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You may want a more relaxed fit but does it reflect a sloppy appearances? Jeans and sneakers don't go along. It's very.. un-stylish. if you want to attract, you have to be well groomed and well dressed. if you want to dress like that, you should go to a beach.
I don't know. I never feel like i look sloppy.
That's cause you're used to it. Used to dressing that way. I used to think i dressed well, till i realized that things just didn't match. It's not really what you think, but what others think. Isn't it?
Do not ever listen to advice like this, I haven't posted for a while but this needed to be addressed.
I've read a few post's about how you should dress for other people - the end of this road leads to caring what people think which is a quick way to being unhappy.
Just be completely comfortable with what you wear and make sure you carry it off. Clothes should be a reflection as you as a person.
In my late teens I consistently slept with women in their later twenties wearing exactly what you described in you're post, jeans, t-shirts and air force one's. People on this site who have been out with me can confirm that these weren't just 5's or 6's we're talking 8's and above.
The best example I can think of is Russell Brand, do you think he dresses for other people or buys EXACTLY what he wants to wear regardless of what everyone else thinks.