Like most men, I hate shopping and I don’t care much enough to follow fashion. Up until recently, I lived comfortably in T shirts and cargo shorts — and the only reason that changed was because I got a job that expected more from me. Even still, I like being comfortable and didn’t want to spend thousands of dollars on clothes every year to keep myself looking “smart.” So instead of getting lost in a mall, I went with a retro capsule wardrobe.
Men’s vintage inspired clothes are comfortable, versatile, and can help you look put together without ever going obsolete. Because of that, I’ve decided to write up a guide on how to create a men’s vintage style wardrobe. Due to its pervasiveness, versatility, and comfort, I’ll be placing a focus on men’s vintage casual clothing and men’s vintage workwear.
The Basics: Planning a Capsule Wardrobe for Men
A capsule wardrobe is a planned out and versatile set of clothes that covers all you will need in day to day life. While traditionally it was used to encompass an entire wardrobe, many people create capsule wardrobes for things like car show costumes, work, travel, vacations, or for events.
Its appeal primarily comes from what it involves: capsule wardrobes are thought out, manageable, and controlled. You don’t own what you don’t wear, you don’t buy what you don’t need, and everything you own sees enough use to justify being kept. In the long run this saves you lots of money and time.
When planning a casual capsule wardrobe, begin with an outline. Think about what you enjoy wearing, how often you get to wear it, and what impression you want to give. Also consider your climate, activity level, preferred style and what’s comfortable.
What you have in your capsule wardrobe depends entirely on you (and your laundry schedule), but this was the point I started from:
- 3-5 Shirts ( e.g. Casual Button Up / Dressier Button Up / T-shirt / Overshirt )
- 3 Pants ( e.g. Jeans / Chinos / Slacks / Shorts )
- 1-2 Outerwear ( e.g. Leather Jacket / Denim Jacket / Cardigan )
- 2 Shoes ( e.g. Brown / Black / Dress / Sneakers )
- Misc ( e.g. Black Belt / Brown Belt / Sunglasses / Neckwear / Vest / Suspenders / … )
… for a total of about 12-15 articles of clothing, meant to be worn during a five day week.
My Example
I wrote my first vintage capsule wardrobe outline in 2018, aiming for something that was rugged, durable, and middle-of-the-century (’40s-’60s):
Early Capsule Wardrobe outline dug out from a tattered notebook.
With some adaptation over the years, here’s what I ended up with:
Another Capsule Wardrobe Example
A pair of brown lace-up boots, a 1920s workwear cap, and a pair of suspenders would give this wardrobe a 1920s-1930s flair.
Finding Men’s Vintage Inspired Casual Clothes
Below are tips, considerations, and suggestions by clothing type. It will include vintage men’s clothes as well as some recommended men’s vintage inspired brands for every budget.
Shirts
Solid colors, light colors, and plaid are all the most versatile patterns for shirts. Similarly, long sleeved collared shirts generally hold up longer and look more “classic” than short sleeved collared shirts. Make sure the silhouette is looser or order a size up.
My recommendations:
- Semi-formal/dressier shirt, lightly patterned
- Plaid or check workshirt, sized up (works as a good shirt-jacket too)
- Solid, textured olive or muted green button-up
- Chambray/washed denim shirt
- T-shirts (white, cream, neutral color solid — worn slim fitting)
JC Penney Shirts (VINTAGE) – 1950s JC Penney Ranchcraft/casual shirts are a good (and comfortable) shirt.
Lucky Brand ($$) – Wait for sales when their shirts drop to around $30. Good classic work shirts in both slim and wide cuts. Avoid their T-Shirts as they do not last.
L.L.Bean ($$) – Varied solid and patterned button up shirts. Check product reviews.
Eddie Bauer ($) – Runs sales often that bring their shirts down to >$30 apiece. Runs slim – order one size up
Duluth Trading Co ($$) – Thick outdoorsman’s plaids and henley tees with a great product guarantee.
Dixxon Flannels ($$) – Solid USA made flannels.
