We’ve all seen the pictures.
Princess Diana swanning around looking cool and casual in cycling shorts and a large oversized sweater, usually featuring an American collegiate logo. The good news is that whether you’re thrifting or buying new, there are plenty of options around so you may just find yourself spoilt for choice when you’re following her lead.
Whether it’s a Harvard University emblem or a brand’s logo, we’re looking for letterman font, sporty references and a large print or embroidery in a contrast colour for styles that live up to the preppy rep. Any colour could work, from grey, to burgundy, to navy, just make sure the palette is complimentary rather than jarring.
Go for an oversized silhouette in a sweatshirt, hoodie, or ¼ zip, and pair with sporty shorts, from a retro running style to a skin-tight cycling design. If it’s a touch too cold for bare legs, a pair of leggings or relaxed straight leg jeans will keep up the laid-back aesthetic, and always finish the look with sports socks and dad sneakers - any from New Balance or Axel Arigato would do the trick.
If you’re going for a more smart-casual aesthetic, then you could tuck the sweatshirt in and layer beneath a boxy blazer à la Hailey Bieber, and pair with chunky loafers or a pair of cool kitten heels. To up the undercover-celebrity ante, accessorize with sunglasses and a baseball cap.
We’ve researched the best on the market that will have you looking like an Ivy League graduate in no time.
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Sporty & Rich Wimbledon Printed Cotton-Jersey Sweatshirt
As you might guess from the name, Sporty & Rich’ aesthetic is preppy through and through. With a logo on the front and back, you’ll be covered from all angles.
Buy now £140.00, Net-A-Porter
Fiorucci Sport Logo Sweat
Since designer Daniel W Fletcher took the reins at Fiorucci, it’s gone from strength to strength. Equal parts stylish and comfy, this sweat is oozing with varsity style.
Buy now £139.00, Fiorucci
Beyond Retro Nascar Printed Sweatshirt
If you like to wear one-of-a-kind pieces, then thrifting your sweatshirt is the best bet. London-based vintage store Beyond Retro has a great selection, but this Nascar racing design takes first place for us.
Buy now £30.00, Beyond Retro
Lamarel Swiss Sport Attire Navy Sweater
You may have seen Lamarel’s classic tracksuits gracing your IG feed thanks to the label’s influencer fan club, but if not, you’re in for a treat. The Swiss brand offers an amazing collection of high-quality, unisex, vintage-looking pieces at an accessible price point.
Our favourite is this navy sweatshirt that would look best worn with the matching shorts.
Buy now £78.90, Lamarel
Tommy Jeans Prep Oversized Sweatshirt
When it comes to varsity style, Tommy Jeans is a surfire win. From the bold red logo to the relaxed fit, the vibe of this sweatshirt fits the bill to a tee.
Buy now £95.00, Tommy Jeans
Polo Sport Fleece Sweatshirt
For all things quintessentially American, Polo Sport is a safe bet. This fleece backed cotton sweatshirt will keep you cosy on the chillier days - just size up if you’re after an oversized look.
Buy now £116.00, Polo Sport
Axel Arigato Arigato University Sweatshirt
Whilst Axel Arigato may not be a legit university, the Scandi brand’s design ticks all of the collegiate boxes. Crafted using a super soft organic cotton, it’s oversized, and features a contrast logo and relaxed drop shoulder. You’ll never want to take it off.
Buy now £160.00, Axel Arigato
Anine Bing Ramona Sweatshirt University London
One for the anglophiles out there, Anine Bing’s London sweatshirt will allow you to proudly show off your love for the capital. A more structured option, it would work well for a more smart-casual vibe.
Buy now £195.00, Anine Bing
Rowing Blazers X Firstport Greenwich Tennis Crewneck
All of Rowing Blazers designs have a preppy vibe, and we’re fully here for it. This sweatshirt, from the brand’s collab with Firstport, is designed using 100 per cent organic cotton, and has the 80s sporty mood we’re looking for.
Buy now £100.00, Rowing Blazers
Goldsmith Vintage US Olympics Team Blue Sweatshirt
Shopping vintage is a great option for a collegiate sweatshirt. This style from Goldsmith Vintage will have you feeling like the champion you are, and if this one’s not for you, there are plenty of others to tickle your fancy.
Buy now £44.95, Goldsmith Vintage
SOONTOBEANNOUNCED Essentials Logo Sweatshirt
For quality essentials with a contemporary design twist, Istanbul-based brand SOONTOBEANNOUNCED is the place to go. Our favourite is the label’s vintage-inspired essentials sweatshirt, which is offered in six colourways.
Buy now £103.00, SOONTOBEANNOUNCED
