1920s Men’s Vintage Casual Outfit Ideas

If the trend for men’s vintage style going more and more casual wasn’t already in place, the pandemic certainly accelerated it.  Sales for men’s suits and neckties took a deep nose dive, while the demands for sweatshirts and vintage T-shirts exploded. Will it reverse when the pandemic subsides? I doubt it.  I think suits may come back in the future, but it isn’t going to be anytime soon.

So what is a man supposed to do with a closet full of vintage suits? How can he make his classic vintage wardrobe work in today’s world of casual fashion? This is the question Oscar and I set out to answer for you (and honestly for Oscar too) in partnership with MensUSA, who provided most of the clothing for this article.

Young Teenagers in Working Class / Casual Clothing

MensUSA has long been one of my go to sites for affordable vintage inspired suits and trousers (mostly Italian design, made overseas). While the designs and fabrics lean more modern or classic, the price point is what most shoppers are looking for as a starting point on their vintage journey. Now that we have a handful of the clothing to review, we can more confidently recommend their clothing.

The following outfits were put together starting with a full suit and working our way down to casual/workwear. The outfits lean towards to 1920s, but could certainly worn for earlier and slightly later decades (1900-1940).

Suit to Workwear

I requested a brown three piece suit with wide fitting trousers and received a 3 button, dark brown, single breasted suit by brand name Caravelli. Brown tends to be a good suit color that feels less formal than blue, grey, or black. I like that the suit vest came with notch lapels (a very 1920s vintage look) and that the jacket lapels were also wide, instead of the current skinny lapel trend.

Oscar’s favorite piece from the set is the trousers. With a single pleat the fit is a true wide leg (22 inches) with a high waist (16 inch rise). I would buy this suit just for the pants!

Instead of a collared dress shirt, we paired the suit with a blue-grey collarless (mandarin collar) button down shirt. Not having a dress shirt and tie takes this classic suit down a notch in formality while also increasing comfort.

Taking off the suit jacket reveals the collarless shirt more. Changing the hat from a brown fedora to a soft newsboy cap, also takes this outfit into a more casual or vintage workwear space.

Going even further, removing the vest and replacing it with brown suspenders places this look perfectly in the 1920s (ideally, suspenders should be button-on instead of clips).

Oscar also layered the collarless shirt over a thin white Henley shirt which mimics men’s 1920s underwear (long johns). We love this look. It is very “in” and “trendy,” yet also casual without breaking vintage traditions.

In this view, you can see Oscar’s two tone (brown and black) wingtip Oxford shoes by Forezi, the same shoes seen in Boardwalk Empire. MensUSA carries an assortment of wingtip shoes at a more affordable price point than these.

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Casual to Trendy

The second outfit we chose to review began with the best selling wide leg trousers on MensUSA. These were a bit of a disappointment. The width was only 20 inches at the ankle and the rise was not a high-waist but a moderately low waist (12 inch rise).  The waistband has a adjustable elastic band inside that Oscar didn’t love. If he went up one size it may not have been an issue. They are a Polyester/rayon blend, not wool, as listed.

They trousers work well for the outfits anyways, but our preference was for the suit trousers, which unfortunately are not sold as separates (although I asked MensUSA to consider it for the future).

For this casual outfit, we used the same Henley shirt, suspenders, and two hats above, paired with black lace up boots. It has a Peaky Blinders vibe, doesn’t’ it?

Because it was still fall when we shot these photos, we wanted to add one more outerwear piece to this look. Inspired by the clothing we found, we picked this camel hair colored coat as a compromise between a full length coat and short jacket. Oscar loved this coat so much it became a regular part of his non-vintage daily wardrobe. The fabric is very soft and the lining is elegant. The only issue he has had is the lining separated from one arm at the seam. Oscar tends to be brutal to his clothing so I am not surprised it needs a repair like this.

How did we do? Do you have a few ideas on how to dress down your vintage suits into relaxed vintage looks? Can you see yourself wearing this looks everyday and not feel “too vintage?” Oscar certainly can and does.

After wearing these clothes from MensUSA, I can safely confirm we still recommend them. They are not reproduction vintage clothing (with the high price tag to match) but they are good beginner pieces for everyday wear or occasional specialty wear. The website is outdated and lacking in clear photos, accurate descriptions, and current inventory counts. They are aware of this and are working on a new website. Just so you know, you may not get exactly what is listed/described but something close. It wasn’t an issue for us, but could be for other shoppers.

Here is one more look we previously purchased on MensUSA. A blue Zoot suit. Love it!

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