These Preppy Outfits Are So Easy To Copy This Summer

It's time to try loafers with socks, dresses over shirts and checked suits.

Preppy outfits street style

by Harriet Davey |
Published on

When you think of the word 'preppy' you may automatically associate it with the constraints of school uniforms. The item checklist will include, but is not limited to: knee-high skirts, a sharp blazer, a jumper to go around your shoulders, a polo top, mini skirt and of course, loafers worn with socks. The spring/summer 2023 catwalks also had a strong undertone of preppy-related styling throughout many shows. The Row saw waistcoats (yes, they're sticking around) worn with done-up shirts, Tibi ticked off tailoring with blazers, Miu Miu delivered the pencil skirt. So yes, your initial thoughts of uniformed attire would indeed be correct. That is, however, until the street-stylers put their own spin on what the term preppy means in the fashion world, with some seriously enticing outfit ideas.

Taking the basics and giving them a twist, we've seen a striped shirt worn with a clashing flower-print tie complete with baseball cap and retro sneakers from Emili Sindlev. Tamu McPherson made a case for a checked skirt suit worn with white socks and ballerina pumps, and we're even seeing calf-length socks worn with kitten heels – yep, really. So shake off your opinion of preppy outfits as this is how to do it for 2023.

Wear Clashing Tailored Separates With Sporty Accessories

Street Style - Day 3 - Copenhagen Fashion Week Autumn/Winter 2023
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Emili Sindlev is one of those people to follow for a dopamine boost. With colourful clashing looks, the style insider never fails to uplift your feed. For Copenhagen Fashion Week, Emili took the preppy look into playful territory by clashing the striped blazer and shirt with a floral tie. It's the addition of the yellow leather mini, retro trainers and baseball cap that makes it feel so fresh this year. If you don't want to go quite as statement, you could just stick to a mini skirt, T-shirt and blazer worn with socks and trainers.

This single-breasted blazer will be your best friend for 3/4 of the year.

These zesty lemon shorts could be thrown over a swimsuit for poolside cocktails or paired with tailoring for city dinners.

Try Out A Polo Top

Preppy street style
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The uniform for the spring/summer 2023 Miu Miu? A polo top and a knee-length (or mini) skirt worn with white socks. This show-goer, however, took the look one step further by wearing the brand's slingback kitten heels. It's a look, for sure, and it's giving serious preppy vibes from all angles.

Boden's slim-fit polo shirts can be tucked into baggy jeans or a denim midi skirt.

Polo Ralph Lauren is your go-to when it comes to the preppy aesthetic and its polo shirts are unbeatable.

Add A Dress Over A Shirt

Preppy street style
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For a super easy way to try out the trend, take your favourite strap dress and a trusty shirt, then simply add the two together. This gives a slight preppy edge without being too OTT. Note: a pinafore-style dress will work best for this one.

With Nothing Underneath's range of shirting is legendary. This seersucker striped number would look lovely with a denim dungaree dress.

This lightweight pinafore dress will be a wardrobe staple during the spring and summer months.

The Knee-length Skirt Is Back

Preppy street style
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While Miu Miu made a case for the return of the micro mini, the label has introduced more wearable knee-length styles for next season. Model Tina Kunakey has made it feel more fashion than frumpy by opting for a matching jacket. We love the addition of grey socks.

This fit-and-flare cotton skirt might brush the knee but it's just as tantalising as a mini.

Sling A Jumper Over Your Shoulders

Preppy street style
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For that 'I'm with the team' school sports look, just add a jumper tied around your shoulders. This street-styler has gone for preppy underneath by wearing an oversized shirt layered with a waistcoat and tailored shorts. The cowgirl boots and statement accessories give it that 2023 flair we're looking for.

Everlane, The Alpaca Crew
Price: $113
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Everlane has some of the best knitwear on the high street.

The striped polo jumper is still the gift that keeps on giving when it comes to summer knitwear.

Wear A Suit With Ballerina Pumps

Preppy street style
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Tamu McPherson is a fan of tailored pieces, so we appreciate her take on this skirt suit worn with ballerinas (again, Miu Miu) and a zip-up cable-knit top. While we would have expected this outfit to be worn with loafers, trainers or boots, we're quite enjoying the less likely addition of the iconic pumps. Also, swap the sweater for a crop top and you've got a great going-out look or birthday outfit.

Aeyde's ballet pumps are a near-perfect iteration of the genre.

Halfway between a pump and a slipper, Vivi Venezia is another go-to for ballet flats.

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