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Chicago Fall Fits: Back-to-School Looks for Crisp Days
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items Fall in Chicago means layering up in the morning, shedding a hoodie by lunch, and dodging lakefront wind gusts on the walk home. Whether you're headed to high school in Humboldt Park or starting your first year at UIC or DePaul, these fall fashion pi...
Sections
8
The Layering Game
Denim Days
On the Move
Street to Classroom
Outerwear MVPs
Top It Off
The Layering Game
Stay cozy in classrooms and coffee shops with these knits made for Midwest mornings.
I’ve been living in this tie‑neck sweater latel! It’s effortlessly chic with a hint of preppy personality (the puff sleeves and keyhole tie detail are so fun!), and it layers perfectly under a coat or over a tee when Chicago mornings get cold.
Wool-Blend Puff-Sleeve Tie-Neck Sweater | Old Navy
I’ve fallen for this Maeve Cape Cardigan. It’s cozy and whimsical without feeling oversized, and the built-in collar adds polish to casual fall layers. It’s the perfect weight over tees or turtlenecks when Chicago mornings are crisp but midday still ...
Maeve Cape Cardigan Sweater
This striped pullover has quickly become my go-to cozy piece for fall- it’s soft, lightweight, and the bold contrast stripes elevate any look without feeling overdone. I love throwing it over a tee or beneath a chunky cardigan during crisp Chicago mo...
Striped Pullover Sweater
This cozy white pullover with cheerful little oranges is the kind of piece that sparks compliments in the elevator and joy in your mirror. It’s soft and perfectly oversized for a casual-chic fall look. Pair it with jeans or wide-leg pants and white s...
Womens Knitted Orange Sweater
I’ve totally fallen for this Better‑Than‑Wool cardigan—it feels like cashmere without the fuss, with the softest knit and just enough structure so it doesn’t swallow your frame. The mustard and pink sand stripes bring warm, preppy color to every outf...
Better-Than-Wool Cardigan - Mustard/Pink Sand Stripe
This pullover is a delightful twist on cozy fall style - the subtle sequin lips and retro ‘kissing booth’ lettering feel youthful and fun without ever being cheesy. I love layering it under a denim jacket on chilly Chicago mornings when you want a da...
Brandy Kissing Booth Sequined Pullover
Denim Days
Your fall wardrobe’s foundation: jeans that fit right, look good, and go everywhere.
These wide‑leg jeans have become a fall staple for me. They sit above the waist so everything feels super streamlined, and the drapey fabric gives all-day comfort. I love styling them under cozy sweaters or cropped cardigans as the weather shifts aro...
Extra High-Waisted Super Wide-Leg Jeans | Old Navy
These slim-flare jeans have become my go-to for fall. They hug at the waist and hips then gently flare from the knees, giving a polished campus-ready silhouette that still feels comfy thanks to their ultra-stretch fabric. Whether layered under cozy s...
Slim Flare Trouser Jeans | UNIQLO US
These Levi’s Barrel jeans have quickly become my fall denim uniform- the mid-rise hits just at the belly button, and the gentle barrel curve gives that relaxed yet polished vibe I’m all about. They’re roomy through the thigh and stack effortlessly ov...
Baggy Dad Barrel Women's Jeans | Levi's® US
On the Move
Comfort meets style—perfect for campus commutes and weekend hangs.
These sleek High‑Waisted SleekTech trousers have totally changed my fall rotation - they feel polished like office pants but are made from performance fabric with moisture-wicking, stretch, and all-day softness. Perfect for going from classroom to in...
High-Waisted SleekTech Trouser Pants | Old Navy
This pullover has quickly become my go-to for layering. It’s like wearing a cozy cloud with its ultra-soft Bounce Fleece fabric. The half-zip design lets you adjust for warmth, and the relaxed fit makes it perfect for throwing over a tee or under a j...
Half-Zip Bounce Fleece Pullover Sweatshirt | Old Navy
This Nimsruc jogger set is my go-to for early fall layering - it’s soft, stretchy, and the hoodie adds just the right amount of warmth without overheating. I love pairing it with a graphic tee and sneakers for a laid-back campus look, or layering it under a denim jacket when the wind picks up.
Nimsruc Women's Two Piece Jogging Suit
Street to Classroom
Boots made for the Red Line and those endless hallways.
