I cannot believe we are reaching the end of the summer. I mean, in my mind, it just started. It’s also a little bittersweet for me because fall happens to be my favorite season. I love summer weather — I just don’t like the frizzy hair that comes along with it. But just because my hair doesn’t do well in these hot temperatures, doesn’t mean I don’t plan to milk the last few weeks.

With back to school quickly approaching, I am sharing my top five end of summer essentials that are perfect for transitioning into the first few weeks of September. If the weather in Chicago is anything like where you live, we are afforded a few weeks of decent temperatures, so transition pieces are key.

1. Romper

Rompers are perfect for summer, but they also transition well in between seasons — I love them — except for when it’s time to go to the restroom. Can you relate? They are so convenient until you have to use the potty. Please forgive me! Even though my sons are four and six, I still use the vocabulary of a two year old.

Okay, now seriously, outside of the restroom, rompers are the perfect item to transition from day to night (and summer to fall). This chambray romper I’m wearing from ASOS has sleeves, which is ideal for the not so warm days, or, the chilly nights you often have if you live on the West Coast.

The off-the-shoulder moment is just the cutest — I’ve really loved this trend. For me, the length is everything, too. I’m 5’11 — needless to say, sometimes it’s difficult to find rompers that are long enough for me. This is just the right length, but I’ll still release the hem to wear with heels. Another bonus — it’s so comfortable. The light chambray fabric makes it so light and breathable for summer, but all the coverage also makes it ideal for fall.

2. Bag

As a mom of two young boys, I always have a big bag. I try to carry small bags during the day, but it’s just a pain. I’m still wondering at what age will my bags become smaller? Please feel free to weigh in below in the comments.

Anyway, I got this super cute canvas bag at the Nike Air Society event in Chicago. I got to personalize my Nike Air Society canvas bag with patches from Vichcraft, which is the local independent studio of Jenna Blazevich — a Chicago designer. The patches that I got to choose from for the event were all women empowerment driven, which I love. I chose black and gold metallic ones to compliment my bag — one a Fempire patch and the other a sacred heart. I take this bag everywhere because it definitely meets the requirements for a “mom bag”.  It’s also a great beach tote and thanks to Chicago’s awful bag tax, a great shopping bag as well.

3. Hat

I have several bad hair days during the summer time.  Actually, scratch that, the weather doesn’t have anything to do with it. I’m always running five minutes late and during the summer it’s closer to about ten minutes.  A great straw hat can make any outfit go from boring to chic and keep your hair in tact. This J.Crew stunner does the trick. It comes in white and natural with a black grosgrain ribbon. Simple and stylish.

4. Earrings

We all know tassel earrings were all the rage over the summer. Actually, I think bold statement earrings replaced the statement necklace this year. Don’t let the winding down of summer stop you from rocking a bold pair of earrings, though. I got mine from Baublebar and I love them. Yellow always puts a smile on my face and these earrings are no exception. I also have several pairs of earrings that I got at J.Crew over the summer that are showstoppers as well. I’ve linked some of my faves.

5. Shoes

Summer shoes can transition into fall as well. The slide, mule, and a chic sneaker can lend a cool factor to any stylish outfit during the early weeks of the cooler season. Many people view flip flops as a summer shoe, however, flip flops have been a fave of mine since my high school years and I’ve always carried them over into fall. They are so comfortable and quick and easy for a running-late-mama like me.

I discovered the brand Ipanema several years ago while visiting Rio de Janeiro. In my opinion, they are far more comfortable than the other Brazilian brand. The coolest thing about Ipanema is they also design flip flops that actually look like sandals and not just thong flip flops. Fashion and function is always a great formula for me.

With just a few weeks left before back to school, I want to enjoy the last of my summer style. I also want to take advantage of all the end-of-summer sales and get good wear out of everything. If Chicago weather fails me and chooses to get colder sooner than I prefer, I am all for transitional pieces that offer me a little more longevity into the cool temps.

Romper: ASOS Hat: J.Crew Bag: Nike Air Society Shoes: Ipanema Earrings: Baublebar 

Photography: Hallie Duesenberg