Stack, Roll, or Slit Jeans for Boots?

Occasionally I get questions or comments about the correct style to wear jeans with boots. Until fairly recently, if anyone looked for images on the web about how how long jeans should be to wear over boots, the images would always show jeans long enough to gently stack (or fold) on the boot tops, but not so long that the jeans drag on the floor behind the heel. (So my “Wearing Cowboy Boots” tutorial has said for as long as it has been posted on my website).

Lately as the young’uns (aka “millennial generation”) have taken to wearing fashion boots, or the young’uns being marketed to by Tecovas Boots (since the owner is a millennial himself), there have been images that…

…show men’s jeans rolled up about an inch (2.5cm) as the jeans are over boots.

I dunno … I think this style choice may be okay with short boots like Thursday Boots (another millennial-created boot retailer), but in the opinion of this crusty old cowboy boot wearing man, not for cowboy boots.

That is, unless…

…a guy will not wear boots unless he rolls up the bottom of his jeans to make a fashion statement. If he has to do that, then by all means do so. Much better than wearing silly sneakers (or worse, flip-flops!)

You know, in some ways, wearing cowboy boots with jeans rolled up displays more of the boot and makes a statement, “this guy is wearing boots!” Most of us of the Baby Boom generation have not felt the need to make that statement.

And contrary to popular belief, guys do not wear jeans completely tucked into boots on a regular basis, with a few exceptions: working cowboys actually out there on a horse may wear jeans tucked into tall buckaroo boots; some bikers wear jeans tucked into tall engineer boots; and, of course, motorcops wear patrol boots over breeches. But otherwise, jeans are worn over boots.

What about some guys in certain western U.S. states who slit the bottom of their jeans to make it easier to wear over boots? That may be a very local custom in some areas, but that is not how most guys in the U.S. choose to wear jeans over boots. Why? Because jeans are made of cotton, the cotton frays rapidly with each washing. In just a few washes, jeans that have been cut open at the bottom (aka “slit jeans”) fray and begin to fall apart. The life of the jeans is significantly reduced. It is a pure matter of economics — cut the jeans and shorten their life to last just a few months. (Quite a waste of money if you ask me!)

Anyway, I still favor the look of jeans gently stacked on top of boots — even motorcycle boots. It is a classic look that goes with a classic, ever-lasting style. Not to mention that as jeans shrink in the wash over time, jeans get naturally shorter. The “less long” jeans are not quite as noticeable when worn over boots without the ends being rolled up.

The “roll-up” style of jeans over boots was popular for a time in the in 1950s — a style made popular by James Dean. Lots of young guys adopted his style of dress, including wearing engineer boots with jeans rolled up at the bottom.

These fashion trends go in and out of style. Roll ’em up, don’t… who knows (or cares) about fashion. Wearing jeans gently stacked on top of boots is an ever-lasting and good-looking fashion choice because it is practical and timeless.

Life is short: wear boots with jeans gently stacked over them. But by all means, wear boots! (So if you must roll your jeans to wear boots, do so.)

2 thoughts on “Stack, Roll, or Slit Jeans for Boots?

  1. I think greasers used to roll up also because there were fewer length options than nowadays, and people were too lazy to get them hemmed. Nowadays people who buy selvedge denim jeans also do it to show off the selvedge, imitating Dean is a bonus 😉

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