Lyric discussion by ATLien 

Cover art for Them Shoes lyrics by Patrick Sweany Band, The

It's about being a realist and accepting yourself for who you are; the choices and decisions you made, where you are now, all interconnected. He's obviously reminiscing about multiple relationships with women gone wrong, possibly a divorce or two, and how the aftermath didn't necessarily turn out how he'd hoped or expected it would. Sounds like he's even making references to child custody issues:

"You can see me in the evening When the weather's cool But here's a little feedback You gotta wear the shoes"

And the divorce:

"Now you can have a love life You have loved me, too You can see me in the evening When the weather's cool"

"You gotta wear those shoes" = you have to put in the time and sacrifice to deal with all the BS for things that didn't go to plan.

Life's tough but sometimes you just have to deal with the bed you've made for yourself.

My Interpretation