Have you ever moved to a new city or town and felt completely out of place? Well, when I moved to New England, I was immediately intimidated by the ‘New England Prep’ style.
I’m from an area where fashion is progressive and dressing edgy is cool. So, I felt very uncomfortable amongst the bright-pink, preppy Lily Pulitzer dresses and jeans without rips.
My insecurities about the way I dressed grew worse upon meeting my boyfriend’s family. They were no short of a Vineyard Vine’s Ad- the only thing they were missing was a golden retriever. As a result, I found myself wanting to cover up the rips in my jeans and put a sweater on to conceal the slightest bit of cleavage.
Although it was unfamiliar, I did admire the ‘New England Prep’ style. I then decided I wanted to incorporate it into my own wardrobe, but in a way that didn’t cause me to lose myself.
Somehow, I managed to incorporate it into my trendy wardrobe without allowing seersucker to become a soul-sucker. Now, scroll through to see how you can do the same!
Gingham Plays for Both Teams
Gingham is most famously preppy- but when styled a certain way it can be edgy too. Check out these gingham dresses from Nastygal and Misguided that are a perfect mix of the two classic styles.
$50
$31
Stripes Define ‘New England Prep’ Style
Traditional stripes have evolved from where they once were. Add these striped pieces to your wardrobe for some preppy-enough vibes.
$88
$40
Loosen up your Button-Up
Your collard shirt doesn’t need to be crisp and tight. You can wear an airy, comfortable blouse and still look preppy. This is the perfect look for your weekend on the Cape!

Image Courtesy of www.revolve.com

Image Courtesy of www.revolve.com
$167
Embroidered Beauties
Perhaps embroidered anchors are a little too over the top for you. Check out this embroidered beauty you can wear instead. If this classic white and blue top doesn’t say ‘night out on the Vineyard’, I don’t know what will!
$43
Toned Down Lily Pulitzer
Intimidated by all the Lily? Here’s what to wear when you’re not ready to take on Lily Pultzier:

Image Courtesy of www.nastygal.com
$47
Sweaters that Sneak the Preppy in
Not ready to commit to a Vineyard Vines pullover? Check out these cool sweaters that have a touch of nautical to them.

Image Courtesy of www.shopmixology.com
$95
$72
No Frills Pink
Not into having a giant pink whale plastered across your chest? Here’s our secret to wearing pink without looking like a Barbie doll: play with different shapes and textures.
$50
$31
Make Denim look Cool without Rips
Yes, there are more ways to make denim look cool (or cooler, I should say) without distressing them. The best part about them is that they are so versatile that they will go with practically everything in your closet.
$189.95

Image Courtesy of www.shopbop.com
See, going preppy isn’t so bad! These stylish pieces are the perfect mix of trendy and nautical, and are sure make your transition to ‘New England Prep’ style a (sea)breeze!
Looking for more summer fashion pieces? Check out these hot one-piece swimsuits for under $40!