How to do I wear vintage style men’s clothing every day? What are good brands to start with? What are the essential vintage clothes I need to buy? What do I buy my boyfriend/husband/partner for Christmas? These are some of my favorite questions to receive and answer. Oscar and I have been dressing in vintage style clothing for at least the past 10 years, although we don’t always try to wear them every day. We have browsed thrift stores, sleuthed vintage shops, purchased cheap new clothes, and spent a small fortune on vintage reproduction clothes. We haven’t tried every brand out there, but I think we may have enough insight to get you started in the right direction without breaking the bank.
Although I, Debbie, am writing this, Oscar weighed in and agrees with my selection.
Men’s Vintage Suits
A full two or three-piece vintage suit is an essential part of any men’s vintage collection, especially when working in a traditional office environment or out and about in the evenings. Oscar usually only wears his suits for vintage themed events. We started out finding suits at the thrift store, which was never easy. We looked for a suit jacket or sportcoat that fit and did our best to find coordinating new pants. Sometimes we would get lucky and find a matching suit and pants or even a three piece suit combination. We have also occasionally picked up vintage ’50s-’70s suits at vintage /antique clothing stores.
Online, a lot of collectors look at eBay or Etsy listings for suits in their size. Oscar is 6’2, so finding tall enough vintage clothing is next to impossible. That’s why we splurge on new classic suits like those at Paul Fredrick, Brooks Brothers, Jos A. Bank, Perry Ellis or reproduction suits. Reproduction suits, or custom made suits, will cost $600 and up but it is a worthwhile investment to have at least one nice suit when attempting the vintage lifestyle.
Vintage suits come in single and double breasted jackets and solid or patterned colors. Navy, grey, and brown are the three colors that are always in fashion — never black. Black suits were only worn for formal events. Add to your collection an ivory linen suit or striped seersucker suit for summer and you can fit into almost any decade and season. You might be asking yourself: Single or double breasted? Vest or no vest? Belt back or plain back? These are details you get to decide based on the decade/look you are after. Look at these article for help: 1920s suits, 1930s suits, 1940s suits, 1950s suits, and 1960s mod suits/1970s leisure suits
Here are some of Oscar’s suits:
Men’s Vintage Clothing: Shirts
If you plan to wear vintage style suits, you will need some dress shirts. At first glance a dress shirt is a dress shirt, but certain decades introduced new collars and colors that, when, worn elevate your vintage suit fashion to another level. To start with, the 1910s and 1920s favored the round white collar, sometimes called a club collar, banker collar, or penny collar. They were usually detachable which made them easier to clean and replace, but now shirts can be bought with the collar attached. Colors where hardly just white. Vertical blue stripes or other pastel colors in the mid-’20s made these shirts interesting on their own. In the ’30s and ’40s, collars were attached again in matching colors, but the sharp Spearpoint collar became the new trendy shape. The tips were 2.5 to 5 inches long and pointy. Shirt colors ranged from jewel tones to pastels, solids to stripes. Yes, white was an option too, but it’s so boring when all these other fun colors are out there. By the ’50s, dress shirts mostly were white or blue with the classic straight collars you see today.
Oscar loves the dress shirts from Paul Fredrick. You order them by neck size and sleeve length, and they come in all sorts of colors, patterns, and sometimes even contrasting white collars. You can choose between the classic fit (which is wider and more vintage) or the slim fit (which is tapered and more modern). You can also get French cuffs or standard cuffs. ALWAYS, if you can, get French cuffs. It is more vintage, more unique, and certainly more fun to add cufflinks. Since Oscar tends to lose cufflinks quickly, we have been purchasing cheap boxed sets on Amazon.
Casual men’s vintage shirts are what Oscar wears on a daily basis. He looks good in the ’50s to ’70s best, so his wardrobe is full of button down camp shirts (also called bowling shirts or revere collar shirts) and Hawaiian shirts. He also wears a lot of white Guayabera shirts in summer, which is a great ’30s look. He buys these styles from Cubavera, Blair, and lately, he has been wanting more retro knit polo shirts, which we have found on Amazon, TopMan, and Madcap England (Amazon UK). For winter plaid shirts, I like Pendleton and L.L. Bean for some of their authentic vintage designs. Denim work shirts and clothing is a big trend now in the UK and USA.
Vintage Men’s Pants/ Trousers/ Jeans
Moving on to bottoms, most vintage men’s pants from the mid-’20s to the 1950s were high waist and wide leg dress trousers. Even in casual attire, men wore flat front and later pressed or pleated wide leg pants that fit above the belly button. Most were cuffed at the hem, too, although that was a matter of personal taste.
