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Churchill was overweight and he wasn't too bad of a dresser. If you want to see more realistic examples than on the sartoralist then checkout the styleforums thread "what are you wearing today", mentioned elsewhere. Suits work best on someone who is around 5'9". I am quite tall, which means I can look a bit goofy if I wear the wrong things, but just like with being overweight, it is possible to put together a combination that looks good.

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Suits work best on someone who is around 5'9"

Nonsense. Tall guys look great in suits. I'm 5'7" and I always feel a bit like Tatoo from Fantasy Island (The Plane! The Plane!) when I put on a suit.

Whether a suit looks good for your height just depends on the proportions of the suit compared to your body. A short guy can wear a suit just as well as a tall guy (or vice versa), if he has the right length jacket. This is because the jacket divides the body into two visual sections, the primary effect of which is to either visually shorten or lengthen the legs. Shorter guys look stubby if their jacket is too long and cuts through their thighs.

Hint: many clothes come in [S]hort, [R]egular, and [T]all length variations. It's good to figure out which one you are and buy the appropriately proportioned one, or err on the side of too long and have a tailor crop it for you.

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