I used to have some black ones when I was like five and a wore them everywhere. I think the boots might look good if paired with denim shorts and a sharp looking shirt:
The shirt kind of plays up the whole cowgirl look so it might be a bit much, but maybe the addition of a fun printed bag will liven it up:
As long as you don't add this hat:
I'm fairly certain Clint Eastwood would not put fake cowrie shells and aqua beads all over his bad ass cowboy hat.. Also, his hat would have real wear and tear.
Regardless of his manly man poncho, it is not look for everyone. This is NOT an acceptable poncho: