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14 Best Saddle Shoes for Men: A Timeless Classic Reinvented

CEO Tinh Phung
Source: AMBROGIO I remember wearing saddle shoes with my school uniform for years. When I went off to college, I was relieved to never have to wear them again. But, unexpectedly, I started to miss...

Best Saddle Shoes For Men Source: AMBROGIO

I remember wearing saddle shoes with my school uniform for years. When I went off to college, I was relieved to never have to wear them again. But, unexpectedly, I started to miss them.

It didn’t help that in the aughts, Ivy Prep was making a comeback. Gossip Girl was huge. Anna Wintour approved of J.Crew. Saddle shoes were being styled in new and cool contexts that didn’t always include khakis and a club tie.

These days, saddle shoes represent a gamut of aesthetics. Traditional versions can be styled classically or in a fun, madcap way. They’ve been remixed into a range of contemporary styles, including ones that make them more understatedly modern or add color and details for an "irreverent golfer" look.

Let’s delve into the world of these classic menswear staples and explore a few choice models.

What Are Saddle Shoes?

Saddle shoes are a style of Oxford shoe with a closed lacing system and a noticeably separate cut of leather sitting on top, resembling a saddle. Traditionally, the saddle is in a contrasting color, while the plain toe and back are often white. These shoes have a slightly lower heel than dress Oxfords and were historically worn by both women and men.

A Brief History of Saddle Shoes

Saddle shoes were introduced in 1906 as indoor footwear and quickly became popular among school children in the 1930s. They were later embraced by stylish teenage girls known as bobby soxers in the 1940s. The shoes found their way into the swing dance and rockabilly scenes and even made appearances in pop culture, such as in Elvis Presley's Jailhouse Rock.

Today, saddle shoes continue to evoke nostalgia, youth, and vintage subcultures. They have been featured in various TV shows, including Twin Peaks, Family Matters, and The Gilmore Girls.

The Best Saddle Shoes for Men

Saddle shoes now represent a wider range of personal styles. Here are 14 gamut-running pairs to consider:

Crockett & Jones The Bosham Saddle Shoe

The Bosham Shoe balances the classic saddle design with non-traditional features. It's a Derby shoe, allowing the saddle to stand out, and the body is understated, making it suitable for various outfits. Made by Crockett & Jones, a renowned shoemaker from England, these shoes are handcrafted and Goodyear-welted.

Crockett and Jones The Bosham Saddle Shoe Crockett & Jones The Bosham Saddle Shoe

Sherman Brothers Alden Saddle Shoe

The Alden Saddle from Sherman Brothers Shoes combines casual-leaning details with a monochrome palette. Made from shell cordovan leather, known for its durability and beauty , these shoes add elegance to relaxed outfits.

Sherman Brothers Alden Saddle Shoe Sherman Brothers Alden Saddle Shoe

Cole Haan Air Colton

Cole Haan's Air Colton played a significant role in bringing saddle shoes back into fashion. With its comfortable and dressy leather-rubber sole and sleek design, this shoe is a versatile choice.

Cole Haan Air Colton Cole Haan Air Colton

T.B. Phelps David Oxford

The David Oxford by T.B. Phelps is a true saddle shoe, combining hand-sewn construction with premium leather. These shoes conform to your feet, making them exceptionally comfortable.

T.B. Phelps David Oxford T.B. Phelps David Oxford

Johnston & Murphy Conard Saddle

The Conard Saddle by Johnston & Murphy offers more than just a budget-friendly price. With its flat saddle, stacked outsole, formal heel, and subtle coloring, this shoe strikes a balance between tradition and modernity.

Johnston and Murphy Conard Saddle Johnston & Murphy Conard Saddle

Cole Haan ØriginalGrand Saddle

The ØriginalGrand from Cole Haan is a modern golf shoe with high-traction tread and a wavy saddle design. These shoes are waterproof and comfortable, making them perfect for both casual wear and the golf course.

Cole Haan OriginalGrand Saddle Cole Haan ØriginalGrand Saddle

Crockett & Jones The Princeton Saddle Shoe

Crockett & Jones takes an authentic saddle shoe design and combines it with high-end Goodyear-welted craftsmanship. The Princeton Saddle Shoe features stark black and white contrasts and a refined nubuck leather.

Crockett and Jones The Princeton Saddle Shoe Crockett & Jones The Princeton Saddle Shoe

Grenson Bellamy

Grenson's Bellamy saddle shoe showcases a thicker silhouette and a more casual look. Made from premium leather and Goodyear welted, these shoes are built to last.

Grenson Bellamy Grenson Bellamy

Bolano Elwyn Oxford Wingtip

For those who love bold fashion, the Bolano Elwyn Oxford Wingtip is an undeniably loud shoe. With its swing dance-inspired design and vibrant accents, this shoe makes a strong statement.

Bolano Elwyn Oxford Wingtip Bolano Elwyn Oxford Wingtip

Allen Edmonds Shelton (Discontinued)

The discontinued Allen Edmonds Shelton is a legendary shoe in a burgundy colorway. Its simple aesthetic and subtle contrast make it versatile and sophisticated.

Allen Edmonds Shelton Allen Edmonds Shelton (Discontinued)

Paul Smith Sonnet Oxford

The Paul Smith Sonnet Oxford adds a playful touch to the classic saddle shoe with orange accents. Made in Italy from 100% calf leather, this shoe is both classy and fun.

Paul Smith Sonnet Oxford Paul Smith Sonnet Oxford

Ambrogio Bespoke Saddle Oxford

For the ultimate in luxury, the Ambrogio Bespoke Saddle Oxford merges Italian craftsmanship with the classic saddle shoe design. Hand-painted by artisans in Spain, this shoe exudes elegance and refinement.

Ambrogio Bespoke Saddle Oxford Ambrogio Bespoke Saddle Oxford

August Apparel Lincoln Ave Line

The August Apparel Lincoln Ave Line offers a range of saddle shoe styles. From traditional black and white options to highly formal patent leather versions, these shoes cater to various tastes.

August Apparel Lincoln Ave Line August Apparel Lincoln Ave

These saddle shoes represent a perfect blend of tradition and modernity. Whether you prefer a classic look or want to make a bold fashion statement, there is a saddle shoe for you.

FAQs

Why were they called saddle shoes? The decorative panel on the middle of the shoe resembles a saddle on a mount.

What year were saddle shoes popular? Saddle shoes reached their peak popularity in the 1950s and '60s but have remained a classic footwear choice.

Are saddle shoes still in style? While they may not be considered "hip" at the moment, saddle shoes are classic and unlikely to go out of style any time soon.

In conclusion, if you're looking for authentic saddle shoes, Grenson and Crockett & Jones offer excellent options. For a more modern and practical take, Cole Haan is the way to go. Whether you prefer subtle elegance or bold fashion, there is a saddle shoe out there waiting for you.

Have you ever worn saddle shoes? Let me know in the comment section!

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