19 Preppy Pieces of Clothing Even Blair Waldorf Would be Proud of

The 24 hours in which Brooklyn Nine-Nine was cancelled and then renewed were possibly the most nerve-racking of my life. I mean, Jake Peralta is my dream man — how can you not be in love with a man who forgets about solving a murder case because he’s getting too into singing The Backstreet Boys? I’ll get to the Blair Waldorf section of this article right after this video.

That’s what I thought. Now, as I wait for season six, I need something to fill up my time. And, aimlessly scrolling through Netflix I discovered my high school obsession and the reason my wardrobe looks the way it does – Gossip Girl.

So, when rewatching it, I remembered just how much I loved Blair Waldorf – I still have a collection of headbands that I refuse to throw out – and her wardrobe. Inspired by her, I’ve decided to bring out some of the preppy style pieces that have been lying dormant in my closet…

Blair Waldorf
Photo Credit: Instagram User @taylorwster


Steal Blair Waldorf’s style

Here are 19 pieces of clothing that even Blair Waldorf would be proud of – some a little over the top, some just lending a hint of prep, but all that could have ended up in the show when there’s an eventual reboot.

Frills were aplenty in Blair Waldorf’s wardrobe. Let’s not forget her 18th birthday outfit, where she wore a halter-neck top that was entirely made out of frills. Here’s a more laid back option that still leans into the frills, and would be perfect for a breezy summer’s day.

Off Shoulder Top with Ruffle Detail, £32.00, ASOS asos.com


Looking for a cute co-ord outfit that 2015 Taylor Swift would be proud of (we’re talking pre-bleached hair here)? Topshop has your back, with a feminine, flirty outfit that would definitely appear in Miss Swift’s wardrobe.

Boucle Cropped Jacket, £59.00 Topshop topshop.com

Boucle Skirt, £36.00 Topshop topshop.com


There’s nothing like wearing your heart on your sleeve…or your initials in your hair? This embroidered velvet hairclip can tie together any outfit – and the black keeps it from being that bit too twee.

Embroidered Velvet Hairclip, £65.00 LELET NY at net-a-porter.com


Caroline Constas is known for it’s beautiful, feminine dresses. Frills and bows aplenty, this dress is a little more laid back – but just as eye-catching in its sunny canary yellow. This may be the perfect picnic dress.

The Gretta Dress, £374.38 Caroline Constas carolineconstas.com



A black handbag is a staple in any woman’s wardrobe. But, with so many variations out there, this Kate Spade one is the perfect option to add a little kitsch and fun into your bag collection.

Cat’s Meow Cat Lottie, £358.00 Kate Spade katespade.co.uk


Like the wise Beyonce once said, if you like it then you should’ve put a bow on it. I may have definitely changed a word there, but the sentiment rings true. These Ted Baker heels are a perfect way to add a little bit of prep to a wardrobe staple.

Bow Detail Heeled Sandals, £98.00 Ted Baker tedbaker.com


You can never go wrong with a pair of cigarette trousers – there’s a reason Audrey Hepburn favoured them so much. Go for a bold colour to add a little pep in your step.

Skinny Trousers, £69.00 & Other Stories stories.com


Bring the schoolgirl plaid back with a decidedly more grown-up look. Pair the jumpsuit with a white crop and sneakers for a more laid book look, or with a pussy-bow blouse and pumps for something more polished.

Alexa Check Linen Jumpsuit, £125.00 Kitri kitristudio.com


Frills, bows, puffed sleeves and polka dots? Sounds a wee bit over the top, but Zimmerman has pulled it off with this playsuit.

Painted Heart Cascade ruffled silk playsuit, £585.00 ZIMMERMANN at matchesfashion.com


Sometimes you want a bag that’s a little more casual, but still adds a bit of prep and polish to your outfit. Thankfully, the basket bags that have been trending for a while now fit this request perfectly.

Wicker Handbag, £22.99 Zara zara.com


A slim scarf can be the perfect way to accessorise an outfit. Be inspired by Audrey Hepburn in Roman Holiday and tie it around your neck, or go for another glamorous Hollywood starlet, Grace Kelly, and tie it loosely beneath your chin.

Tropical printed scarf, £3.49 Mango mango.com


This Solid & Striped one piece just screams sailor – and with options in peach, navy and black, you’ll definitely find something suited to your skin tone. The contrasting trim and buttons combined with the low scoop back make for a summer staple.

The Harlow, £127.00 Solid & Striped solidandstriped.eu


Is there anything more preppy than wearing a hat that looked like it could’ve belonged to a private school boy? Fun anecdote: in Sydney, it was rumoured if you ran over a hat that was part of the uniform of a specific private boys school, it wouldn’t break. Even if you ran over it with a bus.

Klint Hat, £163.00 JANESSA LEONE at revolveclothing.com


The Breton shirt has been a chic French staple for centuries now. Modernise it a little by adding a third colour, and cropping it slightly. I’m sure Blair Waldorf won’t mind too much…

Cropped top, £3.99 H&M hm.com


I got a pair of these sunglasses in cream when I was in Amsterdam, and they’re possibly the most over-the-top thing I own. And I love them, and I’m sure preps across the world have a soft spot for them too.

Sarah Oversize Pink Heart Cat Eye Sunglasses, £8.00 boohoo boohoo.com


This suit set just screams Clueless – and if Cher Horowitz didn’t embody 90s prep, who did? The pastel of the gingham softens the entire look and makes it a bit of a more relaxed power suit.

Sita Suit Set, £228.00 Free People freepeople.com


Once again, my picks for prep veer into the twee territory. But how can you not have spring in your step when you literally have flowers adorning your feet?

Sylvie Sandals, £185.00 ANCIENT GREEK SANDALS at farfetch.com


Pleated midi skirts seem to be the seasonal gift that keeps on giving – and I for one can’t get enough of it. This one is in a bold firecracker red colour, guaranteed to turn heads. Women’s magazines go on about “day-to-night” pieces, but this is genuinely one of them.

Satin Pleated Skirt, £89.00 Whistles whistles.com


There’s no way you can have a clothing listicle about Blair Waldorf without recommending a headband. Jennifer Behr’s creations were featured numerous times as Blair Waldorf’s headwear of choice and became a trademark for the character.

Rowena Circlet, £472.00 Jennifer Behr jenniferbehr.com


Post Author: Kate Edwina

Kate Edwina
The great loves of my life (after Reese's Peanut Butter Cups and Harry Styles) are fashion, feminism, pop culture and, of course, writing. Being able to combine these is the ultimate professional dream. You can catch me obsessively repinning images of Bella Hadid, or buying as many feminist t-shirts as possible. Follow me @kateedwina

Leave a Reply