The Best Preppy Style – the Milly Breton Striped Dress

New York Street Art

Breton Striped DressNude Patent Carrson Sandals {also worn here} Straw Boater Hat | Aviator Sunglasses |  Red ClutchLawson Cuff | Elisa Pendant Necklace

Hi, friends! Today, I’m sharing one of my favorite preppy outfit ideas – this Milly Breton Striped Dress. Furthermore, we photographed this style in front of my go-to murals in Dumbo Brooklyn.

Beyond the high/low hemline of the dress, I love the pale blue striped fabric. The dress is fully lined, and the fabric lets if flow (and twirl) in the best possible way.

Nordstrom Anniversary Sale

Milly Breton Striped Dress

In order to style the Milly Breton Striped Dress, I paired it with a chic straw hat, these comfy Steve Madden shoes, and colorful pink clutch. All in all, this look just feels like the epitome of summer style, you know?

For more than a decade, I’ve loved incorporating Milly pieces into my wardrobe. Season after season, their design team brings bright, beautiful, and colorful styles to the table.

Ray-Ban Aviator Sunglasses Nordstrom

My Journey with Milly

In case you didn’t know, Milly’s owner and designer, Michelle Smith, continues to push the boundaries of what’s possible with style. I’ve absolutely loved wearing the brand at rStheCon, this insanely beautiful paint brush midi, red white and blue frocks, and beyond.

To be frank, I’ve had “highs” and “lows” with the brand. In the early 2000s, the brand underwent a complete rebranding, including a new logo and design direction. In fact, I remember touring their booth at the Javits Center at a trade show, and I was immediately shocked at the rebranding.

Nordstrom Anniversary Sale Dress

At first, I was really excited about the evolution. However, the brand started to be less classic, more cool girl. Milly’s striped, colorful brand turned towards a downtown, edgy vibe. Hemlines shortened, necklines plummeted, silhouettes became body con. Even their Fashion Week front row looked different.

Steve Madden Carrson Sandals

Listen, fashion means that brands need to evolve. However, in my humble opinion, Milly lost its way for a few years. Thankfully, they have been getting back on track, and I hold on hope that they will return to the roots of what made Milly special.

Milly Striped Dress
Nordstrom Straw Boater Hat

Styling the Look

Of all of my sunglasses, these classic aviators are probably my most-worn. Funny enough, they belong to my husband, and he’s had them since we were dating. Years ago, I borrowed them from him and realized how much I liked them, so I keep borrowing them! I love the way the aviators look with this dress.

Steve Madden Carrson Sandals

Don’t worry, he has another pair that he uses all the time. Seeing that today is National Sunglasses Day, I’m thinking of getting another pair of classic sunnies for summer, and I’m heading to Nordstrom to complete my collection – their selection is simply the best! See what’s on my wish list in the scroll below!

Brooklyn Street Art

This mural was created by MOMO. See my previous blog post from this wall here

Leave a comment

View All 16 Comments

  1. L
    Leyla wrote:

    Love that wall and your energy in these photos!! And you can’t have too many aviators…those look perfect on you!

    Published 6.27.16 · Leave a Reply
    • J
      Jenn Lake wrote:

      Aw, thanks lady! Hope your Monday is off to a great start!

      Published 6.27.16 · Leave a Reply
  2. N
    Nina wrote:

    Such gorgeous movement in that dress! You look adorable!

    xo, Nina
    Law of Fashion Blog

    Published 6.27.16 · Leave a Reply
  3. M
    Meghan wrote:

    Gorgeous striped dress Jenn! It looks so fun to twirl in!

    Meghan |

    Published 6.27.16 · Leave a Reply
    • J
      Jenn Lake wrote:

      Thanks Meghan! It definitely was – I may have gotten a bit dizzy though – lol!

      Published 6.27.16 · Leave a Reply
  4. B

    Gorgeous dress!! You look so stunning Jenn!

    Published 6.27.16 · Leave a Reply
  5. N

    That is one heck of a wall and a twirl you’ve got here Jenn! Nordstrom is the best place to find a complete look. I always go there first when in a pinch and now you’ve got me wanting to go there now!

    Published 6.27.16 · Leave a Reply
    • J
      Jenn Lake wrote:

      Aw, thanks lady! You’re such a natural at putting amazing looks together!

      Published 6.27.16 · Leave a Reply
  6. C
    Carrie Colbert wrote:

    I really love these photos! Well done, Jenn.


    Published 6.27.16 · Leave a Reply
    • J
      Jenn Lake wrote:

      Thanks Carrie! We had just enough time to return to Brooklyn for the afternoon when we were in NYC – I’m so happy we did!

      Published 6.27.16 · Leave a Reply
  7. S
    SarahLagen wrote:

    I love this dress, it moves so great!! Such a fun summer look and that wall is amazing!!

    xo, Sarah

    Published 6.27.16 · Leave a Reply
  8. S

    You seriously find the best walls and wear the prettiest dresses 🙂

    Published 7.1.16 · Leave a Reply


Sign up to receive Jenn's weekly newsletter, filled with exclusive content, sale alerts, and more behind the scenes charades!