River Junction ($$) – Loose, comfortable, Old West style shirting.
Runabout Goods ($$$) – Excellent no-frills hiking and outdoors shirts.
Bryceland’s ($$$) – Plaid and Western style with a more modern/slim silhouette.
Mister Freedom ($$$) – Themes ranging from military surplus to sailor wear to gentleman’s shirting.
Standard and Strange ($$$) – Retailer for various brands. Milsurp, sportsman, outdoorsman, and other rugged workwear types.
Simon James Cathcart (UK – $$) – 1910s-1930s style shirts, very vintage looking.
Clutch Cafe (UK – $$$) – Retailer for various brands. Excellent plaids and Hawaiian shirts.
Target ($) – For the budget shopper, Target often has good basic shirts.
Kai D Utility For the urban rustic. made in New York City.
Buck Mason – Classic American style T shirts, jacket, sweatshirts. Trendy looks for a slightly rugged style.
Cathcart London (UK) – 1920s -1940s suits, trousers, shirts, knickerbocker suits, vests, coats, jackets, knitwear both dress and casual.
More Workwear Shirts – A mix of brands and styles for all budgets. Both USA and UK sites.
Denim on denim workwear
Knit Sweaters and Cardigans
I don’t recommend having more than one or two knits unless you are in a very cold climate. Thicker knits will always look more vintage and rugged, but finer knits will work for the ’60s-’70s.
My recommendations:
- Olive army issue sweaters always have a rugged, vintage feel. The WWII style High Neck Sweater is especially iconic.
- Grey, navy, or muted color shawl sweater (for 1910s-1940s)
- Solid, dark color or off-white turtleneck (for 1940s-1960s)
BeechwoodandBriars (VINTAGE) – Affordable vintage sweaters of various styles.
Dehen 1920 ($$$) – Heritage cut, high quality wool sweaters.
Clutch Cafe (UK – $$$) – Thick-knit Fair Isles, Shawl Sweaters, and other vintage styles including knit short sleeve shirts.
Revival Vintage (UK – VINTAGE) – Vintage long sleeve and short sleeve knitwear.
Oldfield Clothing – Reproduction knitwear and clothing from the 1920s/30s/40s
Military Surplus Stores – Available online and in person, these usually sell durable and timeless knits. Here’s a good variety.
1960 Workwear- western pants, shirts and blue jeans
Pants and Jeans
Good pants are stiff. That quality matters a lot when it comes to something that will last. Avoid pants that are stretchy or advertise being flexible, and stick to something that is either wide-legged or a straight taper. Keep to a medium-high waist too.
My recommendations:
- WWII issue wool trousers
- Canvas trousers
- Jeans (straight leg, medium-high waist) in a dark wash
- Chinos or corduroy pants in khaki/brown
Prison Blues / Amazon shop ($) – Rugged, raw work jeans.
Bronson Mfg / MAYA ($$) – Unique military reproduction and 1940s-1950s style jeans and trousers.
Red Tornado (Ebay) – Vintage workwear jeans, jackets, shirts
Mister Freedom ($$$) – Mid-to high rise, slim and straight leg, vintage inspired pants with vintage or heritage fabrics.
The Real McCoy’s (UK – $$$) – WWII style wide leg, loose fitting trousers.
Standard and Strange ($$$) – Vintage style pants as well as some contemporary fits with classic details
Collectif (UK) – Men’s 1940s and 1950s denim jean, knit shirts, and light jackets.
Iron Heart ($$$) – Renowned for very heavy, thick motorcycle denim jeans in a variety of classic-style cuts.
Eat Dust (UK – $$$) – Vintage military-style cuts in unique fabrics, great for a contemporary edge
Clutch Cafe (UK – $$$) – A variety of vintage inspired military, sporty, and casual pants and shorts.
Sugar Cane (Via History Preservation) ($$$) – Excellent jeans made with in-house denim, read for wash instructions and sizing.
Runabout Goods ($$$) – No-frills, lovingly crafted trail clothes in neutral colors.
