Never mind the homework or understanding shifting social structures — one of the toughest steps to feeling properly prepared for a new season of school, whatever form it might take, is dressing the part.

The majority of regulation uniforms, from boarding school blazers to insignia sweaters, quash any chance of personal style before you've even had a moment to mentally lay out your outfit.

But there are always ways to outsmart the institution, and we've picked out three fits for three very different back-to-school settings that'll let your individuality shine without you feeling out of place. But, if that isn't enough inspiration for you, our staff members have also weighed in and picked their back-to-school essentials.

Highsnobiety's guide on going back to school in style is below.

Homecoming

Logo Varsity Jacket

$415

Jacob & Co. x Highsnobiety

Buy at Highsnobiety

Hamer Sweatpants

$280

Dries Van Noten

Buy at Highsnobiety

Post-Modern Varsity Jacket

$1180

Off-White™ c/o Fashion Scholarship Fund

Buy at Highsnobiety
Belted Skirt

Belted Skirt

$246

Sean Suen

Buy at ssense

Homecoming queens live and die at the altar of athleisure, which means sweatpants are essential. Paired together with a varsity jacket, such as this one from Off-White™ or one from our Jacob & Co. collaboration, spell out support for your chosen house, while a Sean Suen skirt lets your cheerlead personal style. Bring all of those together and you have ticked every box when it comes to creating a homecoming outfit.

Boarding School

Striped Single-Breasted Wool Blazer

$4700

Prada

Buy at Farfetch

Crinkled Lambskin Jacket

$2150

Acne Studios

Buy at Farfetch

Shetland Wool And Cotton Crewneck Sweater

$1100

Marni

Buy at Marni
Stripe Tie

Stripe Tie

$165

Anna Sui

Buy at ssense

Boarding school is where the prep-style tree is watered, fed, and nurtured before fixing its roots in the adult's wardrobe. Blazers and ties are regulation. The crewneck sweater, coming courtesy of Marni, is a recess must. And, if you’re on the hunt for a blazer that adds some edge to your look, this crinkled lambskin Acne Studios style will do the trick.

Pre-School

Mohair Gilly Hat

$505

Dries Van Noten

Buy at Highsnobiety
Charm Necklace

Charm Necklace

$565

Acne Studios

Buy at Highsnobiety
Plush Scarf

Plush Scarf

$520

Marni

Buy at H.Lorenzo
Graphic Tee

Graphic Tee

$169

Kapital

Buy at H.Lorenzo

Fashion is still obsessed with dressing adults like giant babies. There’s no single form to this shrunken style, — Dries Van Noten is going all-out with a Cookie Monster-esque fluffy blue fabric, while Marni appears to have skinned my childhood teddy bear for its latest scarf, and Kapital is flying the flag for a style I am calling "children's pajamas-core."

Want to keep browsing? Head to the Highsnobiety Shop for more products that we love. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

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