Last week, I mentioned the trend for wanting/wearing vintage casual clothing is in high demand this year. Request for men’s clothing is usually prefaced with “I don’t want to wear a suit” or “how can I work with clothing I already have?” While Oscar thoroughly enjoys wearing vintage style suits, the majority of guests at events we attend do not have the same appreciation — or perhaps it is a lack of budget. Three piece suits are not common in our contemporary wardrobes and are expensive to invest in for what is ultimately only occasional wear. I understand the dilemma. So what is a man to do? While casual clothing is less common than full suits, starting in the 1920s, men were moving towards leisure or sporty styles, leaving us a handful of non-suit options to wear while dressing vintage or retro.
To illustrate these casual styles, I purchased some new clothing and asked Oscar to volunteer as my model. Seeing clothing on a real human being is a bit better than a roundup of catalog pictures or staging on my man mannequin anyways.
For this outfit roundup, I focused on the 1940s. Coming off the 1940s Style Guide series, I realized I didn’t have many examples of men’s outfits. Looking at pictures of various menswear from the 1940s as inspiration, I created these six casual outfits that incorporate thrift, new modern, and ’40s reproduction clothing. Most of these looks can be achieved with what is in a typical wardrobe already, with optional purchases of a few accessories like a hat, vest, shoes, or suspenders. These looks were also part of the 1930s and 1950s, making them versatile enough for a general retro-inspired look.
Men’s Vintage Casual Basics- Shirt and Pants
Most men have a dress shirt and pair of dress trousers in their closet. This is the base for vintage menswear too. The difference is in the cut of the clothes and the accessories. 1920s to early 1950s pants were wide leg and high waisted. Wearing a pair of these pants will instantly take you back to the mid-century. You can wear classic fit trousers for a mid 1950s style and even slim fit trousers will give a ’60s look.
Next, add a dress shirt or sports shirt. I look for shirts with wide collars for the most vintage look and leave the top unbuttoned for a semi-casual statement. Consider bold colors and patterns, shirts with one or two chest pockets, and a loose (not slim) fit. Always wear them tucked in with high waist pants and a simple leather belt. You could also wear suspenders instead of a belt for another retro look on trend now. The button on suspenders are best, but snap on will be easier to find.
The Vintage T-Shirt
What if you don’t own a dress shirt and trousers? What then? Well thankfully, there is always a T-shirt. T-shirts came into fashion in the 1940s. Prior to that, they were an underwear item only. Men started to wear them at home without a shirt over them and the trend caught on. Colors expanded away from just white. Striped T-shirts were the most popular because they looked nautical and sailor-ish, and dressing like a fisherman had been trendy since the turn of the century. The look never left vintage men’s summer fashion, even in 1960s when the mods revived it.
Pairing a very casual striped T-shirt, wide leg pants, belt, cap, and canvas boat shoes completes this summer look. The very casual sport cap was an acceptable alternative to straw hats. Ours here is a tan cotton cap but a white or ivory linen cap would be cool as well
The Man in Jeans
It was during the 1940s that the t-shirt and jeans combination became increasingly popular, but it was in the 1950s that James Dean and Marlon Brando popularized the look even more. Just like dress trousers, blue jeans were wide legged with a dark wash and rolled with a cuff. They were usually worn with a clean white T-shirt or button down sports shirt with rolled up sleeves. Popular shoes were sporty black high top Converse styles, leather Engineer boots (for the motorcycle riding rebels), and penny loafers.
The look is easy and very vintage, although you may not stand out as “dressing vintage.” For newbies or those that are hesitant to dress vintage in the first place, this is a great option.
The Hawaiian Shirt
Besides T shirts the other casual vintage men’s shirt was the Hawaiian shirt. Worn untucked (gasp!), they came in tropical prints and themes. They were a perfect casual style in summer. Worn again with classic or wide leg pants and a belt, they set the tone for a retro vintage men’s look that is still popular today. We paired our outfit below with a straw fedora hat, canvas boat shoes, and a flower lei. Vintage? Modern? Both!
Now, where is Oscar’s ukulele?
You could use the same idea above but with a camp shirt or polo shirt instead of a tropical Hawaiian shirt. The look below is 100% vintage 1950s, but you can create the same pleated pant, camp shirt, and two tone shoes look with new clothing as well. Want more 1950s casual clothing ideas? Look here.
The Suit that Isn’t
The above examples are all casual men’s vintage styles at their most leisurely in summer, however for those willing to be a little dressier, there are some better options for cooler weather. If you have a suit or sports coat you can dress vintage semi-casual. Layer a patterned pullover vest with a dress shirt for a casual 1940s style, finishing the look with high waist trousers, two tone Oxfords, a felt fedora hat, and a suit coat (optional). This no-suit-required look is still dressy enough for most vintage events, yet casual enough to satisfy the need for comfort.
Another similar look involves wearing a button down vest in a contrasting color and a patterned sports coat. This mix and match of a shirt, vest, pant, and sports coat were very common in the 1930s, 1940s, and 1950s. I love to pick up sport coats at the thrift store and mix and match them with pants we already own. The combinations can get pretty wild sometimes.
The only look I didn’t source yet is men’s vintage workwear, which is another BIG trend right now. I am working on some examples of these as well as more women’s vintage casual clothing outfits. You might also take a look at this article on retro men’s fall and winter clothes, how to dress for a swing dance, or these outfit ideas by decade:
- 1920s men’s outfit ideas
- 1930smens outfit ideas
- 1940s men’s outfit ideas
- 1950s men’s outfit ideas
- 1960s men’s outfit ideas
- 1970s men’s disco fashion ideas
- Vintage Workwear for Men
Shop new men’s vintage clothing:
- Men’s vintage shirts
- Men’s vintage pants
- Men’s vintage jackets
- Men’s vintage suits
- Men’s vintage sweaters and vests
- Men’s accessories: suspenders, hats, sunglasses
- Men’s vintage shoes and boots
- Mega list of vintage repro clothing brands