The Preppy Handbook: how to master the classic aesthetic

With shows like Succession and the Gossip Girl reboot gaining massive traction during the past couple of years, the internet is perpetually obsessed with “old money” aesthetics and the concept of “stealth wealth”.

The prep and old money aesthetics seem to go hand in hand as representations of the aspirational and unattainable lifestyles of the upper echelons. Fashion writer Alexandra Hildreth, in a TikTok posted on 12th April, explains that, back in the day, prep was characterised by the “socioeconomic and cultural signifier of essentially being white, upper middle class, or wealthy”.

As Alexandra goes on to say, the aesthetic was inextricably tangled with “inherent and learnt behaviours” correlated to that economic status, making it reactionary and exclusive.

View this post on Instagram

Instagram

To embed social media content, we use a third-party service which may collect data about your activity. Please review the details and accept the service to view this content.

Today prep is involved in a different cultural phenomenon: a subversion of the ideals it used to represent. Independent luxury brands like Chopova Lowena, Martine Rose, and Wales Bonner, but also industry titans like Miu Miu and Thom Browne, have co-opted the preppy aesthetic and turned it on its head, transforming it in a much more rugged, contemporary, and inclusive movement.

Tina Kunakey wears a striped zip-up jumper, straight blue jeans, and white tennis shoes.

Getty Images

While most of those brands focus on a more fluid and androgynous aesthetic, Miu Miu showed a girlier and nerdier side of prep for their SS23 runway, a side made of cashmere co-ords, frame bags, hosiery, and kitten heels.

View this post on Instagram

Instagram

To embed social media content, we use a third-party service which may collect data about your activity. Please review the details and accept the service to view this content.

In the words of Harper Bazaar’s Fashion News Director Rachel Tashjian, “Rather than reinforcing the lifestyle of prep and its trappings, [these brands] are swatting at them, playing with them, questioning them. Prep is back, and this time, it’s personal!”

If this new, rebellious prep tickles your fancy, here’s a handy guide on how to rock it.

1. Plaid and pleats

Yuzhen Wang wears a black leather jacket, a brown t-shirt, a midi plaid skirt with leather and metal belt details, and black biker ankle boots.

Getty Images

Absolute staples of the prep renaissance, plaid and pleats are ubiquitous in every prep brand’s collection. Pair your pleated skirt with rocker-style pieces to break away from the school uniform mold.

Ami

Ami De Coeur Wool Cardigan

At Balardi

£322.00 ~~£403.00~~

Delivery: £15.00

Buy it here

Fat Face

FatFace Leanna Black Leather Jacket

Delivery: £4.95

£199.00

FatFace

-30%

AllSaints

Womens Cactus Leather Dalby Desserto Biker Jacket, Size: UK 14/US 10 Black

Delivery: free

£223.30 ~~£319.00~~

AllSaints

-27%

The Garment

The Garment Brown

Delivery: £15.00

£387.00 ~~£533.00~~

Balardi

-30%

AllSaints

Leather Raul Leather Biker Jacket, Size: UK 14/US 10 Black

Delivery: free

£265.30 ~~£379.00~~

AllSaints

-43%

Emporio Armani

Zipped Blouson Jacket Grey

Delivery: £15.00

£281.00 ~~£493.00~~

Balardi

-30%

AllSaints

Womens Sheep Leather Balfern Leather Biker Jacket, Size: UK 16/US 12 Black

Delivery: free

£258.30 ~~£369.00~~

AllSaints

Fat Face

FatFace Tessa Black Leather Jacket

Delivery: £4.95

£199.00

FatFace

-30%

AllSaints

Polyester Saye Faux Fur Jacket, Size: XS Brown

Delivery: free

£167.30 ~~£239.00~~

AllSaints

More products

2. Statement coats

View this post on Instagram

Instagram

To embed social media content, we use a third-party service which may collect data about your activity. Please review the details and accept the service to view this content.

A statement coat should be structured but effortless, dandy but not pretentious. You are fancy, and therefore deserve the fanciest coat!

Saint Laurent

Nylon Cloak Coat

At Balardi

£1,389.00 ~~£2,945.00~~

Delivery: free

Buy it here

-53%

K-Way

Thersa Hooded Jacket Brown

Delivery: £15.00

£200.00 ~~£426.00~~

Balardi

-30%

AllSaints

Womens Cotton Aki Crossover Wide Leg Denim Jeans, Size: 28 White

Delivery: free

£104.30 ~~£149.00~~

AllSaints

BESTSELLER

Fat Face

FatFace Bianca Grey Longline Teddy Coat

Delivery: £4.95

£120.00

FatFace

-30%

AllSaints

Womens Polyurethane Cora High-Rise Faux Leggings, Size: UK 14/US 10 Black

Delivery: free

£97.30 ~~£139.00~~

AllSaints

Ariat

Womens Ballston Cardigan Top Long Sleeve in Sorrel Horse Plaid, Size X-Small, by Ariat

Delivery: free

£130.00

Ariat

-30%

BAM

Venture Fleece Gilet - Medium

Delivery: Delivery costs apply

£69.30 ~~£99.00~~

BAM

Nobody's Child

Brown Long Borg Duffle Coat

Delivery: free

£155.00

Nobody's Child

Fat Face

FatFace Harley Burgundy Red Longline Puffer Coat

Delivery: £4.95

£140.00

FatFace

More products

3. Chunky sweaters and cardigans

Diane Batoukina wears dark brown squared sunglasses, a pale blue cotton shirt, a white oversized pullover, a brown braided leather belt, baggy white linen pants, a camel brown handbag, and camel loafers.

