1950s Mens Shoes

1950′s Mens shoes include Saddle shoes, two toned oxfords, Chukka boots, Winkelpickers, Chelsea boots, Loafers, Creepers, Nubuck oxfords, and more. These vintage style modern shoes are great choices for your 1950′s inspired wardrobe.

Learn about mens 1950′s Shoes before you shop.

1950's White Nubuck Shoes

1950's White Nubuck Shoes

$47.99

The Exeter' from Bass is a timeless oxford that will never go out of style. ; Leather, nubuck and suede uppers offer a great look that will last for years. ; Contrast stitc... [Read more]

Store: 6pm

Cole Haan - 1950's Style Air Monroe Penny Loafers

Cole Haan - 1950's Style Air Monroe Penny Loafers

$159.99

Cole Haan Air Monroe Penny loafers. ; Classic 1950's mens shoe silhouette. [Read more]

Store: Zappos.com

Cole Haan - Air Carter Oxfords

Cole Haan - Air Carter Oxfords

$178.00

These polished cap toe 1950's Style oxford shoes are perfect for semi and formal attire. [Read more]

Store: Zappos.com

1950's Men White Nubuck Shoes

1950's Men White Nubuck Shoes

$110.45

Nothing says 1950's casual comfort like white nubuck shoes. [Read more]

Store: Shoebuy.com

1950's Stacy Adams Men's Madison Cap Toe Woven Oxford

1950's Stacy Adams Men's Madison Cap Toe Woven Oxford

$125.00

A cross between an Oxford and a saddle shoes makes this a 1950's dream come true. [Read more]

Store: Endless.com

1950's Stacy Adams Men's Madison Cap Toe Oxford Shoes

1950's Stacy Adams Men's Madison Cap Toe Oxford Shoes

$89.95

Bring classic style to work attire with the Madison shoe from Stacy Adams. [Read more]

Store: Endless.com

Area Forte Men's 1950 Shoe

Area Forte Men's 1950 Shoe

$287.95

1950s mod, single strap, shoes similar to the winkelpicker shoes. [Read more]

Store: Endless.com

50's Chukka Shoes- Camel Suede

50's Chukka Shoes- Camel Suede

$129.95

Classic 1950's youth style designed with modern comfort features, in supple, color-rich suede. Highly cushioned memory-foam insole for extreme comfort. [Read more]

Store: Shoebuy.com

Clarks Men's Desert Boot

Clarks Men's Desert Boot

$99.99

An international cult classic, the Desert Boot is inspired by the crepe-soled boots worn by British officers in World War II. Its soft, supple leather upper and a genuine p... [Read more]

Store: Endless.com

1950's Vintage Men's Chukka Oxford Boot

1950's Vintage Men's Chukka Oxford Boot

$209.50

It's totally vintage-inspired with its classic silhouette, distressed suede upper, and wooden stacked sole. [Read more]

Store: Endless.com

1950s Men's Manny Chukka Boot

1950s Men's Manny Chukka Boot

$247.95

It's totally vintage-inspired with its classic silhouette, distressed suede upper, and wooden stacked sole. [Read more]

Store: Endless.com

Clarks Originals 1950s Men's Desert Boot

Clarks Originals 1950s Men's Desert Boot

$95.99

An international cult classic, the Desert Boot was inspired by the crepe-soled boots worn by British officers in World War II. Soft, supple suede full grain leather uppers ... [Read more]

Store: Endless.com

Rydell Mens Leather Plain Toe Slip-on Lace-up

Rydell Mens Leather Plain Toe Slip-on Lace-up

$40.00

1950s high style - Bicycle toe slip on shoe. You can not help but be noticed in these shoes. [Read more]

Store: Stacy Adams

Bass Men's Burlington 1950s mens Saddle Shoe

Bass Men's Burlington 1950s mens Saddle Shoe

$88.95

A classic 1950s mens saddle shoe. This is a great quality shoe for men and a perfect fit for that classic 50's look. [Read more]

Store: Endless.com

Stacy Adams Men's Madison Boot

Stacy Adams Men's Madison Boot

$95.00

Nab this boot from Stacy Adams and give your wardrobe an instant dose of dapper appeal. The classic design features a round toe, lizard embossing, and full lacing for an ad... [Read more]

Store: Endless.com

1950's Men's Runnell Chukka Boot

1950's Men's Runnell Chukka Boot

$104.99

For superior style that delivers big comfort, nothing beats Johnston & Murphy's Runnell boot. Expertly crafted from water-resistant leather, this shoe features memory-f... [Read more]

Store: Endless.com

1950's Creeper Style Shoes

1950's Creeper Style Shoes

$74.95

The platform maintains the classic Creeper style and a very smooth stride. [Read more]

Store: Endless.com

rockabilly Creeper Shoes

rockabilly Creeper Shoes

$63.25

A fun, classic 1950's creeper shoe for any retro wardrobe. [Read more]

