[Manque]

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Solo,

I've tried on many a shoe like those. They look great sitting on the shelf, but I get them on and naah. I really am a fashion retard. I think part of the problem is, with khakis off the rack(Dockers/Old Navy/Polo), the bottom of the pant covers half the shoe and just looks bad. So,I think of getting some good quality khakis and having them tailored, but now I am getting into the realm of high maintenance.

Anyone,

How should the pant fall over the shoe? Someone mentioned not bunching up, but I'm sure there is protocol.

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It depends on the narrowness of the bottom of the pant. Narrow, slender trousers should have less break than a fuller pant.