Men's Vintage Shirts

Embrace timeless style with our collection of men's vintage shirts, where classic designs meet modern comfort. Each shirt in this selection is crafted to offer a nod to the past while ensuring you stay comfortable and confident in every setting. Whether you're heading out for a casual day with friends or looking to add a touch of nostalgia to your wardrobe, these shirts are versatile enough to suit any occasion. Explore an array of colors and patterns that capture the essence of vintage charm, all while enjoying the quality and lasting value L.L.Bean is known for.

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476 Items

Men's Bean's Vintage Soft Rugby, Mockneck
Price was from: $79 now: $54.99

A vintage-inspired rugby shirt in dusty olive, featuring a mockneck and crafted from 100% jersey-knit cotton.
Men's Bean's Vintage Soft Knit Henley

A versatile, all-season henley in classic navy heather with a unique honeycomb waffle-knit texture.
Men's Bean's Vintage Soft Rugby, Chest Stripe

A vintage-inspired rugby shirt in blue, crafted from 100% cotton for ultimate softness and comfort.
Men's Scotch Plaid Flannel Shirt, Traditional Fit
Price was from: $59.95 now: $49.99

A soft, durable flannel shirt in authentic Scottish tartans, made from high-quality Portuguese cotton.

Pros: Fits well Good quality Softness Warmth Comfortable
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $59.99

A slim-fitting, 100% cotton flannel shirt in faded black plaid, offering vintage softness and comfort.

Pros: Beautiful design High quality Warmth Soft fabric Comfortable fit
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $44.99

A vintage indigo, wrinkle-free, ultrasoft brushed cotton shirt with a slightly fitted untucked fit.

Pros: Great fit Attractive appearance Wrinkle-free Comfortable brushed cotton Nice color
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit

A slim-fit indigo heather shirt made from 100% cotton flannel, brushed and garment-washed for softness.

Pros: Perfect fit Comfort Softness Warmth Durability
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid

A rugged midweight flannel shirt in vintage indigo plaid, 100% cotton, with a slightly fitted untucked fit.

Pros: Great fit High-quality material Well-built Very comfortable Excellent return policy
Men's Signature Microwale Corduroy Shirt
Price was from: $89 now: $43.99

A cozy, classic mariner blue shirt made from 100% cotton microwale corduroy in a streamlined Slim Fit.
Men's Bean's Vintage Soft Rugby, Mockneck, Chest Stripe
Price was from: $79.95 now: $39.99

A jersey-knit cotton rugby shirt with a mockneck, bold stripes, and rubberized buttons for extra softness.
Men's Bean's Vintage Soft Rugby, Stripe
Price was from: $69.95 now: $49.99

A jersey-knit cotton rugby shirt with rubberized buttons, twill collar, and garment-washed softness.
Men's Sunwashed Corduroy Shirt, Slightly Fitted Untucked Fit, Plaid

A lightweight red corduroy shirt with a vintage plaid look, washed for softness and all-season comfort.
Men's Stonecoast Hemp Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Print

A blue short-sleeve shirt in a hemp/cotton blend, offering breathable comfort and vintage-inspired patterns.
Men's Stonecoast Hemp Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
Price was from: $64.95 now: $54.99

A breathable tan short-sleeve shirt crafted from a soft, durable hemp-cotton blend with vintage-inspired patterns.
Men's Signature Washed Field Shirt, Slim Fit

A rugged brown herringbone cotton shirt with a slim fit and vintage-inspired details.
Men's Stonecoast Hemp Shirt, Long-Sleeve, Slightly Fitted Untucked Fit

A blue hemp/cotton blend shirt offering breathable comfort, durability, and a slightly fitted untucked style.
Men's Stonecoast Hemp Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Stripe

A rugged, breathable gray shirt with a soft hemp/cotton blend and vintage-inspired stripes.
Men's Signature Northwoods Twill Shirt

A rugged deep blue cotton flannel shirt with a herringbone texture and slim fit for year-round wear.
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth

A charcoal heather flannel shirt with sheepskin shearling lining, offering superior softness and traditional fit.

