Men in the 1950s dressed with purpose. Every outfit told a story \u2013 the rebellious greaser, the clean-cut preppy, the hardworking blue-collar guy. You could tell who a man was by what he wore. Today, you can borrow those same looks and make them work for your life. Here is exactly how guys dressed in the 50s and how you can wear those styles now.<\/p>\n
The most iconic 50s style belongs to the greaser. Think Marlon Brando in The Wild One<\/em>. The centerpiece was a black leather jacket \u2013 usually a double-rider style made from cowhide or horsehide. Underneath, a plain white crew-neck T-shirt, nothing fancy. Jeans were raw denim, straight-leg, and often cuffed at the bottom. Boots or simple lace-up boots like the classic engineer boot finished the look.<\/p>\n If you want this vibe today, focus on fit. The jacket should hit at the waist, not hang low. Your T-shirt should be snug but not tight. The jeans need a straight or slim-straight cut \u2013 no skinny or baggy. Stick with raw or dark wash denim. For boots, look for plain leather work boots or engineer boots from brands like Red Wing or Chippewa. A simple razor comb through your hair with a touch of pomade ties it all together.<\/p>\n Not every guy in the 50s was a greaser. The preppy look ruled campuses and offices. Guys wore button-down Oxford cloth shirts with the collar unbuttoned \u2013 the original “OCBD.” Chinos in khaki or olive, often with a sharp crease down the front. V-neck sweaters, cardigans, and blazers over the shirt. Penny loafers were the go-to shoe, often in brown cordovan leather.<\/p>\n You can recreate this easily. Start with an oxford shirt in a light blue or white. Roll the sleeves once or twice. Pair it with khaki chinos that fit straight through the leg, not too slim. Add a navy blazer if you want dressier, or a merino wool sweater if casual. For shoes, get real penny loafers \u2013 look for leather soles and a good brand like Bass Weejuns. A thin leather belt matching your shoes finishes the outfit. This look works for a date, casual office, or Sunday brunch.<\/p>\n Many working men in the 50s wore denim as work clothes, not fashion. Canvas chore coats, denim jackets, and heavy cotton duck pants were common. Flannel shirts in plaid patterns were layered under jackets. Boots were sturdy and scuffed \u2013 they were tools, not accessories. The key was function: everything had a job to do.<\/p>\n To wear this today, choose quality over trend. A Carhartt or Pointer Brand chore coat in brown duck canvas is perfect. Under it, wear a wool flannel shirt in red-and-black or green-and-black plaid. Pair with raw denim jeans or harder-wearing cotton twill pants. For boots, think lace-up work boots like the Red Wing Iron Ranger or Thorogood Moc Toe. Avoid distressed or pre-worn finishes \u2013 real workwear shows its history naturally. If you work with your hands, this style fits your life already.<\/p>\n Suits in the 50s had a distinct shape. Jackets were longer, covering the seat. Lapels were wide \u2013 around 3 to 3.5 inches. Trousers were high-waisted and often pleated, with a full leg that tapered slightly to the ankle. Two-button jackets were standard, with natural shoulders (no heavy padding). Men wore fedoras or homburgs outdoors. Ties were skinny or medium width, often with bold patterns.<\/p>\n You can get this look without looking like a costume. Find a vintage-inspired suit from brands like Suitsupply or Spier & Mackay. Look for a jacket that sits longer, with wide notched lapels. Trousers should sit at your natural waist \u2013 that means they\u2019ll be higher than modern low-rise pants. Wear a thin tie in a paisley or geometric pattern. If you want a hat, go with a fedora in grey or brown felt. Just remember: remove the hat indoors. That\u2019s a rule from the 50s that still shows respect today.<\/p>\n Shoes in the 50s were leather or canvas, and they were built to last. The most common men\u2019s shoes were oxfords, loafers, and boots. Dress shoes were plain-toe or cap-toe oxfords in brown or black. Casual shoes included saddle oxfords (two-tone white and black or brown) and canvas sneakers like Converse All Stars. Work boots were heavy leather with thick rubber soles.