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.

Valentino Garavani

Bowshire polished leather loafers

At Mytheresa

£528.00 ~~£880.00~~

Delivery: Delivery costs apply

Buy it here

-30%

AllSaints

Womens Polyurethane Dalby Slim Fit Faux Biker Jacket, Size: XS Black

Delivery: free

£174.00 ~~£249.00~~

AllSaints

-20%

Rotate

Leather biker jacket Black

Delivery: Delivery costs apply

£496.00 ~~£620.00~~

Mytheresa

-50%

AllSaints

Womens Leather Daylen Oversized Leather Biker Jacket, Size: L Black

Delivery: free

£199.00 ~~£399.00~~

AllSaints

-15%

Infinity Leather

Womens Black Shearling Sheepskin Aviator Jacket-Kiev - Size 22 UK

Delivery: £2.99

£304.99 ~~£359.99~~

Secret Sales

AllSaints

Leather Clo Pleated Leather Jacket, Size: UK 16/US 12 Black

Delivery: free

£349.00

AllSaints

-32%

Infinity Leather

Womens Classic Brando Biker Jacket-Loughton - Green Lamb Leather - Size 10 UK

Delivery: £2.99

£84.99 ~~£124.99~~

Secret Sales

AllSaints

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

Delivery: free

£319.00

AllSaints

-29%

Infinity Leather

Womens Black Biker Jacket-Tamale - Size 18 UK

Delivery: £2.99

£120.99 ~~£169.99~~

Secret Sales

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

Suede trench coat

At Mytheresa

£6,115.00

Delivery: Delivery costs apply

Buy it here

Fat Face

FatFace Harley Burgundy Red Longline Puffer Coat

Delivery: £4.95

£140.00

FatFace

AllSaints

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

Delivery: free

£149.00

AllSaints

Fat Face FatFace Bianca Grey Longline Teddy Coat

-30%

BESTSELLER

Fat Face

FatFace Bianca Grey Longline Teddy Coat

Delivery: £4.95

£84.00 ~~£120.00~~

FatFace

AllSaints

Cotton/Modal Raffi Slim Fit Leggings, Size: XS Black

Delivery: free

£59.00

AllSaints

-30%

Fat Face

FatFace Aubrey Blush Pink Structured Coat

Delivery: £4.95

£112.00 ~~£160.00~~

FatFace

-50%

AllSaints

Wool Sellma Double Breasted Coat, Size: UK 14/US 10 Brown

Delivery: free

£199.00 ~~£399.00~~

AllSaints

-50%

GANT

Women Waxed Cotton Car Coat (XXL) DARK MOSS GREEN

Delivery: Delivery costs apply

£175.00 ~~£350.00~~

GANT

-40%

AllSaints

Womens Wool Sidney Wool Cashmere Blend Tailored Coat, Size: UK 14/US 10 Black

Delivery: free

£197.00 ~~£329.00~~

AllSaints

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

Adidas X Wales Bonner X Wales Bonner Stripe-intarsia Knit Cardigan - Red - S (UK8-10 / S)

At Harvey Nichols

£254.00

Delivery: £7.50

Buy it here

-40%

Varley

Camello cable-knit half-zip sweater Beige

Delivery: Delivery costs apply

£90.00 ~~£150.00~~

Mytheresa

-40%

Sandro

Sleeveless cable knit sweater Pink

Delivery: free

£125.40 ~~£209.00~~

Sandro

Polo Ralph Lauren

Cable-knit cotton sweater Blue

Delivery: Delivery costs apply

£200.00

Mytheresa

-10%

Polo Ralph Lauren

Cable Knit Jumper Pink

Delivery: Delivery costs apply

£176.18 ~~£195.75~~

Miinto

Polo Ralph Lauren

Cable-knit cotton sweater White

Delivery: Delivery costs apply

£200.00

Mytheresa

GANT

Women Stretch Cotton Cable Knit Crew Neck Sweater (XXXL) EGGSHELL White

Delivery: Delivery costs apply

£125.00

GANT

-20%

Polo Ralph Lauren

Pony cable-knit wool and cashmere sweater White

Delivery: Delivery costs apply

£180.00 ~~£225.00~~

Mytheresa

Bloch

BLOCH Ladies Bianca 3/4 Sleeve Sweater, Grey Marle

Delivery: £4.95

£39.00

BLOCH

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

Lace-Up Ankle Boots - Unisex - Other Fibres/Leather/Rubber/Goose Down

At Browns

£230.00

Delivery: £5.00

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

Miu Wander matelasse leather shoulder bag

At Mytheresa

£2,100.00

Delivery: Delivery costs apply

Buy it here

Russell & Bromley

CHORLTON TOTE Belted Structured Tote Black

Delivery: Delivery costs apply

£450.00

Russell & Bromley

-12%

Furla

BAGS - Handbags on YOOX.COM Silver

Delivery: £9.00

£165.00 ~~£188.00~~

Yoox.com

Vivienne Westwood

Granny Frame leather tote bag Black

Delivery: Delivery costs apply

£255.00

Mytheresa

Laura di Maggio

BAGS - Handbags on YOOX.COM Brown

Delivery: £9.00

£150.00

Yoox.com

The Cambridge Satchel Company

The Mini Sophie - Cloud Blue Calf Grain

Delivery: free

£415.00

Cambridge Satchel

-13%

Ermanno Scervino

BAGS - Handbags on YOOX.COM Silver

Delivery: £9.00

£98.00 ~~£113.00~~

Yoox.com

Russell & Bromley

SUTTON LARGE Large Oval Shoulder Bag Black

Delivery: Delivery costs apply

£350.00

Russell & Bromley

-20%

Furla

BAGS - Handbags on YOOX.COM Blue

Delivery: £9.00

£168.00 ~~£210.00~~

Yoox.com

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.