If you’ve ever watched the TV series “Gossip Girl”, then you’re familiar with the two main characters – Blair Waldorf and Serena van der Woodsen. While Serena always exuded a boho-chic downtown vibe, Blair was best known for her preppy uptown looks.

Since one of the cutest Fall fashion trends to wear this season is the preppy plaid trend, discover my take on a Gossip Girl-inspired way to wear this fashion trend.

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

A Brief History of Plaid

For hundreds of years, plaid has been a traditional pattern to wear for Fall. Hailing from history-rich places like Scotland (where tartan plaid is a heritage style), this timeless print made the leap from Europe to the USA back in the 19th century. Since then, plaid has become a popular American style – especially for Fall and Winter.

Whenever Autumn rolls around, I often look to fashion brands like Ralph Lauren, Tory Burch, and Burberry to find this classic print.

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

As I was organizing my Fall accessories, I pulled out a Burberry vintage check handbag that I’ve had for years in my closet. This signature plaid print has always been an iconic preppy style and is especially popular in places like the Upper East Side of New York and in Carmel, California.

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

Mix-and-Match Plaids

Instead of just wearing a plaid handbag, I went for a pattern play by mixing-and-matching plaids. The key to tastefully mixing plaids (without going over-board) is to choose patterns with similar colors. While each of these plaid prints is slightly different, when combined together – they look cohesive and intentional.

  • This current plaid mini skirt by Express (which is under $50) created the perfect foundation, as it exuded a school girl prep vibe. Plus, the a-line silhouette of the short skirt made the look even sweeter.
  • Adding onto the plaid theme, I threw on an oversized plaid scarf by ASOS (which is currently sold out, but here’s a similar style) that turned up the coziness of the outfit.

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

Add a Luxe Fabric

When mixing high and low-priced pieces, an easy way to elevate your style is by combining a luxurious designer find (like this timeless velvet blazer by Theory) with budget-friendly staples (like this Michael Stars turtleneck).

A luxe fabric that is sumptuous to touch instantly elevates the look and feel of any outfit. Even for casual outings, like brunch and shopping, a velvet blazer adds a sophisticated, elegant touch. I think Blair would definitely approve!

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

The Midas Touch

Gold jewelry (like a gold tassel necklace and a chain-link bracelet) exude femininity, glamour, and class. Plus these pieces give off that uptown, preppy vibe. Another way to add a classic style to this type of look is with vintage designer jewelry, such as this pair of pearl-and-pavé Christian Dior earrings.

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

Step Up Your Game

One of the most memorable personality traits of Blair’s character on Gossip Girl was her emblazoned sense of self-confidence. Whether it was the way she carried herself or just the fact that she acted like a boss, one thing’s for certain – she always stepped up her game with her shoes.

To complete this outfit, I paired grey suede knee-high boots by Sam Edelman with simple black tights. Not only does this keep you warm when temps drop, but it also exudes a sexy, sophisticated vibe.

For more fashion trends and style inspiration, check out the Fashion & Style section on Inspirations & Celebrations.

Fall Fashion Trend: The Gossip Girl's Guide to Wearing Preppy Plaids for Fall

Shop The Guide:

 


Featured Outfit: Turtleneck: Michael Stars; Bag: Burberry; Scarf: ASOS; Shoes: Sam Edelman; Earrings: Vintage Christian Dior;  Bracelet: Julie Vos; Necklace: J.Crew; Blazer: Theory; Skirt: Express; Sunglasses: Versace (Affiliate links included)

Photography: Rachel Krueger

Styling, Modeling, and Photo Editing: Christina-Lauren Pollack

Shoot Location: Nestled on a dramatic cliffside in Carmel Highlands lies a majestic $52 million dollar compound (named “Seven Coves”) surrounded by over 4 acres of towering trees and meandering gardens. With sweeping views of the rugged California coastline, this secluded estate is situated on the legendary Spindrift Road. The unique property boasts five incredible homes, including four storybook cottages and a spacious main house (that comes complete with a grand library and a pool).

The bespoke compound has even made its way into the spotlight, as it was featured in the movie “Basic Instinct” (with Michael Douglas and Sharon Stone), and most recently was seen on HBO’s hit TV series “Big Little Lies” (in a scene with Reese Witherspoon). The property has been seen in Architectural Digest, House Beautiful, Forbes, and other publications and is currently listed by Tim Allen Properties (of Coldwell Banker Residential Brokerage).


 

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