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Midsize Style Guide: Cute & Cozy Fall Pieces 🍂

Purple Star emoji 10 items
Finding stylish fall outfits as a midsize girl can sometimes feel tricky, so I put together this guide full of cute and cozy pieces that actually flatter and feel comfortable. These looks are perfect for crisp autumn days, whether you’re heading to t...
Sections
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Comfy Two Piece Sets

Fall two-piece outfits that make getting dressed simple and stylish. These sets are cozy, flattering, and easy to throw on, giving you that effortless look without overthinking your outfit.
 
Kayla Tolosi profile picture
I am obsessed with this striped set. I got the dusty blue color in an XL. I love the oversized look for extra comfort. I would recommend sizing down for a slightly snugger look if desired.
LILLUSORY 2 Piece Sets Women 2025 Fall

Basic Bottoms

Everyday bottoms that are comfortable, versatile, and easy to style. From classic jeans to cozy leggings, these pieces make putting together effortless outfits simple and stylish.
 
Kayla Tolosi profile picture
Hear me out - as a midsized girly I didn’t think these would look good but they are so cute! As a die hard skinny jean girly this was a bold choice but i absolutely love the fit of these. I can dress them up for work too. They are high waisted so per...
High-Waisted Canvas Barrel Ankle Pants
 
Kayla Tolosi profile picture
Leggings are a non negotiable for me especially during the fall months. I have worn these leggings for at least 15 years - if I’m in leggings they are always going to be the Aerie OG! Super soft and comfortable - I love the high waisted for tummy con...
OFFLINE By Aerie OG High Waisted Legging
 
Kayla Tolosi profile picture
These are just like the other Old Navy Barrel jeans but slightly thicker. Perfect for cooler weather and versatile.
High-Waisted Barrel Ankle Jeans - Old Navy - Gap

Cozy Tops

Cozy and stylish tops that are perfect for everyday wear. Soft, comfortable, and effortlessly trendy, these pieces make it easy to look put-together while staying relaxed.
 
Kayla Tolosi profile picture
If you know me, you know I live in anything aerie waffle knit. This is a top you can dress up with jeans or dressy down with leggings. Size L was the perfect fit for me.
AE Big Hug Waffle Sweatshirt
 
Kayla Tolosi profile picture
Having a flannel in the fall is my go-to layering top. This flannel is super soft with an oversized pocket on the chest. So many outfit options - I got size L.
Aerie Anytime Fave Flannel Button Down Shirt
 
Kayla Tolosi profile picture
A Free People dupe for fall. There are so many different color options. I love the baggy casual look of this top - perfect for leggings and cute sneakers. I got a size L.
UEU Women Striped Oversized Color Block Sweatshirt

Shoes

 
Kayla Tolosi profile picture
These are so comfortable! A classic versatile shoe that goes with any fall outfit. Many different color options - my favorite is the white and black two tone.
Nita Platform Sneakers | Women's Memory Foam Comfort
 
Kayla Tolosi profile picture
I have so many pairs of embroidered high tops from Converse. I love to wear them with my jeans or leggings in the fall. The embroidered look is by far my favorite.
Chuck Taylor All Star Lift Platform Embroidered Flowers Women's ...
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Kayla Tolosi profile picture
A staple during fall for me every wear. I love my black stompers all during fall into the winter.
Delta Black Chelsea Boot
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