OOTD: Trying On Preppy

Blogging has opened me up to so many different styles that I would normally not see in my hometown, but one style that is very…


Blogging has opened me up to so many different styles that I would normally not see in my hometown, but one style that is very prevalent here is preppy. I’m not talking preppy in the sense of impeccable tailoring and layering of stripes and plaid, but as in the mid-south’s definition of preppy: Abercrombie, American Eagle, and Aeropostle. I won’t lie. In high school, I tried to stuff my body into the clothing these stores sold since they were so popular, but they never fit me correctly and I didn’t think preppy was a look I could pull off. A couple of weeks ago I saw a preppy outfit floating around tumblr that I actually felt could work for me, so as soon as my Evans green jeans came in, I was off to try on my preppy-ish look.

My look definitely missed the crispness of the typical prep style. The folding of my jeans was haphazard, and the collar of my shirt won its war with me, but the style pushed me to layer in ways I typically do not. Letting the boldness of the jeans shine, I went with a neutral top with a button down shirt and textured sweater. I’ll admit; this outfit was pretty warm, and I definitely could only wear it when I know I’ll be in air conditioning!

After falling in love with my Olivia + Joy Miss Priss Satchel (seen here), I went on a search to see what other styles Olivia + Joy offered. I somehow trekked upon a deal where I paid $40 for $90 dollars worth of merchandise, so I hopped on that deal and got my second purse. It has the same opening as the satchel, but with different details in the synthetic snakeskin pattern and shape. I also added a stone ring to simply accessorize the outfit.

Button Down Shirt: Old Navy,  Sweater: Gap Outlet, Jeans: Evans, Shoes: Target, Ring: Forever21, Handbag: Olivia + Joy

I may not have ever reached my hometown’s idea of preppy (although at this point I wouldn’t want to), but I did figure out ways that preppy style can work for me. Want some preppy inspiration (much better than my look here!)? Check out this post from the blog Unabashedly Prep. It definitely widened my ideas about “preppy” and is making me have tweed-envy. I love that a preppy style is completely appropriate for school, work, meeting someone for drinks, or even going to a casual party. The crispness (even if I missed the mark in my look) elevates it to being dressy, but it’s still a comfortable and casual style to wear everyday.

Do you like a preppy style or aspects of it? What kind of style is popular where you live?


A reader just sent me a twitter picture of her version of the preppy look inspired by this post. Thank you E. for letting me post this! Doesn’t she look amazing 🙂 I’m loving the sweater’s color.


  1. Rebecca, I love this on you! Very academic chic, too. I can see why you love the Oliva + Joy bags, they are fabulous.

    When I was in middle school, Tommy Hilfiger was “in” and I tried to wear their clothes. Ah, the young and stupid. The area I grew up in varied in style – preppy, skater… but it is all the same brands that were cool when I was that age.

    1. Thanks Nicole! Yea there were definitely different styles (I dabbled in “skater” wear), but the preppy style was hailed as the popular style. I’m sure most people endure that kind of desire to fit in during their teens.

  2. I really like this look! It actually suits you really well and I love the color of those green jeans!

  3. I really love this color combination and that you paired it with black shoes/bag instead of brown. Great idea on the ring, too.

    What style is in where I live? Camouflage. The wear-everywhere-like-you-just-stepped-out-of-your-hunting-stand stuff. It’s gross, imo! 🙂

    1. Thanks Greta! Camo is a big thing here too! I have to admit that it’s not my favorite look, but neither is trekking around in the woods to kill live game! haha 🙂

  4. You look great! This sure supports my belief that a hand bag and a ring make a nice outfit look perfect : ). I really love the stone ring ♥ (they’re at the top of my christmas wish list ^^).

  5. If you happen to hear someone screeching incoherently and waving their arms in the air as they charge at you, don’t worry. It’s just me… coming to steal this whole outfit… because it’s mine. MINE, I TELL YOU! =P

    p.s. That bag and I are destined to be together, I think.

  6. You look amazing Rebecca, and I love your Evans jeans, they work perfectly for the prep look. I’ve never tried the preppy style, but I think I will after seeing your fab outfit. 🙂

  7. Can we discuss how much I love this look… So super cute! and I like the way you styled you pants, and that handbag is a must!

  8. hello darling!! just came across your lovely blog through IFB network! I am looking to get to know other Charlotte bloggers since I am fairly new to charlotte. I love your blog, you have such great style! hope you have a good holiday! keep in touch love!

    1. Hi Pam! Welcome to Charlotte! I don’t know any other Charlotte bloggers, so I’d love to connect with you and others and talk about blogging life :). I’ll head over to your blog soon!

  9. I love this outfit and have yet to see it on you! I’m trying to find new ways to wear the clothes I already have instead of the same old boring things every week that I wear to work. This has definitely let me see some of the things I had in my closet in another way. Oh…and I might have to borrow that! 🙂

  10. I love that you love yourself for the beautiful woman you are and that you are not shying away from trends because of your size #gosister

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