5 Best Jeans to Wear This Fall

Written by Bailey Williams
The fall candles are lit, the Pumpkin flavored treats line the grocery store aisles, and closets are changing as quickly as the leaves. Time to swap those shorts and sundresses for this season’s trendy fall finds. Last fall may have kept lots of us working from home in our leggings everyday, but as fall activities are opening up after a season of social hibernation, let’s not let the return of denim be what haunts us.
Wanting to shop but feeling like it’s trick-or-treat when you get to the store? We’ve got you covered for the best jeans to wear this season for every fall activity on your calendar. No shopping spookies here!

Madewell’s Balloon Jean
The Cozy Coffee Shop Jean
Find yourself still working from home but enjoying the flexibility of taking meetings from your neighborhood coffee shop? Trade those leggings and sweatshirt for a warm toned cardigan and Madewell’s top selling Balloon jean. It’s time to spice up the “work from home” attire but stay comfy and chic while checking emails over a PSL. You may even need to stand up in your zoom meeting so everyone can check out these pants.
Try pairing the Corson wash with a burnt orange cardigan or beige oversized sweater. A pair of cute loafers or casual tennis shoes will do the trick to pull this look together.
Madewell’s Cali Demi-Boot Jean in Edmund Wash
The Halloween Horror Nights Jean
Looking for a pair of staple black jeans for a night out? These Madewell Call Demi-Demi Boot jeans offer a mix of classy yet edgy style to any look. Perfect for that Harry Styles concert on Friday or Saturday night at the Haunted House. Pair with a shiny top and leather jacket or striped tee and booties and you’re set.
Shopping at Madewell for these looks? Don’t forget these deals are all treat and no trick:
- 15% for student, teacher, and health care workers when you shop in store
- $20 off a new pair when you bring a worn pair of jeans
- Curvy, maternity, tall and petite sizes available
Everlane’s ‘90s Cheeky Jean in Patched Wash
The Pumpkin Patch Jean
Wear these vintage-inspired pants with a striped turtleneck under an oversized sweater and you have the perfect pumpkin patch look. If your weekend plans include taking the train upstate to see the fall foliage or walking around the neighborhood looking at Halloween decor, these classic Everlane pants are a go-to denim favorite. Comfy and easy to pair with casual tops and sweaters, we’re buying the ‘90s Cheeky Jean in multiple washes.
10% off at Everlane if you sign up for an account with your email.
Levi’s High Rise Cropped Flare
The Weekend Adventurer Jean
Apple picking outfit? Consider it picked. Honey, you’re gonna look crisp in these. A High Rise Cropped Flare is making a comeback and deserves a spot in every denim drawer. These Levi’s are as classic as this fall activity and make the perfect pant for a casual yet festive outing. Partner with a cute blouse and bomber jacket or fitted turtleneck to highlight the shape of these pants.
- 30% off Friends and Family event happening this fall and vintage resale jeans available online
- Student teach discount available with student ID
Zara’s Tailored Straight Leg
The Home for the Holidays Jean
Booked your flights home for the holidays? This classic denim is perfect for a family gathering around the table or an evening Friendsgiving. Pair with booties and a blouse or platform loafers and blazer. You’ll look family friendly and wine and dine ready. Accessory: pie.
Getting back to shopping can be an overwhelming task after months of being inside. We hope this quick cheat sheet to the season’s best jeans helps the shopping become less trick and more treat.
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