What are saddle shoes? Which ones should you buy? This guide will answer your questions!
I wore saddle shoes with my school uniform for years. When I went off to college, I was relieved to never have to wear them again. Then, unexpectedly, I started to miss them.
It didn’t help that it was the aughts and Ivy Prep was making a comeback in a big way. Gossip Girl was huge. Anna Wintour had a new-found approval for J.Crew. Saddle shoes were being styled in new, 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 learn a bit more about these classic menswear staple and then look at a few choice models.
What Are Saddle Shoes?
Saddle shoes are a style of Oxford shoe, meaning they have a closed lacing system in which the eyelet tabs sit beneath the vamp. What distinguishes saddle Oxfords is that they have a noticeably separate cut of leather sitting on top of the middle part of the foot.
This decorative panel resembles a saddle, which is where it gets its name from. Often, but not always, the saddle is in a contrasting color. Traditionally, it would be black, navy, or even brown, while the plain toe and back would often be white.
Historically, these shoes have a slightly lower heel than dress Oxfords and were worn by both women and men.
A Brief History of Saddle Shoes
Saddle shoes came out in 1906, released by A.G. Spalding as indoor footwear, hence the lower heel and rubber outsole. By the 1930s, their indoor-friendly design made them a go-to shoe for school children, which is why, to this day, they’re associated with a youthful style.
In the ‘40s, stylish teenage girls who wore saddle shoes with ankle socks came to be known as bobby soxers, the original cool girls of the 20th century.
Since these shoes were so lightweight, they became popular among swing dancers, before making their way into the rockabilly scene. In 1957, Elvis Presley wore saddles in Jailhouse Rock.
Even in post-80s pop culture, saddle shoes were used as a symbol of nostalgia, youth, and vintage subcultures.
Some TV examples include Audrey Horne in Twin Peaks, Steve Urkel in Family Matters, and Rory Gilmore in The Gilmore Girls. Gossip Girl’s Chuck Bass even wears a pair, with argyle socks and an argyle sweater, during a croquet scene in the Hamptons.
Here are our top recommendations from the list:
Thanks to its understated aesthetic and subtle contrast, this shoe seamlessly blends with a range of personal styles, making it a wardrobe staple for the modern individual. Combining timeless design with everyday comfort, this legendary shoe is the perfect addition to your footwear collection.
Make a statement with these bold and undeniably loud shoes that exude vintage swing dance club vibes from the 40s. With a budget-friendly price tag of just $80, this daring footwear falls well within the easy experimentation price range.
Read on for more info and the complete list…
The Best Saddles Shoes for Men
And proving that modern-day saddle shoes represent a wider range of personal styles than the subcultures they’re often associated with, here are 14 gamut-running pairs:
Crockett & Jones The Bosham Saddle Shoe
The Bosham Shoe balances the classic saddle design with some non-traditional features.
First off, it’s a Derby, not an Oxford, which means it’s an open-lacing system. This allows the saddle to really stick out. Second, to balance this out, the rest of the body is an understated canvas.
The result is a confidently smart casual shoe that can be worn with khakis, jeans, and even a summer suit.
England’s Crockett & Jones is one of the few still authentically Savile Row style shoemakers that serve up truly hand-crafted, Goodyear-welted footwear.
Everything is made in Northampton in the UK, and they even do shoe repairs at that very same factory. Fortunately, you can order these shoes from Ben Silver in none other than Charleston, South Carolina.
The Bosham is built on Crockett & Jones’ 241 last, which has a moderately round toe, isn’t too long, and has that versatile English heritage character.
Sherman Brothers Alden Saddle Shoe
Another example of clever aesthetic balances, the Alden Saddle from Philadelphia-based Sherman Brothers Shoes features loads of casual-leaning details.
The broguing on the saddle’s edges carries on into the eyelet area, while the taper and arched toe are ever so slight. All of this allows you to wear these shoes with relaxed outfits, bringing a touch of elegance to them.
However, the monochrome palette, a departure from typical saddle shoes, anchors the entire shoe into a more formal look. Even more, it’s made out of shell cordovan leather, which is made from a horse’s hindquarters. It’s incredibly dense, making it super durable and undeniably beautiful.
In fact, shell cordovan is so resistant to stretching, it ripples instead of creases. Expect to contribute some break-in time to this shoe though.
