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The preppy look doesn't strike me as gay but just ultra-conservative... kind of too old for a guy in his 20s or even 30s. T-shirts and sloppy jeans or running shoes doesn't look stylish, though, either.
Maybe try to make your look a little more urban... regular shoes instead of deck shoes, trendier belts instead of the preppy belts, more casual buttoned cotton shirts instead of the polo shirts. Get away from sporty clothes and go for an urban look.
But at my university almost every single guy dresses like that. It's normal for Greek males to dress like that. Vineyard Vines, Southern Tide, Brooks Brothers, Patagonia etc.
I don't like the pink chubbies though. Something about the color is sooo ugly about them yet every guy insists on wearing them.
So, I am 20 years old and I been trying to dress good by wearing oxford shirts and polos with boat shoes or driving moccasins with matching belt always. The problem is people keep calling me gay when I have switched to this style and I don't really live in a wealthy area. So do girls like it when you dress well or more casual with t shirts and running shoes? That way girls and guys don't think your gay. Like in my area guys wear jordans or running shoes and try to match shirt with shoes. Even though, that looks odd.
Those outfits (except for those blue pants!! ) look like they could be in my son's closet. It looks fine to me. Girls love him...never been accused of being gay that is for sure. LOL.
# 4 looks fine for a bunch of guys hanging out in business casual clothes after work.
Then again, I have been called gay for wearing skinny jeans in winter.
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