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Cassie Brady

effortlessly chic style for the everyday woman

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in Fall, Fashion, outfit of the week · November 2, 2020

How To Wear A Maxi Dress In The Fall

Maxi dress

A maxi dress is one of my favorite things to wear thanks to its simplicity. Just throw one on and go. Not much mixing and matching required besides adding in a few accessories. With fall in full swing I couldn’t help but add a new maxi dress to my wardrobe.

Outfit Details: Dressbarn Dress & Earrings (similar here) c/o, Guess Booties (similar here, & here)

Maxi dress

This Dressbarn maxi checks all the boxes when it comes to effortless fall dresses. I love the muted floral pattern, the long length, and how great this dress looks when worn with boots or layered with a cozy cardigan.

fall floral dress
Add A Layer

I typically don’t wear maxi dresses in the fall, but this year I can’t get enough of them! I love wearing them alone like I did here or when it’s chilly out I’ll layer a cozy sweater or cardigan over them. This cardigan is one of my favorites for layering over dresses. Style Tip: when layering a sweater or cardigan over a dress that dress will instantly look like a skirt, essentially doubling your wardrobe.

maxi dress
Wear Boots

Another way to wear maxi dresses in the fall is to style them with boots. My brown ankle boots (similar here, & here) when paired with this floral maxi dress gives off a rustic earthy vibe perfect for fall.

maxi dress
fall floral outfit
women's fall outfit
Dressbarn floral print
Dressbarn outfit
Womens fall outfit

For more fall dress inspiration check out this dress I wore to a fall wedding last year and this dark moody floral dress I wore a two years ago.

Previous Post: « Monthly Style Diary: August 2020
Next Post: How To Recreate My Go To Fall Outfit »

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Hi there! I'm Cassie, a fashion and lifestyle blogger located in the Midwest. I love fashion, photography, & working from home with my dog on my lap. On this site you'll find fashion, travel, and home decor inspiration to help you feel more confident in the clothing you wear, trips you take, and home you create. Thank you so much for stopping by! x Cassie

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My Mother’s Day started at 4am with a nursing baby My Mother’s Day started at 4am with a nursing baby in my arms, a toddler crawling into my bed and falling asleep on my shoulder, & a doggie sleeping across my legs. 💕 They have no idea what today is, but I’m feeling so blessed to be surrounded by all my babies on Mother’s Day 👶🐶👧 Even if it was at 4am 🥱

Not pictured our dog Sydney. 🐶 I’m so tired I didn’t even notice until after we got these pictures 🤪 I knew I was forgetting something! 🙈
Color coordinating with my son for a quick photo s Color coordinating with my son for a quick photo shoot before going home 📸🧸 His going home outfit, sign, & blanket are from @cadenlane & I bought a button front nightgown to match from @amazon in brown 🤎
He’s here! 🥲💙 Henry Patrick Brady April 7th, 2026 He’s here! 🥲💙
Henry Patrick Brady
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So thankful my SIL @thedivinemissem77 answered her phone and came quickly to stay with Audrey & my hubby @npbrady9 taking care of everything else as we rushed to the hospital. ♥️ God is so good & we couldn’t be happier with the newest member of our family 🤗
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Wearing a pregnancy/nursing dress from @amazon & The comfiest shoes for my swollen feet from @birdies 💕
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