Cole Haan Air Colton
Some might argue that it was Cole Haan’s Air Colton that made saddle shoes wearable (i.e. non-costumey) again.
In 2010, again during the preppy resurgence, GQ endorsed this model as the one that was bringing saddle shoes back. I definitely had a pair.
While the saddle shoe’s hipness was short-lived, its classic status remained. The sole is both leather and rubber, making them both comfortable and dressy — as does the Nike AIR technology it’s invisibly infused with (this isn’t one of those hybrid-looking shoes).
The shape is thin and elegant, and it comes in a versatile black and gray nubuck, as well as a fun and fashion-forward orange and gingersnap-like brown.
T.B. Phelps David Oxford
Definitely a time capsule of the saddle shoe’s heyday, the David Oxford by T.B. Phelps is a true saddle.
This may then make you wonder, why’s it for me then? I’m not a schoolboy in the ‘50s and I don’t play croquet.
Well, first of all, if you do play croquet, the David’s hand-sewn construction allows it to conform to your foot. If you don’t play croquet, this essentially means that the last is your actual foot. This is one comfortable shoe.
The leather is beautifully grained, while the suede is excellently napped.
At most, this shoe is impressive because it exists, and we can’t do a saddle shoe round-up without including what might be the last true, accurate descendant of the original saddles.
Johnston & Murphy Conard Saddle
In my review of the Johnston & Murphy brand overall, I called the Conard a budget shoe plus. At around $119, it’s in the same price bracket as a lot of budget shoes but has a lot more to offer.
It’s a true saddle shoe but doesn’t look like a complete throwback because of the flat saddle which makes the silhouette less bumpy, the stacked outsole and formal heel, and the coloring.
The contrast isn’t that dramatic, and there’s a slight and gradual patination on the toe that’s the same vivid brown on the saddle. They’re also comfortable and lithe, making them perfect for the dance floor at a wedding.
And while the leather is understandably thin, given its price point, it’s still made out of Italian calfskin, giving it a pleasant smell and handfeel.
Cole Haan ØriginalGrand Saddle
Technically, the ØriginalGrand from Cole Haan is a golf shoe and an excellent one at that. However, it’s a modern innovation, featuring a light and cushiony EVA midsole and a spikeless outsole.
In place of the spikes is high-traction tread, which means you can wear these shoes like
On the style side of things, this shoe hat-tips to the traditional saddle shoes, with the back broguing and the wavy saddle in the middle. The croc-embossing on the saddle definitely gives it a more fashion-forward vibe, similar to the Gucci Aces.
Unlike high-end designer
Cole Haan ØriginalGrand Remastered
This rendition of Cole Haan’s ØriginalGrand is a creative and dandier remix to the core version we just highlighted.
The “saddle” stops short of the halfway point from the top of the shoe, leaving some room between it and the wing-tip suede detail, making it more of a vest and belt than a saddle.
It’s just as comfortable and functionally sneaker-like as the regular ØriginalGrand, but is a lot splashier. The black and ivory version is closest to the traditional saddle shoe look, while the Silent Storm variant is the most understated because of the subtler contrasts.
I’ve seen the blue and tan version styled pretty snazzily with a patinated cobalt blue suit and a black t-shirt, pants cuffed, with no-show socks.
Crockett & Jones The Princeton Saddle Shoe
Leave it to Crockett & Jones to take an authentic, untouched saddle shoe design, and put it in the body of a high-end Goodyear-welted dress shoe. I wouldn’t call this a dress shoe per se, but it’s certainly built like one. And it screams old American Ivy League.
This shoe is starkly black and white with a touch of broguing on the saddle’s edges. The nubuck leather is exquisitely refined, and the rubber sole is so sharp, you’d think it was leather at first glance.
It’s definitely a throwback aesthetically. However, it’s also modern and upscale in build, featuring an uncommon yet practical composition, kind of like a one-bed-two-bath in Manhattan.
Grenson is a lot like Crockett & Jones, in that it’s a high-end, high-craft shoemaker based in England. Relatedly, the Bellamy is a lot like the Princeton, in that it’s a classic saddle in the body of a high-end shoe.
The Bellamy is a lot more casual though, with a thicker silhouette and more bulbous toe. It isn’t clunky by any means, but it’s just less tapered than the Princeton. Moreover, the red brick sole has a lower and more comfortable heel.
