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Outfit Remix: How to Dress Preppy

December 3, 2015

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Photos by Michelle Dorman Photography

Sweater: Brooks Brother (similar) | Blouse: UNIQLO | Cords: Loft (similar) | Necklace: Banana Republic | Ring: Stella & Dot | Earrings: Anthropologie |Boots: Corso Como (similar)| Bag: Foley + Corrina (similar) | Lipstick: Wet n Wild (color Stoplight Red)

This might be my favorite shoot to date. I know I’ve said that before, but our city’s skyline is hard to beat. Although it was overcast and cold, that didn’t take away from the picturesque setting.

I feel most comfortable in a button down shirt and a pull over sweater. I love the preppy aesthetic and fail proof formula.  The last time I wore this sweater, it was during the warmer months and didn’t call for any layers. This time around, I added an oxford shirt, navy cords, and tall brown boots. I swapped out the bag, changed up the hair and added some different accessories. I’m a big fan of this necklace. It resembles a classic locket.  The bright red lips were an absolute must! I can’t believe I am just now getting hip to wearing red lippies. I feel so sophisticated and polished.  If only everything in life was that simple. This look reminds me of the 1970s tragic film Love Story. Have you seen that movie? It is known as one of the most romantic films of all time. The collegiate setting and east coast fashion is perfect.

Prep Style 101

The key to dressing preppy is buying classic and or investment pieces. Think timeless and chic. Before buying a piece, ask yourself: would I wear this in five years? If the answer is no, then put it back.

Preppy Staples

  • Pearls Be sure to pick up a pair of earrings, necklace, bracelet, or any other pearl item.
  • Jewelry I would recommend a classic monogram pendant, locket, or both.
  • Shirts The classic oxford cloth button down shirt and pussy bow blouse are timeless pieces that can be worn in a variety of ways.
  • Sweaters Great investments and fun to style. For extra prep, get a shaggy dog sweater.
  • Coats I would go for a classic peacoat, wool toggle coat, and a trench for the warmer months.
  • Skirt and dresses Purchase these in neutral colors so they can be easily intermixed with others items in your closet.
  • Pants Definitely invest in a couple pairs of tailored pants and some denim.

Where to Shop

I would definitely take advantage of second hand shops and other thrift stores for timeless pieces. Get items dry cleaned or hand wash.

If you prefer to buy new, I would check out:

  • J.Crew
  • J.Crew Factory
  • Brooks Brother
  • Joules
  • Vineyard Vines
  • TuckerNuck

Want more prep inspirations? Check out the archives.

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Related

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  3. Outfit Remix: Ruffle Pleat Cardigan
  4. 8 Closet Staples You Need Right Now

16 Comments · Labels: Fashion Tagged: Outfit Remix, Prep Style, Styling tip

Comments

  1. fashionandstylepolice says

    December 3, 2015 at 2:06 am

    I love this look, the sweater is so gorg.

    Reply
    • herrmj says

      December 4, 2015 at 11:08 am

      Thanks Stella! 😘

      Reply
  2. Amelia Vesper says

    December 3, 2015 at 1:47 pm

    So cute! You are totally channeling Ali MacGraw. And great location for your photo shoot 🙂

    Reply
    • herrmj says

      December 4, 2015 at 11:10 am

      Thanks Mil! I love that you got my reference. Great minds. 👯

      Reply
  3. Margaret says

    December 3, 2015 at 4:11 pm

    You are rocking the preppy look. I love the sweater and button down shirt.Your.hair is darling and loving the red lipstick, you look amazing. I guess I’m bias because l am your mom.Love you

    Reply
    • herrmj says

      December 4, 2015 at 11:12 am

      Thanks Mom! You know that I love preppy. Thank you for the sweet words and compliment. It’s always appreciated. 😘

      Reply
  4. My Fashion S/ash Life says

    December 3, 2015 at 11:26 pm

    I know this is an outfit post but I want the baaaag, it looks so roomy and zippy and I love that! This look is tres Preppy Cute and you seem to find nice locations for your shots! ( :

    Reply
    • herrmj says

      December 7, 2015 at 4:56 pm

      Lol! You’re so funny. You can like whatever you want. This bag was a good find. I was lucky to get on sale.

      Thanks so much! I love prep style. I feel fortunate to live in such a great neighborhood too.

      Reply
  5. Molly Clifton says

    December 4, 2015 at 4:55 pm

    Wow so many things I love about this!

    If I know anyone to pull off this preppy style, it’s YOU! You do it so well! You definitely pull off those red lips too. Beautiful color on you! I definitely need to watch that movie! I love a good flick! Also, love the location. So Pacific Northwest. Great post!

    Keep smiling!
    Molly | http://www.stylemissmolly.com

    Reply
    • herrmj says

      December 7, 2015 at 5:01 pm

      Aww, thanks Molly! You’re so sweet. Such a nice comment. I appreciate so much!

      The movie is sad, but definitely worth checking out! 😀

      Reply
  6. juliannaclairelynch says

    December 4, 2015 at 5:18 pm

    You are my preppy blogger babe and I LOVE it:) No one pulls off preppy looks the way you do and your smile is so contagious! Happy Friday:)

    xx Julianna
    http://www.blushandcamo.com

    Reply
    • herrmj says

      December 7, 2015 at 5:02 pm

      Thanks Julianna! You always leave such nice comments. Thanks so much! You’re the best. 😘

      Reply
  7. Nichole Darrelle says

    December 5, 2015 at 7:01 pm

    Great remix of the tennis sweater! It’s always so fun to see a piece styled in multiple ways! I also love your hair like this <3

    Fishbowl Fashion

    Reply
    • herrmj says

      December 7, 2015 at 5:04 pm

      Thanks Nichole! I appreciate you stopping by and commenting. What a lovely surprise. Thanks for the kind words.

      Reply
  8. deefordana says

    December 16, 2015 at 1:33 am

    This is just a cute sweater! Love it! and babe, I know I tell you this all the time but I adoreee your smile! It always makes my day!

    Wishing you a great day my love

    Reply
    • asaherrman says

      December 16, 2015 at 4:41 pm

      Aww, such a sweet comment. Thank you! You made my day. :*

      Reply

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