Wide leg pants are not easy to find. Locally, you can sometimes find them in Urban, Latino, or Italian clothiers. Online, I have good luck with MensUSA, MensItaly, and sometimes Amazon. I also like Paul Fredrick’s pants, because while they are not too wide, they have a more classic higher waist and width than most low-rise modern fit skinny pants. Jos A Bank is good too, especially their formal tuxedo pants or traditional fit suit pants. Remember to order vintage style high rise pants with a measurement around your belly, not your low waist / hips!
Historical Emporium’s pants are for good for turn of the cnetury and early 1920s straight leg styles and vintage workwear. Run and Fly has groovy ’60s and ’70s pants, both skinny and bell bottom. Levi’s has a vintage line of jeans from the 1890s to 1980s, although they are not cheap. Remember to order vintage style pants with a measurement around your belly, not your low waist / hips!
Reproduction men’s vintage pants are a nice investment if you can’t get vintage in your size. Fabric, style, and price ranges are all over the map, with the best quality coming out of the UK. See the list here.
Vintage Men’s Vests and Suspenders
You don’t have to wear a suit to get a vintage look. The trend right now has been to ditch the suit coat and opt for only a suit vest with a pair of high waist pants. Hipsters are wearing skinny pants with this look, and while not accurate, it still looks vintage. If you are going to wear a vest, choose one with a collar for an early vintage look, double-breasted for a ’30s style, or single breasted with no collar for all other decades. Feel free to mix and match pants, vests, and shirt colors. It is fun to break the rules with this casual look. Amazon has a ton of affordable vests to choose from. I link to my favorites vests here.
Suspenders under or instead of a vest is another nice touch. Button-on suspenders look especially vintage, but that will require adding buttons to most of your pants. Clip-on suspenders are fine too, but be careful of cheap brands. The thinner the elastic, the more it stretches too much, and the more likely your pants will sag within the hour. Oscar has suspenders in every color and style imaginable – choose whatever you like. You can also just wear a belt, but I think belts look odd paired with vests. Shop suspenders.
Vintage Men’s Sweaters and Sweater Vests
Besides button-down vests, a very vintage winter or spring look is to wear a sweater vest or cardigan vest. They could be worn alone or under a sport coat. For the most vintage look, choose either a plain color with a chunky cable knit or a smooth vest with a bold pattern like argyle, Fair Isle, or colorblock (two tones). If your pants are high waisted, your vest will look best if it is short waisted. A wide waistband is a nice touch too. Short vests are hard to find, so don’t worry about it right away. I usually find good knit vests at Brooks Brothers, especially on sale in the summer. Shop sweater vests.
Round neck or V neck sweaters/ jumpers and cardigans can work the same way as sweater vests. Layer them over a shirt and tie and under a sports coat for a wintry warm vintage style. Fair Isle, Argyle, and Nordic winter/Christmas designs are the most collectible sweaters. Solid colors are nice when paired with a patterned sport coat. In spring and summer, the ivy league/collegiate/preppy/tennis player look pairs a white or ivory cable knit, V neck sweater or sweater vest with matching trousers. You could also get a fisherman/Aran /Irish knit sweater and pair it with colored trousers and a tweed flat cap. The look is unmistakably vintage.
For more of a retro take, look for sweaters with geometric prints or ugly 80s sweaters.
Another collegiate style is the Letterman sweater, with a big school letter on the front or sleeves. This look might venture too far into the “costume” category for some, but this preppy look is about to hit a revival. You can see it now in designer collections like Ralph Lauren and Gucci.
The other vintage sweater I like is the large shawl collar cardigan, preferably in a chunky cable knit. It is a ’20s design that came back in the 1950s. It is back in style now, so there are many more options than there were a few years ago. It looks so warm and cozy, too. Oscar doesn’t normally like or look good in sweaters, but this style is an exception.
Vintage Men’s Jackets and Coats
Keeping warm in winter doesn’t mean you have to resort to wearing puffer jackets. The most classic vintage coat is a long wool overcoat — and by long, I mean below your calf. Coats shortened up in the mid-1950s, so a long coat definitely says vintage regardless of the other details. Your coat could be single or double breasted with a large collar and big pockets. Belted trench coats are another classic, especially for rainy weather. The shorter navy pea coat is another timeless vintage coat that is not long, but still very vintage. I usually find good coats in thrift stores –just be sure to avoid modern tech fabrics or the use of zippers.