Either way, you’re looking at calfskin leather and Goodyear welting, so these guys are built to last.
Bolano Elwyn Oxford Wingtip
Here’s an undeniably loud shoe for those of you who like bold fashion.
It looks like it came right out of the swing dance clubs of the ‘40s. You never know though; if the zoot suit could make a temporary comeback in the ‘90s, there might be a place for the Bolano Elwyn Oxford Wingtip today.
It has literally all of the details — tons of broguing and a dramatic wingtip. The accents even come in bright blue, bright red, and black.
Still, the slim and sharp taper of the shoe and its black dress-heeled outsole sort of ground the look into a sense of formality. And at ~$80, this budget shoe is well within the easy experimentation price bracket.
Allen Edmonds Shelton
Unfortunately, Allen Edmonds doesn’t currently have a living subline of saddle shoes, but the discontinued Shelton is often easy to find on secondary and grey markets, including Amazon.
The burgundy version of this shoe is a bit legendary because it found a cult following due to the fact it’s designed like a classic saddle shoe, but is incredibly wearable in a range of personal styles thanks to the simple aesthetic and subtle contrast.
Its main contrast comes from the warmth of the burgundy and the starkness of the black. The broguing almost camouflages into the saddle and back. It’s sleek and dressy at first glance, but secretly flashy, for an overall stately look.
It also comes in a less dressy walnut version, which can still be pulled off with a suit. This is Allen Edmonds after all, so the leather is unsurprisingly lush, attractively oiled, and durable.
Paul Smith Sonnet Oxford
Speaking of secretly flashy, you know you can count on Paul Smith to take a traditional prototype and infuse it with some fun and color without taking away from its ability to be worn as it’s meant to be.
The orange accents on the Sonnet Oxford, which live on corners, folds, and just beneath the shoe’s main layer, give it a sort of glow.
It’s subtle, but also not so subtle, since it’s so high contrast. By making the entire shoe black, it tempers this lively addition while also, admittedly, rendering it not a true saddle.
Like a true saddle though, this shoe is classy yet fun, and traditional but not. A true sign of great, innovative design is being able to combine contrary elements in a harmonious, wearable way.
Did I mention this shoe is made in Italy, out of 100% calf leather?
Ambrogio Bespoke Saddle Oxford
Probably the chicest entry on this round-up, this bespoke option from Ambrogio gives the all-American saddle Oxford an Italian make-over.
We’re talking a long sleek taper, a high heel, and a formal and stacked outsole that could easily be on any Italian opera pump. It’s made out of luxurious calfskin leather, hand painted by actual artisans in Spain by the way, and features a calfskin lining as well.
If you’re looking for the Porsche of saddle shoes, look no further. Since this shoe is literally bespoke though, it could take anywhere from a month to two months before you receive your shoes upon ordering.
August Apparel Lincoln Ave Line
The August Apparel Lincoln Ave Line is a treasure trove of different styles of saddle shoes.
The 8086 is the traditional black and white or, in this case, dark navy that’s practically black, while the 5204 is a highly formal patent leather version that can even be worn with a tuxedo. This makes the 5204 one of very few saddle shoes that can be styled that way.
There’s an incredible range here, including nuanced differences like slightly different burnishing and small accent variations.
Moreover, all of the shoes are made of full-grain leather and are Good-year welted. Regardless of which colorway you go for, these are premium shoes.
Here are some frequently asked questions about these classic shoes!
Why were they called saddle shoes?
The decorative panel on the middle of the shoe looks like a saddle on a mount.
What year were saddle shoes popular?
They’ve been in and out of style since they first came out in the early 1900s, but reached their peak in the ‘50s and ‘60s, though people still wear modern, less contrasted versions today.
Are saddle shoes still in style?
They haven’t been “hip” in quite some time, but as an extension of the Oxford dress shoe, they’re pretty classic and probably won’t be completely out of style for a long time.
Meanwhile, Cole Haan is still serving up some practical and modern takes.
Want something loud and costumey? That’s what the Bolano Elwyn is on this list for, and, of course, there are also options on the other side of the spectrum, like Ambrogio and August Apparel’s timelessly elegant dress saddles.
These days there really is a saddle shoe for anyone looking to give them a shot!
Have you ever worn saddle shoes? Let me know in the comment section!