Tailoring a $3 Thrifted Suit: A Brown Chalkstripe Three Piece

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I’m always on the lookout for cheap, vintage suits. You’re guaranteed to find great suits at vintage stores like Joyride or from sellers like Benny, but there’s nothing like the feeling like scoring a great piece at a thrift store.   If you look hard enough and have great patience, you can definitely find some cool stuff!  And sometimes, you’ll find it on a sale day where your suit will cost $3.

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Tailored Casual with the Tucked-in Short Sleeve Shirt

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If you can’t already tell, I really document my casual outfits.  At one end, I typically dress down a suit or blazer with a polo shirt.  For the other side of the spectrum, I go full 1990’s inspired, with a faded sweater and some jeans and sneakers.  For this article, I decided to delve more into into an outfit that is more “casually tailored”, a term frequented by style bloggers like Dan Trepanier.  My version looks toward the cool summer/vacation styles of the 1930s-1950s, where tucked in shortsleeves were all the rage.  It’s perfect for summer, since you’re probably looking to leave your long-sleeve shirts at home.

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A Tailoring Experiment: Pleated Trousers

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Now that we can agree that pleats are cool, it’s time to try them out.  I noted in my previous article that it is difficult to obtain pleated pants with the necessary details (high rise, slim-straight).  So when I was presented with an opportunity to try and tailor down some 1980’s baggy, double pleated pants, I took it.  If it worked out, I may have found a way to get pleated pants at an affordable price! If not, I’ll be out a few bucks, but I know it can’t be done. Let’s find out!

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Pleats: They’ve Always been Cool

Just look at those pleats, courtesy of Permanent Style.  If you show this to any mainstream fashion guy, he’d recoil immediately.  Flat-front pants have been the way to go for the past few years.  Favoring the clean look, the mainstream #menswear community has renounced all ties to the dreadful 1990s business look.  But classic enthusiasts in the community have always favored pleats and have still had them in their trousers without looking terrible!  Here, we look at the brief history of pleats and how they have evolved through menswear.  Hopefully you’ll agree that pleats are, and always have been, cool.

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