The downside to overcoats is they are heavy, not very weatherproof, and potentially too warm. Modern heating created new opportunities for lighter vintage jackets to replace long coats. Some of the classics are wool, suede, and leather bomber jackets or flight jackets. They are short with a zip front, cuffed sleeves, and open bottom. The military A-1 and A-2 flight jackets usually have large pockets on the fronts. Wool cloth versions could be solid dark colors or plaid. Many were lined in sheepskin or quilted cotton. Without a lining, they act like a light windbreaker, making them good for layering over vintage sweaters. Shop men’s coats and jackets.
Another short leather jacket to consider is the motorcycle jacket, especially if you are into the 1950s James Dean look. Motorcycle jackets look more vintage if you pair them with nice trousers instead of jeans. Rockabillys will disagree with me on that point. It is all in what you pair with it, how you wear your hair, and the accessories you choose.
The plaid jacket remained a vintage classic in other styles too, but in the 1940s and 1950s, the bomber jacket got a facelift in a new lighter material called Gabardine with a plaid interior lining (now called the Harrington Jacket). It was a golf jacket or workman’s and military men’s uniform jacket for years before it became trendy with the college kids. Oscar wears his US Navy jacket as a light coat. It is the same classic style you can buy in almost any men’s clothing store. Oscar is on the hunt for a ’50s two-tone Gaberdine jacket to replace his well worn Navy jacket. Shop men’s coats and jackets.
Vintage Men’s Shoes
Setting aside clothing, we can focus on the next most important purchase — shoes. A vintage gentleman mostly wore Oxford shoes in brown, black, or two-tone patterns. You can still buy basic cap toe or wingtip brown or black Oxfords in most stores. Two-tone patterns are much rarer, but are crucial for a vintage look. Stacy Adams is an affordable, stylish brand to start with. We love their wingtips and lace-up boots. Allen Edmonds and G.H. Bass are two other solid brands that sometimes offer vintage classics, like the saddle shoe.
Loafers are the other essential vintage shoe to have. Penny loafers without tassels were worn in the mid-century with all casual clothing (not sweatpants casual). In summer, the suede-like nubuck in ivory is a classic, as are boat shoes. Men like Oscar wouldn’t be caught dead in most of these. Too clean cut for his daily rock n’ roll style. He prefers classic Converse shoes for most looks with jeans. Consider the original PF Flyers shoes as well.
Boots are the biggest vintage trend in men’s footwear now. Thanks to the ’20s revival, classic vintage men’s lace up boots are being worn with vintage and hipster clothing. Simple is best and quality is king. Frye boots and Stacy Adams’ Madison are perpetual favorites. Also, consider the pull-on Chelsea boot. They have been around since the 1800s, although most people associate them with their revival in the 1960s.
Vintage Men’s Hats
Fedora. Every man needs a wide brim fedora hat, not the skinny snap brims you will see a lot today. There has been the stigma of the Fedora with guys who still live in their mother’s basements. It is all how you wear it. If you just put on a fedora, don’t expect that alone to make you look vintage. You have to style it with the rest of your outfit. The shape and color of your fedora will vary a little based on a specific decade you want to emulate, or simply based on what looks flattering on you. Oscar has a big head, so he needs the widest brim hat he can find to balance out his proportions. Ideally, a 3-inch brim is good on his, but he has a few 2.5 and 2.75 inch brims that look ok too. His favorite is the Indiana Jones Hat.
A casual cap is another essential hat. The 8-panel newsboy was a working class day hat or upper class sport cap. Later, the slimmer Ivy cap entered the picture. Tweedy, plaid or herringbone fabrics have the most vintage look. Shop men’s hats and caps.
If you despise hats, all you need is a good barber and some hair products to maintain a vintage haircut. Most trendy men’s hairstyles today are based on vintage cuts. Kudos if your barber also does straight razor shaving.
Putting it all together
If you need more outfit ideas, or examples of how to put it all together look at these other articles:
- 1920s men’s outfit ideas
- 1930s men’s outfit ideas
- 1940s men’s outfit ideas
- 1950s men’s outfit ideas
- 1960s men’s outfit ideas
- 1970s Disco outfits/men’s fashion
- 1980s Men’s fashion
- Men’s fall/winter outfit ideas
- Men’s workwear clothing
More online resources:
- Facebook’s Fedora Lounge /vintage menswear groups are a great place to ask questions and get help with your outfits.
- Ethan W. blog StreetxSpezza shares style guides, shopping tips and some history about vintage and classic menswear.
- Ivy Style is an entire blog about vintage (and current) ivy league style
- Gentlemen’s Gazette – fellow fashion history menswear blogger about classic menswear
- Dandy Wellington(Instagram) has impeccable vintage style and amazing vintage jazz music
How do you dress vintage every day?