<\/p>\n Care makes these shoes last. For leather oxfords, use a horsehair brush after each wear, then apply neutral or color-matched wax polish weekly. Saddle soap cleans leather boots without drying them out. For canvas sneakers, scrub with a mild soap and water, then air dry. Never machine wash. A suede brush lifts dirt from suede loafers without damaging the nap. If you treat your shoes right, they will serve you for years \u2013 just like a 50s guy expected.<\/p>\n Hair in the 50s was styled with grease or pomade \u2013 hence the name “greaser.” Guys wore pompadours, flattops, and side parts. The hair was slicked back or swept up with volume at the front. Parting was sharp. Facial hair was rare; most men were clean-shaven or had a thin mustache.<\/p>\n If you want a 50s-inspired hairstyle today, you need the right product. Oil-based pomade from brands like Murray\u2019s or Suavecito gives that high-shine, all-day hold. For a pompadour, blow-dry your hair up and back, then apply pomade and comb into shape. A flattop requires a barber who knows how to cut that precise flat crown. For grooming, keep facial hair trimmed very short or go clean. A classic safety razor gives a closer, cleaner shave than modern multi-blade cartridges \u2013 and it costs less per shave.<\/p>\n Levi\u2019s 501 original button-fly jeans were the most common. They had a straight leg, high waist, and were made of stiff raw denim. No stretch, no pre-distressing. Guys wore them cuffed at the bottom, often with a belt. If you buy a pair today, get raw or rigid denim and expect some break-in time.<\/p>\n Yes, but only for sports or casual wear. Converse All Stars (high-tops) were popular, usually in black or white. Keds also made low-top canvas sneakers. They were not worn with suits or nice clothes. Sneakers were for playing basketball, hanging out, or doing yard work \u2014 never for a date or job interview.<\/p>\n Short sleeve button-up shirts in patterns like Hawaiian or bowling prints were common. Lightweight cotton chinos or seersucker pants kept them cool. Espadrilles or canvas boat shoes were worn without socks. Many guys also wore short-sleeved polo shirts with the collar popped up \u2014 just like the golf look.<\/p>\n Yes, but you have to commit to the rest of the outfit. Wear a fedora with a tailored blazer, dark jeans or trousers, and leather shoes. Avoid wearing it with a hoodie or shorts. Choose a neutral color like charcoal or taupe. Take it off when you go indoors. If you feel awkward, skip it \u2014 but plenty of guys pull this off well.<\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":" Men in the 1950s dressed with purpose. Every outfit told a story \u2013 the rebellious greaser, the clean-cut preppy, the hardworking blue-collar guy. You could…<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":"","rank_math_focus_keyword":"how did guys dress in","rank_math_description":"How did guys dress in the 50s? Get the real greaser, preppy, and workwear looks. Leather jackets, fedoras, denim, and shoes.","rank_math_title":"How Did Guys Dress in the 50s","rank_math_seo_score":""},"categories":[16],"tags":[],"class_list":["post-65","post","type-post","status-publish","format-standard","hentry","category-clothing-outfits"],"_links":{"self":[{"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/posts\/65","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/comments?post=65"}],"version-history":[{"count":0,"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/posts\/65\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/media?parent=65"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/categories?post=65"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.yawteef.com\/blog\/wp-json\/wp\/v2\/tags?post=65"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}The Ivy League Prep: Clean, Sharp, and Timeless<\/h2>\n
The Workwear Look: Durable, Honest, and Practical<\/h2>\n
Suits and Formal Wear: Structure and Drape<\/h2>\n
Footwear Choices: What Guys Wore on Their Feet<\/h2>\n
Hair and Grooming: The Finishing Touch<\/h2>\n
Frequently Asked Questions<\/h2>\n
What kind of jeans did guys wear in the 50s?<\/h3>\n
Did guys in the 50s wear sneakers?<\/h3>\n
How did guys in the 50s dress for summer?<\/h3>\n
Can I wear a fedora today and not look like a costume?<\/h3>\n