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Location: NYC based - Used to Live in Philly - Transplant from Miami
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You can do both.
If you don't wear socks, make sure that your pants are hemmed a little bit shorter so that it shows your ankles as you walk. But also make sure that your pants are either skinny or slim fit. If the pants are baggy then you look like a clown.
If you wear socks, you can pair the shoes with funky color socks just like the ones u can find in Happy Socks.
I wear mine without sock usually. But I have one from Cole Haan that requires me not only wearing socks but also pad because my feet will blister and bleed. (It got to the points that on the back of shoes you will see red marks from blood). Steve Madden and Allen Edmonds are usually easy to wear without socks.
You cannot blame him. Older generatio; especially in rural areas, have different views of certain things. My dad said the same things; that I look low class with my loafers sans socks.
Not wearing socks is gross, but wearing socks looks odd.
How about wearing the no-show socks? Where's that option in the poll
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