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Instagram Roundup September 2025

Happy October! Today is the first day it actually feels like Fall and I am loving it. It has been hot here in WI and these cooler temperatures feel very refreshing. Here are the top 5 looks you all loved the most on Instagram last month!

#1. I styled one of my favorite cotton summer dresses for Fall with a cute cardigan and one of my favorite pairs of tennis shoe.

L.L.Bean 1912 Heritage Mockneck Cardigan (similar, mine is old)

Chicwish Tropical Fruit Dreamland Cotton Midi Dress

Keds Champion Point Low Wave Perforated Leather Jute Foxing Tennis Shoe

#2. This was a church look last month and you all loved it! I styled my favorite black linen skirt with a fun J.Crew top and my favorite jelly flats.

Siliteelon Gingham Button Down (similar, mind is old)

Not Perfect Linen Sion Gathered A-Line Skirt

Sam Edelman Michaela Jelly Mary Jane Flat

Fasoty 9 Pcs Gold Hair Ties

#3. I will always love a plaid skirt for Fall. Add a cute pumpkin sweater and I’m all in!

Kiel Jame Patrick Cozy Pumpkin Fair Isle Sweater

Chicwish Plaid Tweed Midi Skirt

Moda Luxe Harper Crossbody

Steve Madden Belinda Flats (different color way, mine are old)

#4. I love this dress for early Fall because it has a Fall feel but is still cool enough to wear when it’s hot outside.

Quotes and Cotton Leopard Print Maxi Dress

Steve Madden Belinda Flats (different color way, mine are old)

#5. Another cotton summer dress I have been wearing into Fall. I love the eyelet pattern and it’s very cute paired with tennis shoes!

Chicwish Sunny Poise Embroidered Midi Dress

Keds Champion Point Low Wave Perforated Leather Jute Foxing Tennis Shoe

Which look is your favorite? Leave a comment, I would love to read it! And make sure to sign up for emails, and follow me on Instagram, LTK and Pinterest for all of my latest posts!

~Caitlin~

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