Baggy jeans are a must-have if you don’t want to wear only skirts and shorts in the summer, but there are also several reasons why they are a great addition to your winter wardrobe. From a practical standpoint, they can be easily worn over leggings on particularly cold days; from a stylistic standpoint, they give long, structured coats and knit sweaters an effortlessly cool look.
Baggy jeans also pair well with many of the top shoe trends of 2026, such as slouchy boots, ballerina sneakers, and even peep-toes that show off colorful and contrasting socks. Lug soles add a utilitarian touch to jeans, while cowboy boots emphasize their inherently relaxed vibe. Pointed shoes, whether heeled or square-toed ballerinas, add structure to the loose silhouette, pairing well with winter staples like oversized Oxford shirts and wool blazers.
Below, you’ll find the best shoes to wear with baggy jeans in winter, with reference photos to inspire you, whatever your style.
1.Strappy Slingbacks
Everything about this outfit is extravagant in the best possible way: the lambskin-lined coat, the oversized dark jeans, and the elegant patent leather buckles on these white slingbacks. They are paired with matching white socks, but we strongly recommend trying a pair in cherry red or delicate lavender to make the outfit even more interesting.
2.Lug-Sole Sneakers
With the faded black wash of these baggy jeans, the muted colors of the sweater, and the chunky black shoes, this outfit shows how to translate elements of 90s grunge style into 2026. Lug soles are particularly well suited to baggy jeans on icy days.
3.Slouchy Boots
Slouchy boots complement the casual look of baggy jeans. Here, the entire look is softened by a hint of lace peeking out between a black knit sweater and light blue jeans.
4.Skinny Sneakers
This denim-on-denim outfit features color accents throughout, from the picturesque prints on the silk scarf to the berry-colored bag and the bright blue racing stripes on these slim sneakers. They hug the foot like ballerina flats but are much easier to break in.
5.Pointed-Toe Flats
Baggy jeans are a classic, but paired with a blazer with pronounced shoulders, sporty sunglasses, and pointed ballerina flats, they suddenly take on a futuristic new look. A black pair goes well with both dark and light jeans, as well as styles with eye-catching patterns.
6.Cowboy Boots
When in doubt, add workwear. Cowboy boots are not only practical, they also emphasize the casualness of baggy jeans and contrast with the bold indigo wash of this model.
7.Pop of Color
These quilted jeans with glittering rhinestone appliqués deserve equally playful and unusual footwear. We found these ice blue mules that taper downwards, form an arch, and finally land on a solid base with pleasantly chunky block heels.
