It’s a Smile, It’s a Kiss, It’s a Sip of Wine, It’s..

Summertime! It’s kind of sad to think that we have one more real weekend of summertime left, but I’m also excited for fall. I am trying to be outside as much as I possibly can these next few weeks. The weather is so gorgeous, but a constant reminder that it’s almost over. It’s bittersweet.

I wore this outfit out with a few friends last Thursday night. The bar we went to plays country music on Thursday nights and has a great outdoor patio. We were able to enjoy the wonderful weather and some good music!

I kept it casual with jean shorts, a button-down top, and Sperrys. It has been getting a little chilly at night so I wanted to wear jeans, but figured I should take advantage of the time I’m able to wear shorts without tights.

Top: Polo Ralph Lauren (similar)
Shorts: Joe’s Jeans
Shoes: Sperry Top-Sider
Watch: Michael Kors

I’d love to hear from you! The weather can get a little chilly, but you want to take advantage of summer at the same time. How do you transition your style from summer to fall?

(Photog: Herrmann)

Leave a Comment


  1. 8.29.11
    Anne Culbert commented:

    You are very timely, Jessica! Today show just had a feature on the same topic. Still am not brave enough for white/off-white pants after Labor Day. Maybe this will be the year to take a risk? BTW, did you know that your mother used to keep track of what she wore in highschool? Being style concious is in your genes…
    PS. Happy Birthday week!!!

    • 9.14.11
      Jessica commented:

      I didn’t know that! I’ll have to ask her about it. And you can DEFINITELY wear white pants after Labor Day 🙂

  2. 8.29.11

    I love the look of a white button-down shirt. Casual yet chic. I wish the weather was starting to cool off here in Florida. I still have a few more months to go! But when the weather does start to cool off, I’ll usuall try to add a cute denim jacket or just wear my tanks with jeans instead of shorts.

    • 9.14.11
      Jessica commented:

      Denim jackets are a great way to transition!

  3. 8.29.11
    Chelsea commented:

    Layers! Cardigans, scarves, layers are how I make it into fall. Unfortunately, it is over 100 degrees here, so I don’t even need to start thinking about that yet. xoxo

    • 9.14.11
      Jessica commented:

      Layers are perfect for transitioning to fall! Scarves are my favorite!

  4. 8.29.11
    Defining Tabitha commented:

    New to your blog, but I’m from Chicago too. 🙂 I have those same Sperrys and they’re great go tos for the summer.

    • 9.14.11
      Jessica commented:

      I love meeting other Chicago bloggers! We’ll be in touch!

  5. 8.29.11

    layers, especially cardigans! Where I’m from fall means cool in the mornings and at night but super hot during the daytime! So layer that are easy to put on and take off are ideal

    • 9.14.11
      Jessica commented:

      Different temperatures throughout the day make it a little more difficult, but cardigans are great for that!

  6. 8.31.11
    Mandy commented:

    I almost wore this exact outfit a few weeks ago! You look great. I use light layers and 3/4 length sleeved tops for my transition.

  7. 10.25.19
    Tara Drott commented:

    Really late I know but great outfit all the same, love how simple yet preppy it is, really like how you included the gold Sperrys! In fall though for me nothing beats layering with denim and chambray!