My Modern Preppy Style

For my entire life – no, I’m not exaggerating – my style has been classic and preppy. With today’s fashion, my style is less shorts with animals stitched on them and more simple but classic shift dresses with a monogram necklace. But while I may not be breaking out an argyle sweater vest any time soon, I do like a good colorful dress with a pair of pearl earrings. Today’s post contains several outfits that are perfect for pearl earrings, plus where you can get some of your own and a chance for you to win a pair.

Disclaimer: This post contains affiliate links, which means that if you click them (and in some cases buy something), I’ll earn a small commission. I also received a pair of earrings from Pearl & Clasp in exchange for writing about them in a blog post, and I received another pair and am giving them away with their approval. All opinions are my own, and I did not receive any other compensation from them for this post. For more information and to learn more, check out my disclosure policy.

My Modern Preppy Style

These are all outfits that would great with pearls, especially pearl earrings! I’ve provided 2 types of outfits: office and casual. In some cases, when the brand from the product in the image is too expensive for the average person, I’ve tried to find a similar but cheaper version. These are outfits that are perfect for August and September – and maybe later in the year depending on where you live. Oh, and scroll to the bottom to enter to win a pair of earrings!


Modern Preppy Fall Style

Miss Selfridge SweaterVince Camuto Dress (Similar but Cheaper) | Maison Margiela Trousers (Similar but Cheaper) | J. Crew Embroidered Top


Modern Preppy Fall Fashion

J. Crew Shorts | J. Crew Top | 7 for All Mankind Jeans (Similar but Cheaper) | Madewell Top

Earrings from Pearl & Clasp

Pearl Earrings

Pearl & Clasp sent me a pair of earrings and oh how I love them. If you knew me in high school and college, there’s a very large chance that you regularly saw me wearing pearl earrings. I’ve always loved them, and as I said, my style has always been classic on the side of preppy. The pair Pearl & Clasp sent me are the perfect size for daily use. They’re not so small that they can hardly be seen and they’re not so large that they hurt my ears. Plus, the quality is great. I’ve been very happy with them so far, and I don’t see that changing! These are 9 mm and come in 3 colors, and they’re just $34.

Enter to win your own pair of pearl earrings!

This giveaway runs from 8/12/2016 12:00 AM EST – 8/18/2016 11:59 PM EST. It is only open to US residents who are at least 18 years. Within 48 hours of the giveaway, a winner will be chosen and their entries verified. Once they are emailed, they have 48 hours to respond to claim their prize, and after that time, I will choose another winner. The prize will be mailed via USPS ASAP after the winner responds. If you have any questions, please email

a Rafflecopter giveaway

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    […] My Modern Preppy Style, Spring to Summer Fashion, 5 Tips for Summer Decoration, 20 Great Summer Recipes […]

    July 10, 2017 at 7:12 am
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