As much as I love a trendy shoe, some outfits just work best with something a bit more classic, and yes, boring. It’s not just me—the favoritism of “boring” shoes is something I’ve been noticing out in the wild as well. An outfit that’s paired with anti-trend winter shoes is something I always clock. And more often than not, said outfit contains other equally classic pieces. Speaking of, I’m here to discuss a specific pairing I’ve spotted over and over lately: straight-leg jeans with low-heel ankle boots. (To add to the boringness, the boots are often simple black leather ones.)
Straight-leg jeans look chic with a myriad of current shoe trends, so the choice to pass them by is significant. In particular, I like that the combination doesn’t compete with the rest of your outfit, and this time of year, our layered outfits can consist of many different pieces. I rounded up a few looks from this season that drive my point home and found a handful of straight-leg jeans and low-heel ankle boots to pair together. Scroll for outfit and shopping inspiration of this classic combination.

Outfit tip: A plaid shirt tied around your waist is the most 2025 way to wear the jeans-and-boots combination.

Outfit tip: Add a scarf coat for a dose of drama and elegance.

Outfit tip: Denim-on-denim looks especially chic when paired with burgundy ankle boots.

Outfit tip: If you’d rather not look too boring, accessorize with a studded leather belt.

Outfit tip: Adding a brown suede jacket will ensure you get all the compliments your heart desires.
Shop Low-Heel Ankle Boots

Madewell
The Emilie Ankle Boots

Toteme
Slim Glossy Leather Ankle Boots

Reformation
Roberta Ankle Boots



ZARA
Leather Cowboy Ankle Boots

Everlane
Studio Kitten Heel Booties


Madewell
The Lexie Ankle Boots in Leather

The Row
Liisa Pointed Toe Booties
Shop Straight-Leg Jeans

Madewell
The Longline Straight Jeans

Reformation
Jax Super High Waist Straight Leg Jeans



Nordstrom
High Waist Straight Leg Jeans

Madewell
Perfect Vintage Wide-Leg Jean in SoftDrape

J.Crew
Nipped Straight Jeans

DL1961
Halle Straight Instasculpt High Rise Jeans

Agolde
Harper Jeans Mid Rise Relaxed Straight Jeans