Magnoli Clothiers ($$$) – Custom made trousers from various eras, inspired by both media and famous figures.
More Workwear Pants – A mix of brands for all budgets, both USA and UK sites.
1957 men’s work shirt, jacket
Coats and Jackets
Few investments are more worthwhile than a good fitting jacket. You can shape your wardrobe around it, count on it through thick and thin, and you will own it for life. I will always recommend getting the highest quality jacket you can afford and letting it grow alongside you.
My recommendations:
- Brown A-2 style bomber jacket
- Navy, olive, or mustard Cossack Jacket (1920s-1940s)
- For motorcycle jackets – Brown barnstormer/bomber/asymmetrical zip up to 1950s, Cafe Racer from 1960s on.
Mister Freedom ($$$) – Impressive variety and style of jackets, well made and with a great history with each piece.
The Real McCoy’s ($$$) – WWII and Vietnam War style jackets, leather, poplin, and canvas.
Standard and Strange ($$$) – Retails various brands specializing in different eras and themes. Great for browsing.
Vanson Leathers ($$$) – Iconic biker jackets from throughout the decades.
Gibson and Barnes ($$$) – WWII, biker, and explorer style leather jackets with historical patches and other decorum available as well.
RRL ($$$) – Core workwear jacket styles from designer Ralph Lauren.
Schott NYC ($$$) – Famous for their motorcycle jackets, 1920s-1960s styles with arm gussets for comfortable movement. Be sure to double check the reviews.
Lost Worlds ($$$$) – Amazing custom fitted leather jackets. Voted the cream of the crop by FedoraLounge and most leather fancier sites.
Kai D Utility For the urban rustic. made in New York City.
Huckberry – Men’s multi brand workwear and casual outdoor styles. Jackets, knitwear, shirts.
Labour Union 1986 (China)- Small batch workwear and casual clothing made and shipped from China. Sizing charts are complicated, email customer service with your measurements before ordering.
More Workwear Jackets – A mix of styles and cuts from various decades.
1954 men’s tall work boots (winter)
Shoes and Boots
My recommendations:
- WWII Impressions Boondocker boot
- Wolverine’s Thousand Mile Boot is a great vintage profile boot that can be found on sale on eBay
- Brown lace-up boots of any kind
- Black slip-on boots (black lace-up for 20s-30s, engineer boot for 40s-50s, Chelsea boot for 1960s)
Viberg ($$$) – Assorted classic boot silhouettes in various different leathers.
Frye Boots ($$) – They can be found at far better prices on other retailers or on eBay.
Red Wing Boots ($$$) – Famous among BIFL circles. Best purchased on sale or secondary sites.
Oak Street Bootmakers ($$$) – Great seasonal sales, solid boots with unique colors and materials. EBay for used.
Blundstone ($$$) – can also be found on sale on eBay. Good for 50s-70s.
White’s ($$$) – Legacy workboot lasts with great arch support. Ebay for used.
Wolverine’s Thousand Mile Boot can often be found on sale and is a great shoe
RM Williams ($$$) – Australian made footwear in dressier Chelsea cuts (1950s-60s style).
Beck Boots ($$$) – While famous for their custom cowboy boots, they also have a distinctly Old West lace-up boot.
John Lofgren ($$$) – The holy grail of shoes, with various work boot shapes and incredible construction.
Huckberry ($$-$$$) – Mixed brand rugged workwear, casual outdoor, farmwear.
Filson – Heavy duty outdoor workwear boots, jackets, pants
Bespoke Post Men’s Shop – Subscription box for the casual male.
Workwear Boots – Lace-up, engineer, and other classic boot and shoe styles.
Read More
- 50 Men’s Vintage Reproduction Clothing Shops
- 1910s Men’s Workwear History
- 1920s Men’s Workwear History
- 1930s Men’s Workwear History
- 1940s Men’s Workwear History
- 1950s Men’s Workwear History
Shop All Men’s Workwear and Casual Clothes Here
