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.
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.
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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.
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
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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.
Closed
X-Lent tapered jeans - Black
-32%
Infinity Leather
Womens Classic Brando Biker Jacket-Loughton - Green Lamb Leather - Size 10 UK
£84.99
£124.99
Secret Sales
-15%
Infinity Leather
Womens Black Shearling Sheepskin Aviator Jacket-Kiev - Size 24 UK
£304.99
£359.99
Secret Sales
-51%
Ganni
Duchesse Nylon Fitted Jacket Black
£245.00
£495.00
Labels
-77%
Elle
Womens Annette Leather Jacket in Black - Size 12 UK
£69.98
£299.99
Secret Sales
-30%
Fat Face
FatFace Leanna Black Leather Jacket
£139.00
£199.00
FatFace
-29%
Infinity Leather
Womens Black Biker Jacket-Tamale - Size 10 UK
£120.99
£169.99
Secret Sales
A statement coat should be structured but effortless, dandy but not pretentious. You are fancy, and therefore deserve the fanciest coat!
-37%
Michael Michael Kors
hooded puffer coat - Green
£152.00
£243.00
FARFETCH
Fat Face
FatFace Harley Burgundy Red Longline Puffer Coat
£140.00
FatFace
-60%
AllSaints
Wool Sellma Double Breasted Coat, Size: UK 14/US 10 Brown
£159.20
£399.00
AllSaints
-71%
Dare 2B
Dare 2B Womens/Ladies Striking III Long Length Padded Jacket (Orion Grey/Orion) - Size 10 UK
£58.39
£200.00
Secret Sales
-30%
Fat Face
FatFace Bianca Grey Longline Teddy Coat
£84.00
£120.00
FatFace
-60%
Elle
Womens Emma Festival Mac in Sand - Size 18 UK Beige
£59.99
£149.00
Secret Sales
-30%
Michael Michael Kors
leopard-print puffer coat - Black
£197.00
£281.00
FARFETCH
-26%
Joules
Womens Elbridge Jacket in Black Recycled Material - Size 16 UK
£117.08
£159.00
Secret Sales
3. Chunky sweaters and cardigans
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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)
-40%
Varley
Camello cable-knit half-zip sweater Beige
£90.00
£150.00
Mytheresa
-10%
Polo Ralph Lauren
crew-neck cable-knit sweater - Pink
£190.00
£212.00
FARFETCH
-20%
Polo Ralph Lauren
Cable-knit cotton sweater Pink
£152.00
£190.00
Mytheresa
Liu Jo
embellished openwork-knit sweater - Grey
£165.00
FARFETCH
Polo Ralph Lauren
Cable-knit cashmere and wool sweater White
£200.00
Mytheresa
Polo Ralph Lauren
cable-knit sweater - Pink
£189.00
FARFETCH
Polo Ralph Lauren
Cable-knit cotton sweater Blue
£200.00
Mytheresa
-14%
Polo Ralph Lauren
cable-knit V-neck sweater - Neutrals Beige
£194.00
£225.00
FARFETCH
4. Shoes: from loafers to kitten heels
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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
90mm square-toe pumps - Yellow
Vagabond
Eyra - Womens Black Leather/embossed
£130.00
Vagabond
Vagabond
Brittie - Womens Black Crinkled Patent Leather
£135.00
Vagabond
Hunter
Womens Gloss Penny Loafers Blue
£95.00
Hunter
Vagabond
Blanca - Womens Off White Suede
£130.00
Vagabond
Russell & Bromley
FAIRYTALE Slingback Gem Kitten Heel Blue
£275.00
Russell & Bromley
Miista
Mie snake-print leather sandals - Animal print - EU 35
£280.00
The Outnet
Ted Baker
Womens Metallic Kitten Heel Sandals in White, Myloh, Leather
£110.00
Ted Baker
Vagabond
Tilly - Womens Light Green Leather
£130.00
Vagabond
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.
-30%
The Cambridge Satchel Company
The Daisy - Deep Purple Celtic Grain
£140.00
£200.00
Cambridge Satchel
-10%
Prada
2000-2025 Vitello Daino Frame Convertible Tote satchel - Black
£530.00
£590.00
FARFETCH
Russell & Bromley
CHORLTON TOTE Belted Structured Tote Black
£450.00
Russell & Bromley
-20%
The Cambridge Satchel Company
The Mini Sophie - Metallic Emerald Green
£420.00
£525.00
Cambridge Satchel
Russell & Bromley
SUTTON LARGE Large Oval Shoulder Bag Black
£350.00
Russell & Bromley
Anya Hindmarch
Maud clutch bag - Silver
£978.00
FARFETCH
-43%
Calvin Klein
BAGS - Handbags on YOOX.COM Black
£85.00
£148.00
Yoox.com
-30%
Dior
2007 Large Calfskin My Dior Frame handbag - White
£484.00
£692.00
FARFETCH
A pair of wide-frame, rimmed glasses is another fantastic way to accessorise your preppy outfit.
Face à Face
square-frame glasses - Blue
£200.00
FARFETCH
Charles & Keith
Renee Recycled Acetate Butterfly Sunglasses Black
£75.00
Charles & Keith
Miu Miu Eyewear
tortoiseshell-effect square glasses - Brown
£170.00
FARFETCH
-53%
Sandro
Sandro Womens Optical Frame SD4008 989 49 - Silver Stainless Steel (archived) - One Size
£87.00
£186.00
Secret Sales
-14%
Prada
square-frame glasses - Pink
£199.00
£231.00
FARFETCH
Gigi Studios
square-frame glasses - Brown
£152.00
FARFETCH
Dior
1970s ombré butterfly-frame glasses - Yellow
£197.00
FARFETCH
Prada
square-frame glasses - Black
£153.00
FARFETCH