Getty Images

Knitwear from a heritage brand like Ralph Lauren or Tommy Hilfiger is another prep staple. Pair your cable-knit sweaters and preppy cardigans with leather trousers or baggy jeans.

Wales Bonner

logo-appliqué bomber jacket - White

At FARFETCH

£1,653.00

Delivery: free

Buy it here

-24%

Polo Ralph Lauren

Plaited Cotton V Neck Sweater Black

Delivery: £15.00

£166.00 ~~£218.00~~

Balardi

-50%

Manuel Ritz

cropped cable-knit sweater - Black

Delivery: £10.00

£95.00 ~~£190.00~~

FARFETCH

-4%

Polo Ralph Lauren

Sweaters White

Delivery: £15.00

£193.00 ~~£202.00~~

Balardi

Charles & Keith

Apolline Textured Top-Zip Wallet Black

Delivery: £4.00

£35.00

Charles & Keith

-3%

Polo Ralph Lauren

Navy Blue Cotton Cable Knit Sweater

Delivery: £15.00

£128.00 ~~£132.00~~

Balardi

Charles & Keith

Apolline Textured Top-Zip Wallet Grey

Delivery: £4.00

£35.00

Charles & Keith

-12%

Liu Jo

Sweaters White

Delivery: £15.00

£125.00 ~~£142.00~~

Balardi

GANT

Women Stretch Cotton Cable Knit V-Neck Sweater (XXXL) FADED BRICK Pink

Delivery: Delivery costs apply

£125.00

GANT

More products

4. Shoes: from loafers to kitten heels

A Chopova Lowena model wears orange sunglasses, a printed button-up shirt, a metal bolo tie, a denim knee-lenght skirt, black and red socks, and black loafers.

Getty Images

Nothing says preppy like a classic pair of loafers: we recommend pairing them with thick white socks, to add a layer of ironic awkwardness. Speaking of awkwardness, Miu Miu SS23 made the nerdy girl with sheer tights and pointy kitten heels cool again.

Martine Rose

105mm extended-toe pumps - Pink

At FARFETCH

£394.00 ~~£666.00~~

Delivery: £10.00

Buy it here

Vagabond

Eyra - Womens Black Leather/embossed

Sold out

£130.00

Vagabond

Brittie - Womens Black Crinkled Patent Leather

Sold out

£135.00

Vagabond

Hunter

Womens Gloss Penny Loafers Blue

Sold out

£95.00

Hunter

Vagabond

Blanca - Womens Off White Suede

Sold out

£130.00

Vagabond

Russell & Bromley

FAIRYTALE Slingback Gem Kitten Heel Blue

Sold out

£275.00

Russell & Bromley

Miista

Mie snake-print leather sandals - Animal print - EU 35

Sold out

£280.00

The Outnet

Ted Baker

Womens Metallic Kitten Heel Sandals in White, Myloh, Leather

Sold out

£110.00

Ted Baker

Vagabond

Tilly - Womens Light Green Leather

Sold out

£130.00

Vagabond

More products

5. "Girly" accessories

View this post on Instagram

Instagram

To embed social media content, we use a third-party service which may collect data about your activity. Please review the details and accept the service to view this content.

Pairing your slacks, tweed blazers, and loafers with more feminine accessories is a great way to create a nice contrast. We recommend classic handbags, pearl jewellery, and sheer hosiery.

Miu Miu

mini Wander tote bag - Black

At FARFETCH

£1,520.00

Delivery: free

Buy it here

-22%

Jacquemus

Le Chiquito Handbag Black

Delivery: free

£482.00 ~~£618.00~~

Balardi

The Cambridge Satchel Company

The Daisy - Deep Purple Celtic Grain

Delivery: free

£200.00

Cambridge Satchel

-34%

BESTSELLER

MCM

Mcm Toni Handbag Blue

Delivery: £15.00

£385.00 ~~£582.00~~

Balardi

Russell & Bromley

CHORLTON TOTE Belted Structured Tote Black

Delivery: Delivery costs apply

£450.00

Russell & Bromley

-22%

Jacquemus

Le Petit Ovalo Shoulder Bag Brown

Delivery: free

£433.00 ~~£555.00~~

Balardi

Charles & Keith

Enola Canvas Two-Tone Elongated-Handle Bag Brown

Delivery: free

£79.00

Charles & Keith

-22%

Jacquemus

Le Petit Ovalo Shoulder Bag Yellow

Delivery: free

£433.00 ~~£555.00~~

Balardi

Charles & Keith

Enola Elongated-Handle Bag

Delivery: free

£79.00

Charles & Keith

More products

6. Statement glasses

View this post on Instagram

Instagram

To embed social media content, we use a third-party service which may collect data about your activity. Please review the details and accept the service to view this content.

A pair of wide-frame, rimmed glasses is another fantastic way to accessorise your preppy outfit.