Spotted: Preppy Chic On The Upper East Side

Maybe it’s the start of fall semester that invokes collegiate nostalgia of student uniforms and professorial tweed, or perhaps it’s simply the crisp autumn air – but there’s just something about fall that inspires us to channel prep school chic! And when it comes to preppy outfit inspiration, there is only one place to turn. Gossip Girl may be off the air, but we still look to Blair and Serena for their impeccable preppy style.

While we may not engage in Blair-like schemes, we sure loved everything she wore in the midst of them. So this season, embrace preppy your way, whether it’s in a preppy accessory or a thoroughly preppy ensemble meant for the Upper East Side. We’re eyeing classic prints like plaid and tartan, feminine details like necktie blouses and charming collars, and tailored pieces like sleek skirts and blazers. And don’t worry – you can dress with preppy style in a way that is polished and classy without being confused with a schoolgirl on her way to Calculus.

It’s impossible to talk about Blair’s style without mentioning her trademark accessory. She showed us time and again that adding a touch of preppy flair to an outfit is as easy as slipping on a headband over your tresses. In this outfit the preppy details abound, from the collared blouse, embellished gold bow, striped headband, and the Chanel-inspired jacket that always pulls together a classy outfit. 

Serena may not always look quite as perfectly put together and preppy as Blair, but this prep school gal knows how to look polished. This layered ensemble is perfect for strolling through Central Park in the fall with its warm autumn hues, but it’s the accessories that really elevate this outfit. From her metallic gold gloves to the menswear-inspired plaid tie worn loosely with that effortless Serena nonchalance, it’s clear that a preppy look comes together in the details.

Blair always expertly mixed classic prints, like this cropped tartan cape, into her fall ensembles for a perfectly layered preppy style. And we can’t help but adore her cute white beanie and matching gloves!

Stepping out as a college co-ed, Blair illustrates just how sophisticated the monochromatic trend can be in this olive green look. Choosing a top and skirt in two different olive green shades and layering a mustard button-up underneath keeps the monochromatic trend from overwhelming an outfit. And she expertly crosses the preppy finish line in her academic Oxford booties.

Team your favorite denim blues with fall riding boots, a classic white blouse and a pinstripe blazer for a polished fall outfit a la Serena. This sophisticated, tailored look is a great go-to outfit with just the right amount of preppiness for a more casual work lunch or weekend brunch with the girls.

Queen B makes even cold weather style incredibly chic with her statement coats! Here she looks every inch the American sweetheart in a quintessentially preppy color palette of navy blue, red, and white (it’s not just for Independence Day!) Keeping things ever thoughtfully styled, Blair accessorizes with a nautical headband, gloves and the perfect handbag.

Image Source: GG Fan Site

For preppy style that will add a dash of polish and sophistication to your fall wardrobe and have everyone confusing you for an Upper East Sider, shop our preppy attire.

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xo,
Ruche