14 Preppy Street Style Outfits That Put Blair Waldorf’s Headband to Shame

833 Shares
14 Preppy Street Style Outfits That Put Blair Waldorf’s Headband to Shame
14 Start slideshow
Photo: Christian Vierig/Getty Images.

As yet another long, hot summer comes to a close, so do the Spring/Summer 2018 tabs we bookmarked on our laptops for hot-weather wardrobe inspo. Sadly, this marks the end of rosé season—but we’re making up for the loss by putting something new on your radar.

Namely, fall fashion.

MORE: 7 Celebrities Who Fully Understand Food Is the Best Accessory

If you’re already feeling nostalgic about a summer Friday schedule, check yourself—because pretty soon, we’ll be replacing linen and bikinis with tweed and martinis. And that is way more important than leaving the office at 2 p.m. (Because you won’t be working—you’ll be werking.)

If you can think of something better than bright leaves and dark nails, it’d better be hot coffee and hotter ensembles—otherwise, we’re simply not listening.

MORE: Somehow, Elsa Hosk’s Outfit Has Us Daydreaming About Cooler Weather

Take a peek at the slideshow to see our latest inspo in the fashion department: preppy clothes that won’t make you look like you just walked off the Gossip Girl set. Because tailored layers look better when they’re edgy; perhaps they’ll even cure your end-of-summer blues.

0 Thoughts?
1 of 14
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Nina Schwichtenberg

Blogger Nina Schwichtenberg's ensemble comes on the cutting edge of trends like the baker boy hat and the oversized belt. The foundation of her outfit is clean, classic and coordinating—nothing short of preppy. Accessories elevate the look from schoolgirl to teacher by giving it high-fashion reinforcement.

Photo: Christian Vierig/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Alexandra Lapp

Blogger Alexandra Lapp's bold, tailored power suit could kill on its own, but it knows not to work harder than it has to—a classic houndstooth overcoat does the rest. Stark white accessories pull out understated milky tones from the rest of the ensemble, and bright red lips tie it all together.

Photo: Christian Vierig/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Unidentified Guest

This Fashion Week guest wears a plaid blazer, made inventive by black embroidery on the bodice and sleeves. Sleek sneakers and a graphic crossbody pouch serve urban edge to an otherwise preppy outfit, while metallic, square sunglasses deliver a futuristic touch.

Photo: Edward Berthelot/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Chelsea Leyland

DJ Chelsea Leyland breathes new life into Gossip Girl, pairing a micro-mini with matching over-the knee socks. Her dark ensemble is nothing if not chic, but accepts a little avant-garde support from a bright, '70s-inspired fur bag. Gucci's metallic loafer-style pumps draw the eye south and complement the gold in Leyland's coat.

Photo: Christian Vierig/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Guest

We might not know this Fashion Week guest's name, but we certainly want to. She expertly paired a (pink!) mid-length faux-fur overcoat with playful costume earrings and navy sock boots—essentially taking a page straight out of Fendi's haute couture Fashion Week 2018 lookbook.

Photo: NurPhoto/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Lisa Hahnbueck

If there's anything more fall-appropriate than a turtleneck sweater dress, it's a cobalt turtleneck sweater dress. Blogger Lisa Hahnbück's black-and-white accessories color block the outfit, and the tiniest blue details on both her bag and shoes tie the ensemble together.

Photo: Christian Vierig/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Layana Aguliar

Black and white dominate designer Layana Aguilar's ensemble, but it would be drab without the bold, playful pops of red delivered by her hat and lipstick. A beaded shoulder bag and patent-leather pumps elevate a preppy base to Fashion Week standards.

Photo: Matthew Sperzel/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Sonia Lyson

Influencer Sonia Lyson's outfit teeters on the fence between haute and whimsical. Purposefully clashing patterns, brightly colored jewels and hot pink nails complement each other just enough to land her a spot on our list.

Photo: Christian Vierig/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Michelle van Bijnen

Model Michelle van Bijnen upgrades her classic schoolgirl attire with leather accents, in the form of thigh-high Chelsea boots, a moto jacket and a Gucci crossbody. An understated pussycat bow and standout white collar bring focus to the bodice, where all the action takes place.

Photo: Melodie Jeng/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Gitta Banko

Blogger Gitta Banko turns an average pair of jeans into the perfect complement for her silky champagne slip dress and leopard-print blazer. Her white Chanel coordinates flawlessly with a pair of sneakers, which, expectedly, change the tone of her outfit from super-feminine to street-friendly.

Photo: Christian Vierig/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Caroline Daur

Blogger Caroline Daur's coordinated patterned suit is enhanced by an oversized belt, which not only elongates her legs, but also gives the pant an unexpected edge. A two-toned orange handbag affords the ensemble even more excitement.

Photo: Jeremy Moeller/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Vanessa Fuchs

Model Vanessa Fuchs' ultra-feminine style shines in an intentionally uncoordinated pink suit. Her color palette is a major upgrade from monochrome, and when paired with black accessories, the outfit becomes contemporary. Enormous jewels are a playful jaw-framing accent.

Photo: Christian Vierig/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Landiana Cerciu

Landiana Cerciu, model and vice president of Feeric Fashion Week, knows her way around the color wheel. She coordinates opposing colors for an appealing tonal aesthetic and mixes feminine and masculine elements in an unexpectedly successful collaboration.

Photo: Edward Berthelot/Getty Images.
14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Joanna Horodynska

Model Joanna Horodynska takes an unconventional approach to the biker short trend, pairing hers with tweed flats and a clashing plaid jacket. A third pattern, in the form of leopard print, confirms intentionality, and seamlessly takes the outfit to haute status. A waist-cinching belt and coordinating bucket bag complete the look.

Photo: Christian Vierig/Getty Images.

Next slideshow starts in 10s

The 9 Best Face Masks for All Types of Oily Skin (Yes, Even Yours!)

The 9 Best Face Masks for All
Types of Oily Skin (Yes, Even Yours!)
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Nina Schwichtenberg
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Alexandra Lapp
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Unidentified Guest
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Chelsea Leyland
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Guest
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Lisa Hahnbueck
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Layana Aguliar
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Sonia Lyson
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Michelle van Bijnen
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Gitta Banko
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Caroline Daur
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Vanessa Fuchs
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Landiana Cerciu
  • 14 Preppy Street Style Outfits that Put Blair Waldorf's Headband to Shame | STYLECASTER | Joanna Horodynska

Promoted Stories

share