How to Pull Off the Prep-School Look





I know what you’re all thinking… First it was graphic tees, and now we’re talking about prep school?!

Hahaha despite not being in school anymore (although I’ve been having thoughts of going back), there’s always something about September that makes me think of prep school and uniforms! And in particular, I can’t help but think about one of this past decade’s most iconic shows – Gossip Girl! There’s just something about the fashion on that show that still feels so classic and timeless that it seems to live until this day, don’t you agree?

So despite being in my twenties already, once September rolls around, I can’t help recreating these Gossip Girl, prep school inspired outfits because the inner fangirl in me just simply can’t resist! If you’re interested in these types of outfits too, read on to see how I pull off this prep school look that’s not only inspired by some of Blair and Serena’s most iconic styles, but that also looks mature and sophisticated enough for the corporate environment that I’m working in!

1. Never Underestimate a White Button Down



A white button down is iconic as it can get when it comes to choices for a top. There are so many different variations of the classic white button down, but I wanted to mix in equal parts “Serena” and “Blair,” and I did this by picking out a collarless button down with bow-tie details at the wrists and ruffled sleeves. The collarless silhouette is a little more effortless than a traditional collared shirt, but at the same time, the feminine details, like the little bow at the wrists and the ruffled sleeves, make this crisp shirt stand out amongst a sea of other white button downs, making it the perfect piece in a “non-conforming” uniform that speaks volumes about your personal style.

2. Choose Different Colored Plaid Skirts



Plaid skirts are a definite wardrobe staple when it comes to prep school uniforms. Rather than converting to a typical green, blue, or gray blend, though, I opted for a beige and white pattern instead. Not only does this lighter palette stand out prettily, it’s also perfect for the early fall, since I typically like to wear darker colors as the months get colder.

Also, another tip – play attention to silhouettes. For a more “conventional” prep school look, a slightly flared or a-line skirt is perfect for that pure school-girl image, but since I also want my ensemble to work for the office, I chose a form-fitting pencil skirt, giving it a slightly more mature, yet sensually feminine look.

3. Don’t Forget the Blazer



Although it may still be a little warm for blazers, depending on where you’re living, I don’t think any prep school outfit will be complete with this structured classic.

When it comes to timeless outerwear, such as blazers, I like to stick with iconic colors, like black or navy, because they go with just about everything. Plus, these sleek color choices also elevate the whole ensemble, pulling the look together for a sophisticated outfit that’s resonates the regal, understated sophisticated of an Upper East Side prep school uniform.

4. Opt for Nontraditional Shoes


While uniforms are usually worn with knee-high socks and Mary Jane oxfords, or tights and Tory Burch flats, there’s something fun and exciting about adding a fun little “dress code violation” to your outfit, don’t you think? Besides, it’s exactly what an Upper East Side student would do, right? 😉

For this particular ensemble, I couldn’t help but reach for my suede ankle boots, since they go perfectly with the color palette of my skirt. Plus, no one can ever complain about a little added height, don’t you agree?



On Me

Express Ruffle Sleeves Button Down Shirt in White

bibyseob (from Suggesty) Button Down Mini Skirt in Beige

Forever 21 Men Blazer in Black

Urban Outfitters Suede Ankle Boots in Camel

Ted Baker London Kittii Cat Animal Leather Crossbody Bag in Rose Gold

  • Barkley Dog Version here


Are you a fan of this preppy style? And do you miss Gossip Girl as much as I do? Let me know in the comments because I always love hearing from all of you!

**I received this skirt complimentary from Suggesty. All opinions are my own.

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