Even though we love going sartorial on the blog, we still have a passion for casual style. It’s been 80F for a full two weeks in Southern California and I’ve found myself ditching my ties for open collars and my sportcoats for rolled up shirt sleeves. We’ve talked about sartorial casual, but its always fun to take it down a notch further and wear tee shirts with trousers! It’s a topic we’ve explored 3 times in the past, but this one has a slight nautical twist. The look is perfect for hot days when even a button up is too much.
Wearing tee shirts and trousers is something that you don’t see everyday and as a result, is something difficult to pull off. Most of time, it’s done wrong and makes you look like an old man. Like anything, fit and styling plays a huge role in making the outfit look good! The style is coming back today, mainly through streetwear with some 90s vibes. This and this are some of my favorite examples. Surprising, I know, but I definitely know how to appreciate style of all kinds!
**I’ve dabbled in 90s street style and if you don’t believe me, follow me on instagram.
The first time we explored it, we took some inspiration from the 1930’s and 1940’s and paired a striped tee with off-white cotton trousers. It’s almost a dead ringer for this mid 1940’s look! Note the slim-straight fit of the trousers (with minimal break) as well as the snug fit of the tee. Not too “dadcore”, is it?
Since then, we’ve also explored layering the look with a cardigan or even going semi-streetwear with clean sneakers and a large coat. In this post however, I want to return to the vintage roots of the “tee and trouser” look. As we’ve seen in my first post on the subject, it was a common casual look for guys in the 1930s and 1940s. Back then, denim wasn’t widely worn as a casual pant so men would wear trousers with their tee shirts! Don’t make the mistake of thinking that they were suit trousers; these trousers were made of fabrics like Palm Beach, linen, fresco wools, or cotton in order to keep with the “dress down” feel. For the shirts, plain tees were definitely worn but most men opted for stripes! It provided more visual interest as well as a slight nautical vibe.
I’d also like to point out that loafers weren’t the go-to casual shoe for men back in the day. They certainly existed but shoes like bluchers, spectators, and saddleshoes (or even sneakers by high school kids) were typically worn with the tee and trouser combo since they were the “informal” shoes of the day. In summer time, espadrilles were even worn with the tee and trouser combo.
In early fall of last year, I was able to pick up some white espadrilles (as well as Aloha shirts). These Spanish shoes were very big in the 1930’s and men wore them with their casual combos, especially if they were at the beach! Guys still wear espadrilles today but its typically with shorts, though you can see them (quite oddly) with suits. Putting these extremes aside, I think it would be pretty great if guys took some inspiration from the Golden Era and wore them with tees and trousers, the perfect blend of casual and sartorial! Personally, I find them much more comfortable than leather shoes and much more interesting due to the texture of the canvas and “plain” nature of the construction.
These pictures (and the hot weather) really convinced me to do the combo again,
this time with a clear inspiration from vintage menswear.
With similar styling and fit, this outfit pretty much echoes the first one I tried just with a few details changed. In fact you could say that the color palette changed! Instead of a blue stripe short sleeve shirt, I went with a long-sleeved white and blue stripe shirt to further the semi-nautical ties of this outfit. For pants, I swapped the white cotton ones for navy blue chinos! They’re dark but they help ground the outfit as something a bit more “sartorial casual” than just straight up casual. Lastly, we have the white canvas espadrilles to tie in the spring/summer nature of the outfit. People like to judge outfits by the shoes and these shoes definitely make the vibe. Overall, I think it’s a great modern interpretation of the outfits we saw above!
I wrote a t-shirt article a long time ago but I can reiterate the points here: fit matters. Baggy, semi-tucked tees are a thing with streetwear but I don’t think that its well with a sartorial-casual outfit. Note that the shoulders fit right on the money and that the sleeves/body are cut slim without being too tight. If you want to wear a tee shirt with your trousers, make sure it fits just like you see here. Something snug with a little bit of drape! Trust me, it makes a world of difference.
