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Home arrow ASK THE GUYS arrow I'm just wondering what you guys think of pointy-toed shoes for men?
I'm just wondering what you guys think of pointy-toed shoes for men? Print it Out: you can keep it handy Pass it On: send this article to a friend
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This question’s from Steve, looking to get a bit more hip . . .
Q: I'm just wondering what you guys think of pointy-toed shoes for men. I like the look, but I'm not sure if they are right for me, I'm around 5'10", so kinda on the short side. Would they make me look weird?  Also, if you think they are a good thing, which brands would have the best options.

Thanks, Steve


A: Steve, Brian here. You mean the roach-killers? I remember wearing creepers and similar styles back in the day and I was pleasantly surprised to see the look making a comeback. In general, I like them, but recognize that they are only for the hip and hip at heart. You need a wardrobe and attitude to match them. My partner-in-crime David says pointy toes for men should be in cowboy boots only.

I don't think you're height is a problem, but your shoe size might be. If you have big feet for your height, it'll be noticeable. I wear a size 13, but I'm also 6' 2". The real issue is that the slim silhouette and skinny tip makes for a narrow toe box (the space where the ball of your foot and toes sit in your shoes). Assuming you're a medium width, you might need to go up 1/2 size for comfort, which means the shoes will be longer-looking. Dolce & Gabanna does several versions, as do Kenneth Cole, Donald J Pliner, and Salvatore Ferragamo. I've owned several Kenneth Cole shoes and find them comfortable, plus they have my size.

Since they are sleek, whatever you're wearing needs to match them. No baggy jeans or slouchy khakis. Lean styles, like the Christian Dior Homme stuff by Hedi Slimane, D Squared, Lucky Brand, -- basic rock-star gear -- work best. Slim jeans (like Levi's), t-shirts, fitted shirts, and trim jackets (blazers, short-waist jackets), and clothes from stores like Sisley work well, too. The clothes will impact how good the shoes look.

Finally, I might suggest blunt-toed shoes as an alternative. I have two pair, both brown. One pair are suede ankle boots from To Boot New York by Adam Derrick; the other, split-toe oxfords from Melzan. Both have that long line of the pointy toes, but are slightly blunted at the toe. They are hip, yet still wearable with most of your day-to-day gear.

I hope this helps.


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< Go back, check out the previous article
5 Ways to Be a Better Guy
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  • The "morning after" breakfast - fresh coffee, some eggs, decent bread, fresh fruit.  And some Al Green.
  • Yes, she’ll catch you staring at her.
  • Take your suit to the cleaners only if you get a serious stain. Instead, clean small stains by hand and hang it outside to air out.
  • Cell phones off every time you step into a meeting, movie theater, or restaurant.
  • All underpants with holes are no longer clothes and are now rags. 
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Good Stuff for Better Guys
Cocktail Shaker
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Be Better Guys: Cocktail shakerIf you're mixing cocktails – the key word being cocktails – you'll need a cocktail shaker. Stainless steel is more forgiving than glass or plastic and looks good. Now, offer her something besides Chex Mix. Available at Crate and Barrel and other stores.
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