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Our Guide to Vintage Menswear Basics

Vintage style continues to inspire modern men seeking old school sophistication. Certain classic menswear staples maintain timeless and dapper appeal across the decades. In this Vintage Menswear guide, we’ll explore the vintage wardrobe essentials every stylish man should know. From military jackets to Hawaiian shirts, we cover the iconic retro pieces that laid the foundation for today’s menswear. Study this vintage fashion history lesson to build your perfect stash of old school cool.

Military Surplus: Rugged, Functional Style

Surplus military garb provides a treasure trove of utilitarian pieces re-appropriated for everyday vintage flair. These functional designs fuse durability with machismo for a commanding retro look.

The MA-1 bomber jacket emerged in the 1950s for U.S. Air Force and Navy pilots. These slick nylon flight jackets with orange fleece lining and a zippered front became popularised after appearing in iconic films like Top Gun. Team a bomber with jeans, a white tee and sneakers for instant vintage street cred. Stylish variants include the L-2B flight jacket with a fuzzy shearling collar and BR1 model featuring ample patch pockets.

Navy deck jackets and pea coats are wool or wool-blend double-breasted overcoats sporting wide lapels, epaulettes, and engraved anchor buttons. They keep you bundled against brisk weather while saluting maritime roots. Pair pea coats with knits, boots and a newsboy cap for seafaring vintage appeal.

M-65 field jackets in olive cotton canvas became standard issue for U.S. troops during the Vietnam War era. With multiple pockets, hidden hood compartment and a neat pointed collar, they’re a military item evolved into a menswear classic.

The M-1951 fishtail parka was designed for extreme Arctic conditions. The iconic olive drab jacket features a warm fur lined hood and drawstring waist. It became popular with mods and rockers in the 1960s before hitting mainstream popularity still to this day.

Other vintage military jacket styles range from the M-1943 field jacket's loose unlined design to more formal Ike jackets with a fitted waist-cinching belted back. Military coats add rugged utilitarian edge to sharp vintage style.

Rugged Western Wear

Rugged western workwear holds an important place in vintage men’s closets thanks to its durable fabrics, protective leather and outdoorsy rugged machismo.

Cowboy boots are a versatile staple. They range from decorative stitched cowboy boots to sleek Chelsea ranch boots or combo riding boots. Finish the rancher look with denim jeans, pearl snap shirts and bolo ties.

The denim jacket emerged as a workwear basic in the late 1800s. The resilient denim coat with button front and collar became a rebel’s item during the 1950s greaser era. Jean jackets remain an iconic fashion staple and the most coveted are from denim-wear giants like Levis and Lee.

For casual vintage style, pair the classic Western snap shirt with jeans, boots and a cowboy hat for an authentic wild west look. Bandana neck scarves channel cowboys and outlaws. Printed silk neckerchiefs add a pop of colour to basic tee and button-down looks.

Ivy League Preppy Classics

Ivy League style rooted in 1950s East Coast Americana incorporates vintage elements. The polished preppy aesthetic exudes privilege and old money refinement.

The letterman or varsity jacket epitomises this collegiate look. These baseball jackets sport stripes, patches and the wearer's school initials. Letterman jackets migrated from campus to greasers.

Cable knit sweater vests peaked in the 1940s but remain linked to studious Ivy Leaguers. Match one with an Oxford button-down, chinos and loafers. Consider shawl neck or argyle versions too.

Flat front chinos are an Ivy style wardrobe staple, paired with sweater vests, polos and boat shoes. Opt for tan, gray or olive shades. Penny loafers and wingtip Oxfords encapsulate vintage collegiate footwear. These polished lace-ups work from the classroom to the country club.

Dapper Business Essentials

Vintage business attire maintains old school refinement for today's working man, in a sea of bland mass-produced suits, shirts and ties on the modern high street.

The classy fedora and trilby hat styles peaked from the 1920s through 1960s. Center dents and angled brims created dramatic silhouettes. Felt fedoras add retro boldness to modern suits. Vintage options like the Princetown pinch-front boost authentic appeal.

Double-breasted pinstripe suits capture vintage Wall Street style. They taper the waist and broaden shoulders for retro power. Accessorize with a silk pocket square and wingtip Oxfords.

For black tie events, a classic tuxedo or dinner jacket delivers timeless vintage elegance. Shawl or peak satin lapels, self-tie bow, and cummerbund polish the refined aesthetic.

Cap toe Oxfords, spectators and brogued lace-up leather shoes are made for business and formal attire. Decorative perfing and medallions echo dapper retro flair.

Arm garters, tie clips and suspenders complete the dashing vintage business ensemble. Carry a leather briefcase or portfolio case to finish the successful vintage office look.

Laidback Weekend Classics

Vintage style also means relaxed wardrobe basics perfect for weekends and leisure time. Hawaiian or aloha shirts featuring bold tropical prints or geometric Polynesian motifs capture 1950s islander flair. Wear them untucked over chinos or shorts.

Gingham, tattersall and checkered short sleeve button-down shirts deliver a retro picnic ready vibe paired with jeans or shorts. Plain white tees and tank tops also have vintage appeal thanks to iconic brands like Fruit of the Loom and Hanes making them everyday basics.

Timeless Converse Chuck Taylor All Star sneakers first emerged in the 1920s and remain forever cool. Jack Purcell and Keds sneakers also offer vintage Americana charm.

V-neck sweaters make for cozy vintage style. Pair a v-neck cardigan, sweater vest or pullover with a collared shirt for easy vintage attitude.

Essential Finishing Touches

Vintage details like accessories make any man's outfit stand out with old school refinement.

Pocket squares lend colour and retro elegance to a blazer. Fold them in classic shapes like wings, puffs or peaks. Patterned ties like paisley, plaid, striped or Art Deco prints reference the past. So do engraved bolo ties and vintage silk bow ties.

Seasonal hats like straw Panama hats or driving caps top off casual vintage summer style. Try a wool flat cap or bowler for winter timeless flair.

Leather gloves, suspenders, arm garters and tie pins deliver sophisticated vintage polish. Clubmaster sunglasses and classic aviators channel mid-century cool. Vintage wristwatches also complete the throwback look. Consider concert watches, LED digital watches, chronographs or pocket watches on a chain.

Cultivate Your Vintage Style

Today’s menswear still derives inspiration from classic vintage silhouettes, fabrics and details. By studying iconic retro pieces from military might to Ivy League prep, gents can curate refined vintage flair. Once you discover your personal blend of laidback classics, rugged military and refined retro businesswear, your unique vintage style will confidently shine through.

You can shop for a whole host of mens vintage clothing and vintage accessories for men 24/7 at and of course if you ever need a little advice or a helping hand just drop us a line or get us on live chat.

Until nect time

Emma x

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