Ocassionally i have trouble with new leather shoes, the fit may feel a bit tight in the beginning and may lead to some blisters or friction around the ankle. But after wearing them for a little while, i noticed the leather will loosen a bit, and become more lean and comfortable.
I think a hat and shades may be worn together depending on the type of hat, but your face may look a bit overcrowded. I personally prefer to wear one or the other depending on occasion or need.
I got a pair of silk pj's, not really vintage, but surely have a vintage look, the robe is short in length with clip on buttons, sort of loose, along with a pair of loose pants, very comfy material when sleeping as well as looks good when walking around.
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