Store: Endless.com

Black Faux Suede 1950's Creeper Shoes

Black Faux Suede 1950's Creeper Shoes

$79.95

Hip platform sneakers featuring a suede upper, mid platform and checkered toes. [Read more]

Store: Shoebuy.com

Demonia Creeper White Leather

Demonia Creeper White Leather

$99.95

Contemporary platform sneakers featuring a leather upper with checkered toes. Available Colors: Black Leather, White Leather. [Read more]

Store: Shoebuy.com

Demonia Creeper Shoes Black/White Leather

Demonia Creeper Shoes Black/White Leather

$109.95

Contemporary platform sneakers featuring a leather upper with a wingtip toe. [Read more]

Store: Shoebuy.com

1950s' Loafer- Georgetown Shoe by Allen Edmonds

1950s' Loafer- Georgetown Shoe by Allen Edmonds

$199.00

Classic penny loafer in high quality soft European calfskin leather. [Read more]

Store: Jos. A. Bank

Mens Saddle Shoes Jos. A. Bank

Mens Saddle Shoes Jos. A. Bank

$145.00

Five-eyelet balmoral saddle oxford. Full leather lining. Memory Foam insole provides shock absorption and cushioning. Security-friendly fiberglass shank. Rubber outsole for... [Read more]

Store: Jos. A. Bank

1950's Classic Buck Shoe by Jos. A. Bank

1950's Classic Buck Shoe by Jos. A. Bank

$145.00

Classic 1950s' Nubuck Shoes- Four-eyelet, plain toe buck shoes with rubber outsoles. Leather-lined comfort system inside. [Read more]

Store: Jos. A. Bank

1950's Style Penny Loafer Shoes

1950's Style Penny Loafer Shoes

$129.99

Hand-sewn Italian leather upper. Leather/rubber sole and heel. [Read more]

Store: Jos. A. Bank

1950's Men's Berkley Penny Loafer Shoes

1950's Men's Berkley Penny Loafer Shoes

$77.90

Simply the standard, Florsheima€™s Berkley penny loafer is a must-have part of your footwear collection. Paired with workday suiting or alongside khakis, no ... [Read more]

Store: Endless.com

1950's  Men's Bainbridge Penny Loafer

1950's Men's Bainbridge Penny Loafer

$52.66

A pebbled leather upper adds texture and casual appeal to this smart-looking penny loafer from Sperry Top-Sider. An easy match for your office khakis, the Bainbridge featur... [Read more]

Store: Endless.com

Stacy Adams Men's Lionel 1950's Loafer with Monk Strap

Stacy Adams Men's Lionel 1950's Loafer with Monk Strap

$74.95

There's something both old-world classy and urban cool about this loafer.A mix of 50's Winkelpicker and loafer. [Read more]

Store: Endless.com

Men's Loafer- Classic Simple 50's Style

Men's Loafer- Classic Simple 50's Style

$99.95

Rockport has always been one step ahead of the times, believing the perfect shoe has not yet been invented. This positive dissatisfaction compels them to constantly improve... [Read more]

Store: Endless.com

Sperry Top-Sider Men's Authentic Original 2-Eye Boat Shoe

Sperry Top-Sider Men's Authentic Original 2-Eye Boat Shoe

$36.44

The original design that launched Sperry Top-Sider, this two-eyelet moccasin remains the benchmark for boating shoes. From the 360A° lacing system with rust-proof e... [Read more]

Store: Endless.com

Hush Puppies Men's Pacino Saddle Shoes

Hush Puppies Men's Pacino Saddle Shoes

$67.99

Vintage brands make the best vintage shoes. Love these black and brown saddle shoes. [Read more]

Store: Endless.com

Men's Boston Saddle Oxford Shoes

Men's Boston Saddle Oxford Shoes

$200.00

Once you slip into the saddle, you're in charge. High end fit and comfort are to be expected. [Read more]

Store: Endless.com

Johnston & Murphy Men's Runnell Chukka Boot - Mens Camel Suede Shoes

Johnston & Murphy Men's Runnell Chukka Boot - Mens Camel Suede Shoes

$104.99

For superior style that delivers big comfort, nothing beats Johnston & Murphy's Runnell boot. Expertly crafted from water-resistant leather, this shoe features memory-f... [Read more]

Store: Endless.com

1950's Mens Chukka Boots

1950's Mens Chukka Boots

$228.00

A simple yet sophisticated silhouette in soft leather. Stitch out constuction. Leather sole with rubber forepart. 100% Leather uppers. Imported. [Read more]

Store: Jos. A. Bank

Florsheim Men's Elwood Monk Strap Loafer - Mens Shoes

Florsheim Men's Elwood Monk Strap Loafer - Mens Shoes

$159.95

Exude confident, GQ style by pairing the Florsheim Elwood loafer with tailored business ensembles. A smooth leather or suede upper creates a sophisticated and polished silh... [Read more]