Pros: Beautiful design Roomy fit Warmth Durable Superior softness
Men's Chamois Shirt, Traditional Fit, Plaid
Price was from: $84.95 now: $69.99

A heavy-weight, ultra-soft plaid flannel shirt in barley, made from 7.5 oz. Portuguese cotton.

Pros: High quality Attractive design Softness Warmth Comfortable fit
Men's Chamois Shirt, Traditional Fit

A deep green, heavy-weight Portuguese cotton flannel shirt, perfect as a shirt, light jacket, or essential layer.

Pros: Nice colors Great quality Warmth Versatile use Comfortable fit
Men's Two-Layer River Driver's Shirt®, Traditional Fit Henley

A vintage indigo heather Henley with a wool blend outer layer and soft cotton inner layer.

Pros: Quality construction Perfect fit Warmth Comfortable Versatility
Men's Sunwashed Canvas Shirt, Traditional Fit

A cadet blue, 100% cotton canvas shirt with a relaxed fit and durable double-needle stitching.

Pros: High quality Durable Comfortable Good fit Nice color
Men's Premium Double L® Polo, Long-Sleeve Without Pocket

A vintage indigo, long-sleeve polo made from supersoft cotton pique-knit that resists wrinkles, fading, and shrinking.

Pros: High quality Durable Good fit Comfortable Great color options

Men's Vintage Shirts

There’s something truly special about the timeless appeal of men’s vintage shirts—each one carries a sense of character and history that modern styles often strive to capture. Whether you’re drawn to the classic patterns, the sturdy feel of well-woven cotton, or the easy comfort that comes from a shirt that’s been thoughtfully made, these pieces offer a unique way to express personal style while enjoying lasting quality. Vintage-inspired shirts are known for their versatility; they transition seamlessly from casual afternoons spent around a backyard fire pit to relaxed evenings spent with friends at a local diner. The details—like distinctive buttons, heritage prints, and relaxed collars—add a touch of nostalgia that never feels out of place. For many, slipping on a vintage-style shirt is like stepping into a favorite memory: a chilly December morning spent walking the dog, or a holiday gathering where comfort and warmth matter just as much as looking put-together. These shirts aren’t just for collectors or those with a love of retro style; they’re for anyone who appreciates clothing that’s durable, comfortable, and always ready for the next adventure.

When considering a men’s vintage shirt, it’s worth thinking about how it fits into your daily life—or the life of someone you care about. These shirts make thoughtful gifts for dads, brothers, or friends who appreciate a blend of practicality and timeless style. They’re a great choice for anyone who values clothing that stands up to frequent wear, whether it’s layered under a favorite sweater for a winter walk or worn solo during the first mild days of spring. The ll bean vintage shirt, for example, is a reminder of how classic design and modern comfort can come together in a way that feels both familiar and new. The right vintage shirt offers more than just good looks; it’s a reliable companion for everything from weekend projects in the garage to exploring a local trail. With their easy-to-care-for fabrics and enduring construction, these shirts are built to last—making them a smart investment for anyone who prefers clothing with staying power. And with so many patterns and colors to choose from, it’s easy to find a shirt that fits your own sense of style or makes the perfect gift for someone special.

If you’re looking to expand your wardrobe with shirts that offer both classic appeal and everyday comfort, you’ll find plenty of inspiration among our selection. Vintage shirts are all about quality, versatility, and the little details that set them apart. They remind us that great style never goes out of season, and that the right shirt can make every day feel a little more memorable. For even more options, including modern takes on classic favorites, visit our curated collection of Mens Fashionable Shirts. Whether you’re shopping for yourself or searching for a gift that’s sure to be appreciated, you’ll find shirts designed to keep up with every adventure—season after season.

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Men's Vintage Shirts