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Doesn't Obama do a diluted version of this, on a similar basis?omega4, Welcome to Styleforum.
Not much I can add at this point but to answer your querey about purchasing multiples; there are those who do this for what ever the reason, be it fit, comfort or preference.
The famous physicist Albert Einstein had duplicates of his shirts, jackets, ties, pants & shoes. He did this so he would not waste time to what he would wear next but just grab the next one on the rack. This would allow him to focus on his work.
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Doesn't Obama do a diluted version of this, on a similar basis?
I always thought a Chesterfield had a fly front and contrast velvet collar.
Anyway to your point, the clue's in the name - a top coat is supposed to go over a suit or jacket.
The suedeheads used to wear fitted Crombie style coats over a Ben Sherman. If your budget allows, why not get say a midnight blue overcoat (vertical pockets to put your hands in) to go over a suit in very cold weather, and a lighter weight herringbone Chesterfield with fitted waist and flapped pockets to go over a shirt in milder weather?