Also, I feel like long sleeves are better than short sleeves, since they hug the arms more and give you a better figure; the same argument could be said for regular dress shirts. I have this type of shirt in both long and short sleeve just so I have options when making an outfit!
If you’re wondering, this tee is a size small (I’m a 38S) and is one of the soft wash pieces from Banana Republic. I’m not really a fabric expert but I definitely like the feel of this shirt and it served me well during the day! I’d much prefer to find a vintage one, though I’m sure those are hard to find.
Braided belts are cool because of how “casual” they are, even though they are made of leather. Like most of my pieces, it adds a bit of visual interest without being too flashy since the detailing is all in the weave/construction of the leather itself. Please stay away from branded belts with huge buckles like the Louis Vuitton or Hermes ones. The braided leather is understated and goes well with casual suiting (linen, cotton, fresco) to even chinos or shorts! I even prefer it over canvas or o-ring belts; those one’s scream “preppy-teenager-American Eagle” to me.
Unlike the vintage examples, my trousers are flat front. While I do like pleats, there’s nothing wrong with going flat front! I honestly didn’t have a choice since these were from Banana Republic and most mall brands avoid creating pleated trousers. These pants aren’t as high rise as I’d like, but they get the job done right! They’re still cut well enough to have a classic look. Everyone should have a couple of chinos; I’ve worn them dressed up and this post is a great example of using them in a dressed-down outfit. If traditional wool trousers aren’t for you, then these are the way to go. The fact that they’re 100% cotton makes them a warm weather favorite!
And here they are, the espadrilles. They’re well made, breathable/comfortable, and definitely make the entire look. Loafers could have worked with this outfit, but having the espadrilles just add an extra edge that certainly screams “summer” and “casual 1936 style” all at once. They looked great with my Hawaiian shirt and they certainly look great with this. Obviously, espadrilles are the perfect summer footwear short of wearing sandals. For that, I recommend birkenstocks (though I should update the article).
Lastly, note that my chinos are creased and cuffed even though they are a casual trouser. If you guys haven’t noticed, almost every trouser I own has cuffs; I even roll up the edges on my denim! Cuffs (or turn ups) add visual interest since plain bottoms certainly are en vogue in the main circles of #menswear. Personally, I find that cuffs simply look better and give your trousers an old school look. Plus they assist the drape of your trousers by adding weight and even help hold the center crease! The result is a clean look that can always be dressed up or dressed down. Don’t forget that almost every trouser in the 1920s-1940s had cuffs and were creased!
Soft Wash tee from Banana Republic, Aiden Fit Chinos from Banana Republic, Braided Belt (thrifted), Espadrilles (from Espadrille Store)
If you can’t tell by now, we’re strong proponents of wearing tee shirts tucked into your trousers. Just approach it as you would wearing a full sartorial outfit: fit is imperative. If the fit of the shirt or pant isn’t right, you’ll start delving into dadcore and that isn’t a good thing. Baggy (or non-conventional fit) certainly has its place, but that’s even harder to do! So just follow our advice and stick with well fitting garments.
Wearing a tee shirt with trousers is certainly a cool look when done right! Works when you don’t want to wear an actual button up shirt or if you feel like the Sartorial Polo. The outfit is something a little bit hipster since it’s something you never see but it’s worth checking out especially if you’re interested in exploring how people dressed down back in the 1930s and 1940s.
Let us know what you think of this article by commenting below! Did you like the nautical vibes of the outfit? Would you wear espadrilles? I want to know!
Always a pleasure,
Street x Sprezza
Photography by Spencer O.
PS: These glasses are not vintage! They’re actually super cheap plastic ones from Eye Buy Direct! The frames have a bit of a 90’s dad vibe that I really like, so I got them! Yes, these are prescription but the total only came out to be $35! I wouldn’t recommend going with this company if you want a high quality pair of glasses. If you want to experiment wth different frame styles and get some flimsy ones, then go ahead! I currently have 3 different ones so far, all prescription!