First I should probably say this: I'm not one of those guys who can wear sweats and a bathrobe and still look great. As a matter of fact, I'm not really anything above "okay looking".
The truth is, I buy almost all of my clothes secondhand. I shop clearance racks at Target, I've never spent more than fifteen bucks for a pair of jeans, and I've never set foot inside an Abercrombie and Fitch. Honestly, I've just never seen the point in paying fifty dollars for something at the mall that I can get for five dollars at the thrift store. I'd like to think I've cultivated my own function-over-form style, and that it works for me, but lately I've been worrying that things like my 1960's army field jacket (or my "hobo jacket" as my friends call it) are hurting my chances with women.
In the spirit of full disclosure, my clothes aren't the only thing I don't spend too much time on. I don't style my hair beyond running a little water through it so it'll lay flatter after I wake up. I don't put product in it and I don't get it cut in the latest style. That's just not me.
It's not that I don't care about how I look, it's just that I don't look like everyone else. Most of the guys I hang out with shop at Buckle or at least the Gap, so my flannel shirts and hiking boots tend to stand out. And before you draw any conclusions, yes, my personal hygiene is fine.
I know you guys are going to tell me not to change my style or who I am, and I don't intend to. I'm going to keep wearing the clothes I'm wearing regardless, I would just really like to know what women think of guys who dress and look like that.
Most Helpful Girl
Who knows if an older woman's opinion will mean anything to you, but I'm going to give you mine anyway.
As always, with preferences, it depends on the individual. For some clothing is a personal expression, they dress to impress but don't hold it against everyone who doesn't follow suit. Then there are those who want to date like-minded men. If they make the investment to look good they also expect their significant other to as well.
For me, I wear what I like - I have spent and exorbitant amount of money on one item of clothing that I couldn't live without (it was a magic shirt!) and spent the same amount of money on a bag full of discount thrift store items that I love equally. I don't care where people get what they wear as long as it makes them happy. I think the message you send with your fashion practicality is more important that what you use to cover your nakedness. As a woman, I admire that you are focused on maintaining your individuality instead of changing who you are as a way to "fit in".
Take it for what it's worth - just like some women won't look at you twice because you're a brunette not a blond or because your skin color doesn't match their idea of what is attractive, you're going to find women whose eyes will slide over you with disinterest because you forgot to put your guy liner on and didn't shape your brows. It depends on what she finds attractive.
I guess your biggest obstacle is your own preferences. Are you only attracted to women who use clothing as a criteria to date? Or are you just asking because women aren't beating your door down to get a piece of you? ; )
That's just how I feel about it all - clothing, like all art, is up to interpretation. It depends on who's looking.