Faded jeans and tailoring

When I look back on my most worn items in the last 12 months, one garment reigns supreme.

That garment happens to be my old, worn, frayed and faded Levi’s 505s. I love them; they’re comfortable, they look good and they’re damn versatile. They’ll go with a sportcoat, shirt and tie (or no tie), western shirt, shirt jacket, T-shirt… anything.

The colour and the texture make them easy to pair with a wide range of seasonal and trans-seasonal fabrics. Tweeds, woollens, camelhair and cashmere pair well during the cold season. Silks, corduroys and cotton twills play nicely in the transitional seasons. Linens, seersuckers, madras and textured high-twist wools play nicely in the summer. The sheer volume of possibilities enabled by one pair of beat to hell jeans surpasses anything else I can think of.


It took me some time to mull over in my mind exactly what my influences in wearing faded jeans with tailoring came from. There’s that one picture of Ralph Lauren in double denim with a tailored jacket on top, which was undoubtedly an early inspiration (and something I recently paid tribute to). Tom Selleck in Magnum, p.i. was certainly an influence in that I knew I could throw a tailored jacket over the signature aloha shirt and faded jeans look, though I don’t recall if he ever actually wore such an outfit on screen.

Younger Ralph Lauren in double denim and tweed jacket

I know there are some other oft-cited pop culture examples of jackets with jeans like Richard Gere in American Gigolo (though I was wearing jeans and jacket long before seeing that film) and that one paparazzi picture of Harrison Ford sporting the combo which seems to be perpetually present on my Instagram explore page, always from some random repost account. With Seinfeld having a big return moment over the last couple of years, many examples of Jerry Seinfeld, Jason Alexander and Michael Richards have been hitting people’s fashion mood boards too.

Richard Gere blazer and faded jeans outfit style
Richard Gere in American Gigolo. The only time I’ve seen a notch lapel DB that didn’t instantly look wrong.
Michael Douglas blazer and jeans outfit Basic Instinct
Michael Douglas toward the end of Basic Instinct.
Billy Joel 52nd Street jeans and tweed jacket outfit style
Billy Joel shot for the 52nd Street album.

I can’t even remember the first time I actually tried wearing faded jeans with a jacket myself. Only that it worked for me, because I love to do it now.


While I may have had the plausibility of the idea cemented in my head from seeing it done by others, I’ve never really found myself trying to emulate what others have done. Once I know I can do something, I tend to just incorporate it into my own point of view, and let my own eye put the pieces together.

I don’t adhere to a specific style in my taste in clothes, though when it comes to pairing jeans and tailoring most is within the ivy/prep aesthetic.

RLPL jacket, custom OCBD, black western belt from Midwest Trader, black vintage penny loafers, black silk knit.
Polo Ralph Lauren madras jacket, custom OCBD, vintage belt, Clark’s desert boots.
RLPL jacket, vintage Country Road poplin button down, Crockett & Jones shoes.
The aforementioned PRL madras, with Ralph Lauren polo and CDBs.
No name vintage unstructured blazer, Gant fun shirt.

Winter simply means heavier textures and warmer cloths. With looser jeans like these, I find myself wearing long johns underneath on the coldest days so I don’t spend the day shivering…
The things we do in the name of pulling off a look.

Drake’s style with Drake’s fun shirt, navy camelhair blazer and desert boots.
Rugged with vintage BB sack jacket, double denim and C&J derbies.
Double denim in the RL style, with navy blazer and cowboy boots.
With the fun shirt I designed last year.

There are plenty of ways to style faded jeans with tailoring, and I feel like I’ve barely scratched the surface. I’m at a point now where I’m hanging up my current Levis in order to size down, as they are now hanging off of me. I’ve been steadily – and inexplicably – losing weight since the start of this year.

However, when my *new* (’80s Made in Australia) pair of 505s arrives, I’ll be giving them some mileage before the sun really kicks in for summer over the next month or two. Long live the jacket and jeans.

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With content features ranging from occasional appearances on popular menswear hub social accounts (The Rake, Styleforum, Put This On) to French perfume newsletters and university course readings, Sam is an enthusiast, designer and writer in the fields of menswear and fragrance.

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