Recently Jessica, at Chronically Vintage, received a question from one of her readers about what men should buy to start a vintage style wardrobe. She suggested men have a well tailored suit, blazer, vest, hat and tie. I thought her classic picks were good standard pieces that have stood the test of time and indeed should be added to a vintage style wardrobe.
Oscar’s 1940’s Swing Suit with Fedora Hat
Being married to a vintage loving husband, I have a different perspective on what clothing and accessories make a man look instantly vintage. Oscar and I brainstormed and came up with our own top 10 list. You can take just one of these items and add it to your contemporary wardrobe for just a hint of vintage or mix and match them all for a VERY vintage vibe. The list isn’t for one specific decade, instead it represents the best of all the decades as well as the styles that my husband gets the most compliments on (from other men).
10 items you need to start a men’s vintage style wardrobe
1940s Men’s Style Fedora
1. A vintage style fedora. A wide brim felt fedora with wide hat band was in vogue from the 1920s to 1950s. Brims, band and colors changed a bit over the years but overall just wearing a Fedora hat instantly makes a man look 1. vintage and 2. handsome. Swoon, sigh, faint.
Good colors are black, dark brown, or grey. A wide brim is at least 2.5 inches. You could go with a much skinnier Stingy brim fedora and pull of a late ’50s Sinatra look. Just be ready to serenade all the ladies who will fall at your feet.
2. Vintage tie. While most items I recommend can be new vintage inspired clothing, the necktie is the one item I highly encourage you to buy vintage. Men’s vintage ties from the 30s to the ’60s were hand painted with picturesque scenes and colorful Deco prints. Even the more subdued ones, like this vintage Art Deco tie from the 1940s, stand out in your wardrobe. My husband gets the most complements about his ties whenever we go out. I wish fun pattern ties would come back again. Not in the kitschy ’80s way, but in the classic artful vintage flavor.
3. Suspenders. Whether you wear a suit or just a dress shirt, a snazzy pair of suspenders will not only keep your pants up (see pants below) and hide your middle aged belly, but look incredibly retro. Basic black is a good staple, but don’t be afraid to channel the ’50s with stripes, checks, comical patterns and fun colors. Go the extra mile and get button on suspenders instead of clip on. You will also need to have buttons sewn on to the inside of your modern pants for the suspenders. The overall look is clean, classy, and polished.
Oscar in Fedora hat, Vintage tie, Pinstripe pants, and Two Tone shoes. Very Vintage!
4. High waist trousers. These are going to be tough to find, both vintage and new, but well worth it. Prior to the ’80s, men wore their pants at or above the belly button. It’s a very flattering look because it adds height if you are short or stocky, is comfortable (no tight waist bands to loosen after a big meal), and looks better with your vintage tie (ties were often shorter- high waist means no gap between pants and necktie).
Avoid pleated pants. One single crease on each leg is vintage, lots of gathers at the waist band is not vintage and generally looks horrible on men- vintage or contemporary. Very wide leg pants are also very vintage but harder to find.
Colors can be pretty much anything. My husband wears his pinstripe pants the most often. There is just something very vintage about the look (hello ’40s.) The stripes should be wide enough to be noticed, not so subtle you need a magnifying glass to see them. I also recommend buying new pants one size up. This will give you a little more waist height and a looser fit for your suspenders to do their job. While you take your trousers in to have suspender buttons added, ask them to cuff your pant legs too for a 20s-40s look. Just one extra step to set you apart from the crowd.
Shop vintage style men’s pants here.
5. French cuff shirt. French cuff shirts, also called double cuff shirts, are very vintage. Back in the day, men’s shirts were buttoned closed with a snazzy pair of monogrammed cuff links. It was the one piece of men’s jewelry that had the most personality. A common gift, it was a way for men to carry a piece of a loved one with them throughout the day. Having your cuff links on your French cuff shirt peek out from under your suit jacket sleeve is a little vintage touch that says you are a man of class.
6. Two Tone Shoes – If nothing else, get a pair of two tone shoes and you will always look vintage. Go for either black and white saddles, brown and tan, or white and grey oxfords. The dark and light contrast makes you noticeable regardless of what else you wear. They are often thought to be an informal or sporty shoe for men, but my husband wears his black and white wingtips with his tuxedos and looks very dapper.
7. Vest – Most men used to wear three piece suits. If you are going to invest in a good tailored suit, I highly recommend you get a matching vest to go with it. If you want to go for a more informal style, any vest in a shade that matches your pants worn over a shirt (and suspenders) will give you that vintage sporting look. Single or double breasted vests are welcome. The later is more formal but also more unique. Unique + vintage = good.
8. Hair pomade – I know, I know. Not clothing, but an essential product to have in your arsenal of vintage goods is thick hair pomade. Don’t use hair gel. Get real pomade which is often found in the ethnic hair styling section of your local drugstore. You can still buy vintage recipe pomade, too, like Murray’s. Next, learn a few basics to men’s hair styling by the decade. Slicked straight back hair works great for the ’20s and ’30s. Deep parted to one side is good for the ’40s and ’50s. Anything else is fancy stuff that probably requires you to grow out your hair and get it styled by an old fashioned barber (bring pictures to help them).
9. Tuxedo – If you haven’t worn a Tuxedo since your wedding or high school prom, it is time to revisit the sexiest suit a man can and should own. I don’t know what it is, but there is something about what a tuxedo does to a man that makes ladies swoon (ladies, am I right?). It is also the one go-to look that spans the entire 20th century for any event after 6pm. Since ladies love to dress up in their finest vintage frocks whenever they can, you, too, will need a fine tuxedo to match.
There were some changes to the tux after the 1920s, but nothing too significant. Peak lapels are the most vintage followed by the unique shawl collar lapel (hello Sinatra) and the most common notch lapel. Notch lapels are all over contemporary tuxedos which is why we like to avoid them. They look too normal, not vintage enough.
You will need a good pair of tuxedo pants, white French cuff dress shirt (no pleated tuxedo shirts please), black patent leather shoes, optional black or white silk vest, and a black or white silk bow tie (learn to self tie one). Do not wear cummerbunds (yuck, tacky!) or brightly colored/patterned vests.
The cost of Tuxedos can be very affordable. I would recommend buying yourself a good one at some point. Renting can expose you to different styles that you can try before you buy. Selix is probably a chain in your town that has a very diverse selection of Tuxedo styles. If you want to buy, see if you have a Jos A Bank nearby. I have some Tuxedos listed here, too.
Pocket Square
10. Pocket Square- The last little accessory you need to wear with any suit, day or evening is a silk pocket square. Match your tie if you can. Learn a few ways to fold it and pick the one you like best.
That’s it! The top ten from a man who actually wears all of these clothes frequently. You can start with just one item and gradually add to it. Finding vintage menswear can be tough depending on your size, so it’s perfectly ok to use new clothing with a vintage or classic style to it. Some things like ties and cuff links will be easy to find in antique stores (and prices are often very affordable too). Whenever possible, buy vintage, but don’t worry if you can’t.
Gentlemen, what items would be on your top 10 list?
Debbie Sessions has been teaching fashion history and helping people dress for vintage themed events since 2009. She has turned a hobby into VintageDancer.com with hundreds of well researched articles and hand picked links to vintage inspired clothing online. She aims to make dressing accurately (or not) an affordable option for all. Oh, and she dances too.
