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The actual answer is: it depends on YOUR wardrobe.
Ok, assuming I like how a certain hat looks in both colors, is brown or gray easier to match?
My overcoat is black. I have black pants and gray pants. I have brown shoes and black shoes. My gloves are black. I own shirts in gray, black, white but I don't own any brown shirts.
I think gray goes with more colors.
Bottom line, get the hat you imagine yourself wearing more.
.. A gray hat might suit a 30 year old businessman better while the brown hat might suit a 20year old college student, even if they both dressed similarly?
Well I'm at the point where I'm so new to it, hence I'm not sure which I'll actually wear more. I like how both look, and I can't really decide; both are classic colors, otherwise if one was hideous or a really unorthodox color, it would be an easy decision. The reason why I'm hesitant to get both is because I'm already getting a black one (different hat), so I'm going to end up with 3.
Also, is age a factor? E.g.; A gray hat might suit a 30 year old businessman better while the brown hat might suit a 20year old college student, even if they both dressed similarly?
If you decide you made a wrong decision, chalk it up to life and get on with it We ALL make these at times.
Ah well, I guess i'll just have to learn from mistakes then.
Go for it We ALL do Enjoy 'em and pay attention as you do and a LOT of questions you have had will sort of answer themselves. Looking forward to seeing what you buy
The same way you wouldn't wear certain garments of clothing together to avoid clashing. I have to ask this because I don't always wear monotone. The other day when I tried on the hats at the boutique was an exception (I was garbed in black from head to toe).