Ever since moving to the Mid-Atlantic in 2005, I’ve struggled with how much preppy to incorporate into my wardrobe.  I like the preppy look, but when I wear polos and Wayfarers, I feel like I’m wearing a costume.  Like, at any moment, I expect Molly Ringwald to pop out from behind a set piece and invite me to the record store to eat Pop Rocks and drink Tab.  

Regardless, preppy is one of the spring trends that people in the know (the writers of all those glossies unceremoniously crammed into my mailbox–thanks postal service) keep talking about.  So here are a few preppy pieces that I like.  Whether you wear them all at once or break them up with non-preppy attire is up to you.  Just remember that Keds grass stain easily when Patrick Dempsey comes to pick you up on his riding lawn mower.

Sunglasses: Ray Ban Wayfarer ($125) Blazer: Splendid Stripe Jacket ($198) Sweater: J.Crew Cable Knit ($70) Skirt: Carven Pleated Skirt ($140)

Shoes: Keds Classics ($35) Bag: Drake and Hen Canvas Tote ($210) Dress: Polo Ralph Lauren Logo Dress ($195)

You thought I was joking about the Keds, didn’t you?

The bag is from a company called Drake and Hen.  I adore the striped lining and the bright colors it comes in.  If you want a similar bag in a friendlier price-point , I love this canvas Guess tote at $108 and the classic Land’s End canvas tote at $50.  

Also, I discovered this bag on my new favorite blog Chevrons and Stripes.  Check it out.