I’ve been wearing the Esmee Lace‑Up boots on repeat on cool days. I love the classic UGG comfort mixed with a trendy platform. They’re as cozy as they are stylish!
UGG Women's Esmee Lace Up
These Chelsea boots have quickly become a favorite - so lightweight, yet the lug sole and cushioned insole keep me comfortable all day. I toss them on with jeans or sweater weather outfits.
Women's Northbound Chelsea Boot
These Amazon Essentials tall block‑heel boots surprised me with how comfortable and versitile they really are! They go with everything from skinny jeans and knits to midi dresses and chunky sweaters.
Amazon Essentials Women's Tall Block Heel Boots
These tall Miranda boots have become my go-to for fall - effortlessly cool with their Western-inspired silhouette and comfortable foam-cushioned insoles. They look just as great with wide-leg jeans as they do layered under a cozy dress or chunky swea...
Frye & Co. Miranda Western Boot
Outerwear MVPs
Because you need a jacket that slays and stays warm when the temp drops at 4 PM.
This patent moto jacket has become my chic go-to for fall- its glossy finish and candy‑pink hue instantly elevate any outfit, while the cropped cut layers perfectly over sweaters or hoodies. It’s the kind of bold piece that feels totally fresh stroll...
Maeve Patent Faux-Leather Moto Jacket
This cropped faux suede jacket has been my go-to for layering this fall -it’s soft, lightweight, and adds a touch of sophistication to any outfit. I love pairing it with high-waisted jeans and ankle boots for a chic, campus-ready look.
AUTOMET Womens Faux Leather Suede Jacket
This sherpa-lined hoodie is my go-to for chilly Chicago mornings - it’s warm, cozy, and the oversized fit makes layering a breeze. I love pairing it with leggings and boots for a casual campus look, or throwing it over a sweater when the wind picks u...
Vipwest Womens Fleece Jacket F
Top It Off
Scarf it up, hat it out—accessories that scream fall in the best way.
This scarf is officially my fall layering hero - it's impossibly soft (seriously, it feels like cashmere), yet lightweight enough to knot or drape without bulk. The classic plaid colorways bring polish to any outfit, and it's just cozy enough to shim...
Super Soft Classic Cashmere Feel Scarf
This charming crochet bucket hat brings a touch of vintage Parisian flair to your winter wardrobe. With its double-layer design - featuring a soft fleece lining and delicate floral accents - it offers both warmth and style, making it a cozy yet fashi...
French Thicken Women's Flowers Knitted Hat
With their starry patterns and cozy knit, these arm warmers offer both warmth and a pop of personality, making them a must-have accessory for the season.
Arm Warmers
One-and-Done Looks
Easy to wear, easy to layer—dresses that do it all.
This mini sweater dress feels like you’re slipping on a cloud, it's literally ‘SoSoft’ and so smooth, it practically hugs you. I love how it layers easily over a tee or turtleneck, or under a chunky cardigan or coat, ideal for those variable Chicago ...
SoSoft Sleeveless Mini Sweater Dress | Old Navy
This denim midi dress is my new favorite piece for fall - it’s the perfect balance of structured and breezy. The square neckline and seamed skirt add a touch of sophistication, while the flared silhouette keeps it comfortable for long days on campus....
Fit & Flare Sleeveless Denim Midi Dress | Old Navy
This jumpsuit is my fall go-to - it’s effortlessly chic and so comfortable. The V-neck and lantern sleeves add a touch of elegance, while the belt cinches the waist just right. I love pairing it with ankle boots and a cozy cardigan for a look that tr...
PRETTYGARDEN Women's Fall Jumpsuit
The Finishing Touch
Jewelry, bags, and extras that pull your whole look together.
This bag is affordable but a work horse - I have been using it for my daily commutes for over a year and its going strong. I love the pockets and the structure, so it looks professional when going to the office, but is easy to carry on a commute.
LOVEVOOK Laptop Backpack
These beaded earrings - pumpkin spice, turkeys, and other fall motifs - are so cute!
Beaded Fall Earrings
These retro oval sunglasses are totally on trend - are super durable too, if you throw them in your bag haphazardly like I find I do!
SOJOS Retro Oval Sunglasses