As an fashion accessary, wigs has always been an important part of beauty supplies for both men and women. Nowadays, there are even more variation of stylish hair wigs that anyone can have easy access to from online store incuding long/short wigs, straight curly wigs, human hair wigs/ sythetic wigs, customed wigs and so on.
What about a merkin?
I am in the same dilemma as you. But it might even be worse for me. I am a senior in high school, and I definitely don't dress as the "young kids do." I wear old fashioned clothes. But not suits and ties as the average Joe did back in the 1950's. I go for more of "The Waltons" look. I wear blue jeans, white undershirts, and flannels (tucked in). And as for footwear, depending on the day, I wear either mocassins, cowboy boots, or sneakers such as Vans. Some people give me odd looks, but I feel I look good and that's all that matters. If you feel good in what you wear, wear it.
And as for the women part, if women don't find you attractive based on what you wear of all things, they are definitely not "the one." I am very old fashioned in that I don't look for one-night stands as is popular nowadays. And I encourage it throughout my days. So as Ryan Danley already said, "To each their own," and may I add, "f*** the rest."
"Those who matter don't mind, and those who mind don't matter." ~ Dr. Seuss