First things first, start with rugged! Choose from your ripped and worn out jeans and a shirt you may have cut the sleeves, side-boob or midriff off of. Midriff is great to add to this look, giving it a femine look without trying too hard. You can also do an oversized flannel!
Next, grab a hat! Ballcaps preferrably, just because they scream 'chill day'. you can also use a shaver, razor or knife to give your hat a distressed look.
Shoes? Uggs and flipfops! They're cute and girly but perfect the look!
Lastly, don't forget face! Yes, you can wear make-up with this look! However, ditch the bright colors! Do a natural look that still makes the hobo look seem polished. And don't go easy on the hair either! Add some curls for the girls and let them hang under the hat. For my naturals, try the bun with the part on the side and pull it through the back of the cap. Like they say, when your hair is hooked, you can wear anything!
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