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5 Chic Transitional Outfit Ideas With Jeans to Wear Into Fall
Fashion

5 Chic Transitional Outfit Ideas With Jeans to Wear Into Fall

by jummy84 August 28, 2025
written by jummy84

There’s no denying that I am a fall girl at heart and I couldn’t be more excited that it is now just around the corner. To prep for the upcoming end-of-summer moments, I set out to find some fresh transitional outfit inspiration to help guide my wardrobe for the upcoming season, with a special focus on denim. I turned to some of my favorite Instagram fashion follows to start informing my next shopping trip.

Below, you can peruse and shop five chic outfits with jeans that are perfect for wearing now straight into fall. These inspiring ensembles span from stylish muses in Stockholm, Paris, and London. Each look incorporates cool denim styles like straight-legs and baggy options alongside some classic basics and trendy accessories—think standout necklaces and flip-flop sandals.

Outfit #1

Get the Look

Pima Cotton Blend Crewneck T-Shirt

Nordstrom

Pima Cotton Blend Crewneck T-Shirt

Long Double-Breasted Trench Coat - Women | Mango Usa

MANGO

Long Double-Breasted Trench Coat

Shoulder Bag

Levi, 501® Original Cropped Women's Jeans

Levi’s

501 Original Cropped Jeans

By Anthropologie Thong Kitten Heels

By Anthropologie

Thong Kitten Heels

The sandal trend of the moment.

Outfit #2

Swedish fashion pr and influencer Johanna Lager poses for a mirror selfie wearing a red beaded necklace, brown T-shirt, oversize black blazer, thin black belt, white wide-leg jeans, and black pointed-toe shoes

Get the Look

Oversize Luxe Twill Jacket

Kenneth Cole

Oversize Luxe Twill Jacket

SHASHI, Rojo Necklace

(re)generative Cotton Ribbed Scoopneck Tank

Madewell

(re)generative Cotton Ribbed Scoopneck Tank

Brown basics are having a moment.

J.Crew, Skinny Oval Buckle Leather Belt

J.Crew

Skinny Oval Buckle Leather Belt

Low Slung Baggy Jeans

Madewell

Low Slung Baggy Jeans

I’m a fan of white jeans no matter the season.

Reynna Pointed Toe Slingback Pump

Marc Fisher LTD

Reynna Pointed Toe Slingback Pump

Outfit #3

British plus size style influencer Abisola Omole poses on a sidewalk during Copenhagen Fashion Week wearing a blue button-down shirt, white basic top, faded Madewell straight-leg jeans with raw hems, and pointed cap-toe Miu Miu slingback kitten heels, and a bamboo top-handle mini bag

Get the Look

Trestles Twill Button-Up Shirt

Vuori

Trestles Twill Button-Up Shirt

So many styling possibilities.

Crewneck T-Shirt

Nordstrom

Crewneck T-Shirt

Bamboo Leather Tote

JIL SANDER

Bamboo Leather Tote

The Plus Darted Barrel-Leg Jean

Madewell

The Plus Darted Barrel-Leg Jean

You can’t go wrong with Madewell jeans.

MOTIMODEN, Pointed Kitten-Heel Slingbacks

MOTIMODEN

Pointed Kitten-Heel Slingbacks

These instantly elevate any look.

Outfit #4

British fashion influencer Anna Newton poses for a mirror selfie in her cool London closet wearing a white T-shirt, green sweater tied around her waist, a black Loewe puzzle bag, relaxed white jeans, and black flat flip-flop sandals

Get the Look

Interlock Short Sleeve T-Shirt

ZARA

Interlock Short Sleeve T-Shirt

Crewneck Sweater

Vince Camuto

Crewneck Sweater

Loewe, Small Puzzle Edge Bag

Loewe

Small Puzzle Edge Bag

Good Standard Baggy Jeans

Good American

Good Standard Baggy Jeans

Havaianas, Slim Flip Flop

Outfit #5

British style influencer Marilyn Nwawulor-Kazemaks poses for a mirror selfie in her London living room wearing a black linen button-down shirt, shell pendant necklace, cropped ankle-length straight-leg jeans, a small brown suede tote bag, and The Row black and red flip-flop sandals

Get the Look

100% Linen Oversized Shirt

Gap

100% Linen Oversized Shirt

A linen button-down is always a good idea.

Bundle Black Shell Necklace

Heaven Mayhem

Bundle Black Shell Necklace

Split Leather Bowling Bag

ZARA

Split Leather Bowling Bag

Levi's, 501 Original Cropped Jeans

Levi’s

501 Original Cropped Jeans

Yellhum, Flip Flop Sandals

Yellhum

Flip-Flop Sandals

The perfect pop of color.

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