Random questions to which you seek an answer
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I don't own the 555 so just hazarding a guess but I would bet the 555 are a little slimmer in the top block than the 301. The 301 is tapered from both the inseam and outseam so it's a very tapered cut, the 555 is a very slim straight cut, it is straight at the outseam allowing for exposed selvedge edge at the leg opening
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Quick note on the brown/black thing: Yes, you can mix them. It used to be one of those 'rules', like not wearing white after Labour Day. However, if you aren't comfortable doing it, then don't.
I wear black leather winter gloves with brown boots and feel okay about it, but I'm not sure I could mix boots and belt.
And my watches all have black leather straps and I wear those with brown, too.
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Yeah, there used to be rules such as "don't wear black and blue", "no brown pants with black shoes". It all boils down to how comfortable you are wearing them. I tried to match my belt with my shoes in a business/office setting. Other than that, I pretty much wear whatever I want.
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^ I wouldn't mix black and brown leather when wearing a suit but in casual, I don't think it matters. I wear black leather Red Wings and a natural leather IH belt.
What really makes me cringe is seeing brown leather dress shoes with a grey suit