Outfit Inspo for 4 Favorite Fall Activities

Fall is definitely my favorite time of the year. It is a time for fun activities, enjoying the outdoors, fall colors! October is also my birthday month, so naturally, I am just drawn to fall activities. Below I listed some of my favorite fall activities and some outfit inspo to help you find the perfect outfit to wear this season!


Pumpkin Patch

One thing that I always look forward to is heading to some of our local farms to take part in

their fall activities and picking out the perfect pumpkins. Since I am usually chasing around children and picking up dirty gourds, I am looking for comfort and durability when I am getting dressed.

I picked up this amazing flannel shirt from Old Navy. It is light weight, warm, and the perfect color for fall (they have several other patterns as well). I paired it with a pair of my jean shorts and my Birkenstock sandals because fall in Maryland means mid 70's. As the weather gets colder, this shirt would also look adorable with a pair of jeans and booties!




Wine Tasting

There is nothing better than sitting outside, enjoying the fall foliage and drinking some tasty wine. Every year my husband and I visit our favorite local wineries for our anniversary. I try my best to be practical while still trying to maintain a cute and casual look.

This sweater from one of my favorite boutiques is perfect for this occasion (Check out Simplee Sweet Boutique and use code Chessie15 for 15% off your purchase!). The fun print makes it super stylish and the material is so soft and warm. A visit to the winery is the perfect excuse to wear my favorite shoe purchase of this season. These Steve Madden Mules are absolutely adorable. Talk about mixing comfortable and stylish! I will be wearing these EVERYWHERE I can this year! Perfect for wanting to look cute while planning on doing some walking around the vineyard. I started off wearing this sweater with my denim shorts, but as the weather cools off I would definitely either pair with a cute pair of jeans or my vegan leather leggings!




Outdoor Dining

Once that weather breaks and it is finally not 90 degrees with 100% humidity, I love to start dining outside. In our area it is important to wear layers.

It tends to drop in temperature rather quickly and you could end up either starting very hot or ending up very cold.

These animal print pants from Amazon are going to be perfect for those nights. These paper bag waist pants are lightweight but provide the leg coverage you will need when it cools off. Because the pants are printed I really wanted to find a good tee that I could wear with them. I




ended up finding this designer inspired shirt from Always Stylish Mama which worked perfection. If I needed to be a little warmer I could bring a sweater or a denim jacket that could easily be put over top!





Haunted Houses



Ok, so I may be alone in loving haunted houses and being scared stiff, but I can say this outfit could also be good for the entire Spooky season! My favorite boutique (Simplee Sweet Boutique) has the best inventory of shirts for the spooky season. (use code Chessie15 for 15% off your order!)

I happened to choose the dancing skeletons because it was spooky and silly at the same time. I figured beyond wearing this to the haunted house, I could also wear it to school for Halloween. I also picked up this great pair of distressed leggings from Mint Julep Boutique They are buttery soft and super stretchy (I absolutely hate when leggings are stiff). Depending on the weather these leggings would go with sneakers or my Hunter rainboots.








I hope that you found some future inspo for your future fall activities! If you want to check out some of my other looks head over to Chessiebaystyle on both Instagram and Liketoknow.it! Thanks for reading lovies! Have a happy and healthy fall!

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