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Well, even if you're still in that position, there are some alternatives that are a little more stylish but equally casual. The look of a low profile put-together chukka boot, with the comfort of a sneaker.
The Desert Boot has been a sartorial staple for decades, and if you opt for a pair in a darker color, they may well last you for decades to come.
I get bogged down in existential thoughts on the function clothing performs and wonder if we're all just suckers buying into advertising. Nothing screams late 90's more than chunky-soled, squared-toe dress shoes.
Sometimes skinny frames are trendy, sometimes big fat goggles are the trend. But…but…” There are a lot of style fundamentals that stay relatively consistent over time, and that's the kind of thing we try to discuss in length on Primer.I've often been frustrated and thought, “who makes these decisions?Even if other styles pop up along the way, this shape of shoe has been a standard for generations.I remember in college several years ago, it was pretty stylish to have the back side of your jean leg be all ripped up because they were long and baggy enough that you would walk on them. Or two, the profile of your shoes is slim enough that the jeans slide right over them.