What to Wear to a Fall Fair or Festival

August 31, 2017

Fall is really starting to heat up (although I wish it would cool down). It’s one of my favorites times of the year. In the south, it’s the start of fair and festival season. Local fairs, state fairs,  music festivals, and more. I happen to LOVE visiting local fairs and festivals with friends. Just this weekend, we went to the Red Brick Roads Music Festival in our little town. It was a blast and we got to hear some really great bands! But what do you wear to a festival like this when the weather still isn’t cool enough to rock traditional fall garb, but you’re not the kind of gal to bear it all? I’ve got some tips to help you out!

Photos by Kylie Stinson


If you’re like me, then you’re over riding the rickety, dirty, there’s a 47% chance that you’ll die fair rides (most of the time) and have graduated to sitting on the sidelines. Now don’t get me wrong. The sidelines are a blast. Overpriced, over fried fair food and lots of fun times with friends. Not to mention most of the fairs and fests that I enjoy going to have concerts some of the nights. I’m not much of a concert girl, but as long as I can lounge in the back, listen to the music, and still hear myself think (enough to chat with girlfriends and people watch) then I’m totally in!

Most of the time, I’m there for the food… Lets be real!

I always like to be fashionable when I head to fairs and festivals. I’ll probably never go to Cochella or some other large fashion forward festival, so this is my opportunity to wear a cute hat and bring out the boho (preppy boho… I’m no hippy).

A comfy tee is the perfect top. Breezy and easy to match. This tee is my absolute favorite. I bought it several weeks ago at the NSale but it’s still in stock for less than $30. It comes in 4 colors and is a total must have.

I love a soft colored skirt more than I probably should. Which is why I grabbed this blush pink one as soon as I saw it! It’s such an easy piece to wear. Paired with my favorite new espadrille sneakers and the perfect boater hat, and it’s a perfect look. I also love to carry a little backpack instead of a purse if I can as well! Hands free is always great at places like that!


Shop My Outfit


  • Reply Dealman September 1, 2017 at 7:57 am

    SO many inspiring women & I loved learning more about them – great post!

  • Reply Nellwyn September 5, 2017 at 2:28 pm

    This is such a cute outfit! Where I come from in the country a fall festival means hay rides, apple picking, and corn mazes so I usually wear jeans and a flannel that I don’t mind getting dirty

  • Reply Cecilia September 6, 2017 at 7:56 am

    I love how casual but yeah girly and fun the outfit looks. I love how you paired the skirt with the sneakers. Thank you for sharing!

  • Reply Ellie September 6, 2017 at 8:59 am

    This look is me to a tee!! I love soft pink flowy skirts and boater hats! I love the soft, simple white t-shirt you’ve paired it with. Such a cute look for a festival or fair outdoors.

    • Reply Kassy S. Randazzo September 7, 2017 at 9:39 am

      Thanks girl! It’s just so cute and comfy!

  • Reply Nadalie September 6, 2017 at 9:52 am

    How lovely! I’m all about the accessories, so I’m loving your sunglasses and hat. And the Kate Spade of course! I’m so sad skirt weather is almost over.

    • Reply Kassy S. Randazzo September 7, 2017 at 9:39 am

      Not here! The south is ALWAYS up for flowy skirts! Guess you better wear a bunch before the weather cools down!

  • Reply Vicky September 6, 2017 at 11:23 am

    I totally go to the fairs for the food. My kids go for the questionable rides run by possibly under trained employees, but give me some good old fashioned fair food. I love that you can enjoy a festival while looking super stylish!

    • Reply Kassy S. Randazzo September 7, 2017 at 9:38 am

      I remember the days when the creaky old fair rides seemed AWESOME! Those days are long gone. Now I’m standing in line for funnel cakes!

  • Reply Krystal // The Krystal Diaries September 6, 2017 at 8:57 pm

    Everything about your outfit is so perfect! I love the backpack and your hat.

    • Reply Kassy S. Randazzo September 7, 2017 at 9:38 am

      Thanks, girl! The backpack has been so handy!!

  • Reply Ana Ojha September 11, 2017 at 11:52 am

    What a beautiful outfit! I loved the way how you have styled it! The skirt looks absolutely gorgeous and you’re nailing your outfit!

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