My hometown friend Mr. O’Brien contacted me on Facebook with a question about something I’d always taken for granted. He asked “George – I need to know exactly how jeans should drape over dress shoes…”
There are a couple of ways to answer this, depending on the person asking. In the case of Mr. O’Brien, we’re talking about an old family friend I’ve known my entire life who appreciates a more tried and true style. I prepared a 501® photo example directly from the Levi’s website for him (above). Levi’s has the smarts to show several different examples of how guys are wearing their jeans these days. In the 501® photo above, the model is styled with a very basic break over the shoe. Though the model’s shoes are casual, the same silhouette would apply to a dress shoe. The jeans’ cuff comfortably covers the top of the shoe, with a little break over the front while the back falls halfway down the back of the shoe. No ankle or sock is showing when standing.
Knowing what I know about Mr. O’B, this was the answer. If the questioner in question were of the young urban hipster variety, I’d have a very different response, in light of all the kids rolling the cuffs up lately. As cool as the rolled-up look is, it falls into the “trend” category. It has come into vogue, and it will go (and then come back again, in a skinny or roomy way, just like it has since Marlon Brando rocked the denim in The Wild One in 1953).
As I’ve written before, designers will “re-invent” men’s jeans and trends will come and go. After the dust settles, the classic Levi’s 501®s will still be standing. No one ever looked silly in them.
As far as the length? It depends, as I said, on who is wearing them. Personally, I subscribe to the same tried, true and trend-proof school as Mr. O’Brien.