Saddle Up! How the street style crowd rocks cowboy fashion.

Horse girls, unite!
In case you missed it, today is National Cowboy Day (yee-haw!), and we’re celebrating not just with a big cowboy hat and boots, but with the best way to channel your inner KenGi: street style photos! Even if you don’t have a horse to complete the look, you can still get that side-saddle vibe and stock up on some essential horse girl gear—like breeches, jodhpurs, chaps, knee-high riding boots, or even a leather vest. Giddyup!
Saddle up and scroll through the photos below to see some of our favorite Western-inspired street style looks.

Milan, fall 2022 ready-to-wear
Photographed by Phil Oh

Florence, fall 2026 menswear
Photographed by Acielle / Style Du Monde

Paris, spring 2025 menswear
Photographed by Phil Oh

Florence, spring 2025 menswear
Photographed by Acielle / Style Du Monde

Paris, fall 2024 ready-to-wear
Photographed by Phil Oh

Milan, spring 2023 ready-to-wear

Paris, spring 2023 ready-to-wear
Photographed by Phil Oh

Paris, fall 2023 ready-to-wear

Frequently Asked Questions
Here is a list of FAQs about Saddle Up How the street style crowd rocks cowboy fashion covering beginner to advanced topics

Beginner Questions

Q What exactly is cowboy fashion in street style
A Its mixing classic Western pieces with modern everyday clothesnot full rodeo gear Think boots with a slip dress or a cowboy hat with a leather jacket

Q Do I need to own a horse to wear this style
A Absolutely not This is about borrowing the aesthetic not the lifestyle Youre using Western details to add personality to your outfit

Q Whats the easiest piece to start with
A A pair of cowboy boots They instantly add a cool factor to jeans skirts or even wideleg trousers Go for a classic brown or black leather for maximum versatility

Q Can I wear a cowboy hat in the city without looking like Im in costume
A Yes but keep the rest of your outfit modern and minimal Pair a felt hat with a trench coat and sneakers or a straw hat with a linen suit Avoid matching it with a full Western shirt and chaps

Advanced StyleSpecific Questions

Q How do I mix cowboy boots with feminine pieces
A This is the key to the street style look Try pointedtoe boots with a flowy midi dress a slip skirt or even a tailored mini skirt The contrast between tough boots and soft fabric is the goal

Q Whats the difference between a real cowboy boot and a fashion boot
A Real boots have a high angled heel and a pointed toe for riding Fashion boots often have a lower block heel rounded toe or chunkier sole for walking on pavement Street style usually favors the fashion version for comfort

Q How do I avoid looking like a country singer
A Skip the matching sets Instead pick one Western element as your focal point For example boots black jeans a plain white tee a tailored blazer No fringe no rhinestones

Q Can I wear bolo ties without a Western shirt