin to add just that luxe touch. Some neutral mary jane heels from M. Gemi keep the look grounded and we finish off with a flourish of burgundy-to-pink drop earrings from Kendra Scott.

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#4 – NON-TRADITIONAL COLORS

Experimenting with non-traditional or darker colors that deviate from the typical pastels and neutrals associated with preppy fashion. Of course, we still want to keep it prep without wandering too far into a gothic look. Our fit here shows how leaning into the darker side of prep can still keep the look firmly in preppy territory. Here we start with a tennis skirt with a twist by Lucky in Love. To this we add a striped beauty from Adam Lippes, with it’s oversized bow and gray and white silk. Forgo the expected knee high socks and go edgier with a pair of patterned black knee high and for the piece de resistance, a pair of dark and twisted platform loafers from Circus NY.

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#5 – SKEWED DETAILS

Adding off-center touches like asymmetrical cuts, patchwork pieces, or expected items with a touch of macabre twist can disrupt the polished preppy look. Our take on this starts with a fantastically skewed golf sweater from adidas, which pairs beautifully, in an off-kilter way, with Helmut Lang’s asymmetrical leather tennis skirt. A patchwork striped shirt from Lucky Brand continues giving that bit of edge. Finally for accessories we add the sweetest little rhinestone skulls from Baublebar and some loafers with an unexpected flatform heel.

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#6 – LAYERING

Layering is a key aspect of subversive preppy style. Mixing and matching different layers, such as oversized sweaters, hoodies, and blazers, can create a more eclectic and rebellious look. Our take starts with a cool cable knit and plaid check skirt set from b + ab. The set by itself is pretty great, but things get much more interesting when we add a graphic tee underneath and layer a sleeveless metallic puffer overtop. Keeping the visual interest going, we throw on these adorable daisy patterned tights from Target (a total steal at under ten dollars!) and finish off the look with a gorg mary jane platform heel by Matisse.

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#7 – VINTAGE MEETS THRIFT

Incorporating vintage or thrifted clothing items can add a unique and unconventional twist to the preppy style. Here’s a great example. We start with Windsor’s Preppy Plaid Blazer, that looks straight out of some amazing thrift store find. To this we add a vintage style Blondie tee and some rich cocoa colored faux leather joggers. Skip the expected loafers and slide on a pair of classic Vans high tops. Finally, we take one of the quintessential preppy jewelry pieces – the monogram necklace – and give it a darker edge in the shape of a black heart.

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#8 – GENDER FLUIDITY

Subversive preppy fashion often challenges traditional gender norms by mixing masculine and feminine elements in one outfit. Our fit starts with Diesel’s overlapping, meshy layered midi skirt and Ellen Tracy’s exaggerated button down, then juxtapose it with a chunky cropped cardigan from Smartwool. To this we add a gorgeous Gucci bees tie from their men’s collection and finish it off with M. Gemi’s stacked heel loafer.

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#9 – CULTURE CLUB

Incorporating elements from various subcultures, such as music, art, or politics, can also be part of the subversive preppy look. Here we start with a sweet tee with a strong message, courtesy of Fab Feminist. To this, we add a feast of fantastic plaids with Andersson Bell’s midi skirt. Finally, we accessorize with a layered necklace pair that includes Zoe Lev’s chunky, sterling chain, and Limoges’ leather choker with the option of your name scripted in sterling silver. And as we’ve seen all over this season, we pair the beloved ballet flat with some pristine white crews.

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Overall, the subversive preppy look is about taking the traditional preppy aesthetic and making it more eclectic, edgy, and individualistic. It’s a way of expressing one’s non-conformist style while playing with the contrast between the conservative and the rebellious.

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