Classic Preppy Style in New England

summers in new england

It’s Friyay! This week was just long and tiring for me. I had so much to do at work and not nearly enough time to do it all. I keep saying every week that the weekend will be strictly for relaxing and every weekend I don’t relax at all. In the past, my family and I have taken vacations during September and October because the weather is so pleasant. Last year, we went to New England for a week-long getaway. Can I just say how excited I was to wear preppy fall clothes in the region where “preppy” was born? Read on for a look at my outfit!

jcrew lobster sweater

If you’re a J. Crew lover like me, you’ll know that this is their super popular lobster sweater. I always get compliments on it! Unfortunately, they don’t sell it anymore but every once in awhile you can find one on eBay. When I was shooting these photos with my sister, the wind kept whipping my hair around and making it hard to get a good photo. But the sun was perfect and the water was so blue!

salem during halloween

I’m also wearing my favorite Abercrombie lace shorts that you’ll probably see on my blog a million times until I’ve worn them out. One of my favorite things from my vacation in New England was seeing how well my personal style fit in with my surroundings. Even my cat eye sunglasses were reminiscent of Jackie Kennedy ‘summering’ on the Cape! During the summer, I focus my wardrobe on nautical stripes and classic shoes like Jack Rogers and Sperry. During the awkward transition months like September and the early part of October, I combine those styles with denim, fuzzy scarves, and riding boots. It was so much fun literally feeling like I was blending in with the scenery. I just can’t seem to do that here in Dallas!

how to dress for fall

Preppy fall style

Spending a few days in the birthplace of preppy was so nice! Spending time with my family was even better. Now that I live so far away from them (they’re all back on the east coast), I realize how important these trips have been in my life. In the long run, what I wore doesn’t matter much either. But I certainly adore this outfit! Below are a few links to similar items!Β Β 

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I'm a Dallas fashion and mental health blogger! I love sharing affordable styles anyone can wear and also sharing mental health topics so people don't feel so alone.

17 thoughts on “Classic Preppy Style in New England”

  1. I had that sweater! I wore it to pieces and finally had to retire it. I lived on Martha’s Vineyard for several years, so I have an affinity for lobster. πŸ™‚ It looks great on you!


  2. I love New England! Yankees often get a bad rap for being unfriendly. I found them to be friendly and funny! Love the preppy look and always have. Back in my high school years, preppy was very in. I wore tretorn tennis shoes, Izod shirts, sperrys, pappagallo shoes and purses. It was such a classic look that never goes out of style. Love your pictures and your outfit!


    1. Thanks so much! Yankees are some of the funniest people I know. I actually have a pair of my mom’s old duck boots that are so preppy and still in style!


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