Man Grooming Q&A: Boots and Shoes

Greg writes: “I was shopping on Gap.com last week, and I noticed that all of the models were wearing boots with their jeans and pants. I really liked how this looked, so I went off looking for a pair. First of all, do you have any recommendations? Second of all, I found these at Timberland.com. They look great, but I’ve never tried a ‘Chelsea boot’ before. I’m sure they would look good when I’m standing, but might look dorky when I’m sitting if you can see the elastic and the top of the boot. I’m not sure what kind the models in the photos are wearing, though, so I’m kinda stuck.”


Something to keep in mind whenever you’re contemplating a fashion change for yourself, like suddenly wearing boots, is whether you’ll be comfortable doing that because you want to do it yourself, and not just because you saw someone else doing it or it seems like a trend. I’m not sure those GAP models are wearing boots, they may be wearing casual leather shoes. Today a lot of shoe manufacturers create boots and shoes using the same footpad, just to cover all the bases.
Your interest in a Chelsea boot (and FYI all Chelsea boots have those elastic panels — they make taking them off and putting them on really easy, and these are a style originally popularized of the Beatles, believe it or not, so they’ve been around a while) seems muted by the idea that someone might see the elastic sides and that they’re ‘dorky.’ I’m not sure where you got the idea that elastic on boots is dorky, but the fact that you feel that way probably crosses a line for you and that means you wouldn’t wear them anyway, no matter what I said to you.
Rather than venture into an area you’re not (yet) comfortable with, I think you should probably stick with regular shoes or find some boots you have no qualms about wearing — indeed, find the kind you pull on in the morning and they make you feel better, not worse.
I think these Urban Oxfords at Banana Republic look great. European styling at half the cost. And if you’re deadset on getting a pair of boots, what about these lace-up Kenneth Coles?
By all means, don’t trust the Web to define your tastes. Go out to a shoe store and try a bunch on. Take your time and see what you like. If something catches your eye but you have some doubts it’s not entirely “you,” try them on and find out. They may suck, or they may make you smile. Comfort is also a big factor, of course, so if they look great but they feel bad, leave them for somebody else. You can’t hurt a shoe’s feelings.

August 1, 2005

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