Store: Endless.com

John Blair Saddle Shoes

John Blair Saddle Shoes

$49.99

Decidedly retro, these two-tone classics deliver long-lasting cushioning and durability. Leather with a flexible TPR outsole and comfortable manmade lining. Import. Widths:... [Read more]

Store: Blair.com

Cole Haan Men's Air Colton Eva Saddle Oxford - Mens Shoes

Cole Haan Men's Air Colton Eva Saddle Oxford - Mens Shoes

$108.90

Look smart from every angle when you don the Air Colton saddle shoe from Cole Haan. A hued outsole and contrast tongue and heel trim give this classic shoe a decidedly mode... [Read more]

Store: Endless.com

David Spencer Men's Saddle Oxford - Mens Shoes

David Spencer Men's Saddle Oxford - Mens Shoes

$134.95

Dress up your casual look with this handsome balmoral saddle oxford from David Spencer. It features a contrasting leather upper with classic broguing and a full leather lin... [Read more]

Store: Endless.com

Florsheim Men's Valco Saddle Lace-Up - Mens Shoes

Florsheim Men's Valco Saddle Lace-Up - Mens Shoes

$110.00

Not Applicable [Read more]

Store: Endless.com

Johnston & Murphy Men's Brennan Saddle Oxford - Mens Shoes

Johnston & Murphy Men's Brennan Saddle Oxford - Mens Shoes

$134.95

Throughout time, many things change. A few, however, never do. Work doesna€™t look like it used to. Suits arena€™t necessarily the uniform, an... [Read more]

Store: Endless.com

Neil M Men's Gentry Saddle Oxford - Mens Shoes

Neil M Men's Gentry Saddle Oxford - Mens Shoes

$200.00

The men's Gentry saddle oxford from Neil M. is produced to give you incredible comfort all day, on all surfaces, for all occasions. It features a leather covered polyuretha... [Read more]

Store: Endless.com

Dr. Martens Rafi Saddle Shoe - White/Black Smooth

Dr. Martens Rafi Saddle Shoe - White/Black Smooth

$109.95

A refinement of Dr. Martens classic upper design, the Saddle Shoe is a badge of subcultural identity and hints at several strands of youth culture. The striking color combi... [Read more]

Store: Shoebuy.com

Vintage Shoe Company - Harding Saddle Oxford (Black Vintage) - Footwear

Vintage Shoe Company - Harding Saddle Oxford (Black Vintage) - Footwear

$192.99

Zappos.com is proud to offer the Vintage Shoe Company - Harding Saddle Oxford (Black Vintage) - Footwear: All Vintage Shoe Company products are individually crafted by hand... [Read more]

Store: Zappos.com

Rock & Republic Men's Gaetan Double Monk Strap - Mens Shoes

Rock & Republic Men's Gaetan Double Monk Strap - Mens Shoes

$162.50

Get harness boot styling in a dress shoe with this Gaetan monk strap from Rock & Republic. The supple calfskin upper is smooth, with traditional slim laces and a padded... [Read more]

Store: Endless.com

Italian Leather Monk Strap Shoes

Italian Leather Monk Strap Shoes

$70.00

The classic monk shoe, a perfect fit for any season. [Read more]

Store: Paul Fredrick MenStyle

Vintage Shoe Company Judson 5-Eye Oxford (Men's) - Black Harness

Vintage Shoe Company Judson 5-Eye Oxford (Men's) - Black Harness

$214.95

The traditional oxford appeared in the mid 19th-century in Scotland where it was a fashionable dress shoe with a handsome, unadorned silhouette. Our Judson is constructed w... [Read more]

Store: Shoebuy.com

Vintage Shoe Company Harding (Men's) - Brown Vintage

Vintage Shoe Company Harding (Men's) - Brown Vintage

$274.95

With origins linked to the beginning of the 20th century, the saddle shoe emerged as the quintessential style of the 1950s, when the immensely popular oxford design was a f... [Read more]

Store: Shoebuy.com

Vintage Shoe Company Bluff (Men's) - Brown Vintage

Vintage Shoe Company Bluff (Men's) - Brown Vintage

$298.95

Worn primarily by polo players in the 1800s, the chukka boot quickly thereafter became a menswear classic. Handcrafted from either a soft, supple leather or worn, textured ... [Read more]

Store: Shoebuy.com

Bass - Elden (Natural Vintage Burnished Canvas)

Bass - Elden (Natural Vintage Burnished Canvas)

$49.99

6pm. com is proud to offer the Bass - Elden (Natural Vintage Burnished Canvas) - Footwear: This season, Bass® brings to you the latest in saddle shoe trends with the El... [Read more]

Store: 6pm

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