7 Street Style Ways to Look Preppy This Summer ...

Vanessa Jul 26, 2014

There are so many fun and easy ways to look preppy this summer. Whenever I want to go for a preppy look, I always think, WWTSW? What would Taylor Swift Wear? It's a great system because she's the perfect example of always looking preppy chic. You'd be surprised at just how many different ways you do it! Check out some of the cool street style ways to look preppy.

1. Collared Shirts

Collared Shirts The easiest way to nail the "preppy" look is to rock a collared shirt. I love when it's paired underneath a crewneck sweater! However, it might be a little too hot this summer to do that. So, pair your collared shirt under a tee instead. I love the idea of wearing it underneath a graphic tee! It would definitely be a 'preppy meets rocker' type of look. This is just one of many ways to look preppy this summer.

2. Tailored

Tailored Tailored items are perfect for preppy outfits. Form-fitting blazers, tops, shorts, etc. are a great addition to your outfit. It keeps you looking "put-together" without having to try too hard.

Frequently asked questions

Thanks for sharing your thoughts!

Please subscribe for your personalized newsletter:

3. Classic Look

Classic Look Preppy outfits are all about looking sleek and sophisticated. Nothing screams that out more than a classic black and white outfit. Even though colors are always a great idea, black and white is timeless. You can pair some black skinny jeans with some white converse. For the top half of the outfit, you can go for a layered look or a white button-up. I think black and white always looks good together and it keeps you looking fabulous.

4. Uniform-inspired

Uniform-inspired If you have a school uniform, think 'Gossip Girl'. Blair had the ultimate preppy school-girl style! If you're no longer in school but wish you had the chance to rock the cute uniforms, create a similar outfit. Knee-high socks are a must. Pair it with a high-waisted skirt and button-up top. To complete the school-girl vibe, add a cute bow-tie! You can add some color to the outfit with a cardigan or cross body bag.

5. Summer Dress

Summer Dress There are so many easy ways to 'prep up' your summer dress. I love color block dresses (you can find some on jcpenney.com)! Adding a thin belt at your waist completes the whole look. Of course, you can't forget your summer wedges and big floppy hat.

Gallery Spotlight

Save and share the images that inspire you. Tag @allwomenstalk to get featured.

6. Blazers

Blazers Blazers are a great addition to any preppy outfit. I think it ties the outfit together, making it look tailored. It's definitely something Taylor Swift (the queen of preppy ensembles) would wear. You can go for solid colors or printed blazers. Personally, I love floral-printed ones! You can never go wrong with that.

***

Blazers really offer that transition from casual to chic in no time. Imagine them paired with crisp chino shorts and a simple blouse - perfection! And don't be afraid to play with color; summer is all about vibrant hues. A bold yellow or baby blue can add a playful twist to your look and still keep it classy. Accessorize with a statement necklace and boat shoes for that effortless Ivy League vibe. It's a smart-casual balance that's just right for a brunch date or an office that leans into summer style!

7. Mix/match Patterns

Mix/match Patterns This summer, don't be afraid to mix and match different styles and patterns. As long as the items coordinate, you can create some pretty amazing outfits. Try pairing a button-up chambray top with a polka-dot skirt, or a lace sweater with a pencil skirt. Throw on a blazer and you're good to go!

Well, there you have it. These are just seven out of many awesome street style ways to look preppy this summer. If you feel like channeling your inner Taylor Swift, these are the outfits for you. Of the list, which look is your favorite? Which will you be trying to recreate?

Feedback Junction

Where Thoughts and Opinions Converge

Gorgeous

Good article but i felt all the picture reference, except summer dress, were winter/autumn oriented.

EST 2005

Evolve. Empower. Elevate.

Creators on the platform
3,000+
Total social reach
12M+
Features published
100K+
New Earn badges & level up while you read

Create your profile. Earn badges. Level up your reading.

Join Allwomenstalk to track your streaks, collect badges, and earn XP for the things you already do—reading, sharing, and taking quizzes.

  • 🔥
    Daily streaks with gentle boosts for 3, 7, and 30 days.
  • 🏅
    Collect badges like Reader I–III, Socialite, and Quiz Ace.
  • ⚡️
    Earn XP for reads, deep reads, likes, comments, and shares.

It’s free. Takes 30 seconds. Already have an account? Sign in.

10,000+ badges earned last month

Level

3

Streak

7 🔥

XP420 / 700

Badges

🔥 On a Roll
📖 Reader I
📣 Socialite

Trending products

Other Cool Reads

Related Topics

street style casual summer outfits adorable dresses styleways dress articles of clothing famous burger teriyaki sandwich photos outfit sporty casual concert outfit loreal paris color riche stylo skirt types of animal print diy fashion projects