I love vintage style, but there are a lot of things that set me apart from other enthusiasts. While many enjoy period hobbies, I definitely don’t swing dance and I don’t watch a lot of old movies. It comes as a shock to some, as the latter is how most people I know came to be involved with vintage menswear. Sure, I may have seen a few of the big name classics, but it’s not something I consider monumental in my personal style journey; that doesn’t mean I haven’t been influenced by them, nor that I’m unfamiliar with them. Screenshots of films, promo shots, and candids of Golden Era actors used to fill my Tumblr. So with that, it’s no surprise that Jimmy Stewart was someone I saw often.

As you may know, Jimmy Stewart was a movie star during the “Golden Age” of Hollywood. Initially, he had attended Princeton studying architecture, but he soon found himself acting in small performers troupes. Eventually, he moved to Los Angeles, encouraged by Henry Fonda, and began his career in Hollywood, starring in almost 30 films until he enlisted in the Air Force during WWII. Stewart currently holds the distinction of holding the highest rank of any other actor who served in the U.S. Military.

For me, the appeal of Jimmy Stewart stems from how natural he makes everything look. I was never a fan of the prim and proper Cary Grant photos (who is loved for his 1950s-1960s style) or the “badass” look of Humphrey Bogart; I always felt more drawn to the candid and lifestyle shots of Stewart. Admittedly, Rear Window and It’s a Wonderful Life are the only Jimmy Stewart films I’ve seen, but I am familiar with his work (and style) through the countless images I see.

One thing in particular that I appreciate is that he had a very classic style. With flannel suits, striped shirts, and the occasional foulard tie, his style is a preview of some of the stuff you can see today. While the suits are cut in the classic Golden Era style (broad shoulders and wide leg pants), it’s not done in a costumey way. The fit is always on point, with a tapered waist and trousers that seldom break, which is a hard contrast to what most people think of when it comes to vintage style. He was sharp for the times without subscribing too much to the trends that we covered before.

During the 1930s and 40s, many actors would wear their own clothes in films. Because of this, men like Stewart were perpetually well dressed, both on and off the camera. One of my favorite outfits of his appears in a photo where Jimmy is sitting on a white fence, in which he wears a wide peak lapel houndstooth tweed jacket with navy trousers and white bucks. It really goes against the common style rules that we abide by today, like combining tweed and summer shoes. He does employ the “sprezza-tie,” with blatant disregard for its length and whether or not the back blade is showing. The entire outfit seems to be slightly ivy in its execution, as other pictures show that he was, in fact, wearing a striped cloth belt.

Another outfit that comes right in time for spring-summer, is Jimmy wearing a gaucho style polo shirt with the same peak lapel jacket. Not only is this cool because it showed that he reused a lot of the same pieces, but it also shows a little bit of the unique, trendy items of the 1930s. Gaucho shirts are largely similar to polo shirts but they featured a deep loop button placket and spearpoint collars; the hems were usually all ribbed. They grew in popularity among Golden Era actors during the late 1930s, and were seen on many stars, including Jimmy Stewart.

Gaucho-style polo and a tweed peak lapel jacket.

This image speaks wonders about Stewart’s style, though it might be a costumer’s idea. In a huge contrast to the well put together Cary Grant, Jimmy wears an unfastened chalkstripe DB suit, with a striped shirt and striped tie. Talk about sprezzatura, right? I remember seeing this years ago being inspired to experiment with triple pattern mixing–even if it’s all stripes. It’s hard to see people do that today, let alone make it look so natural, which made vintage style appeal to me even more today.

Jimmy Stewart in Philadelphia Story

Obviously, there are more great looks from Jimmy Stewart than the three I’ve examined here. It’s all very indicative of classic 1930s-1940s style without getting into the bold or flashy styles of Fred Astaire or George Raft (both of which are inspirations nonetheless). I’ve included a small album of my favorite looks from Jimmy Stewart for you to look at. I think that he was pretty consistent with his look, which you can definitely see in his later years. He may not have the spearpoint collars, but he still rocked the collar bar and the runaway collar until his death in 1997. Honestly, I think a lot of his attire can be used as inspiration today, whether you’re going for a true vintage look or something more contemporary. I certainly look to him quite a bit.

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Ethan Wong

Ethan Wong lives right in the middle: he’s too modern for the vintage scene and yet too vintage for classic menswear. When not at work, he spends his time writing and taking pictures for his blog, Street x Sprezza, which is all about bringing vintage style into the modern day. With a large collection of thrifted vintage and contemporary clothing, he often wonders when his closet will finally implode.

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