My continuing conflict with footwear (alternately: A love letter to my Chacos)

As I discussed in my surprisingly detailed essay on boots, I have a complicated relationship with shoes. I love them, of course, but it's hard to find the right pair. Now that spring is nearly here (fingers crossed), I've been evaluating my shoes yet again: hashed pair of Top-Siders I wear nearly every day, aging Chacos dying to be worn again, black Keds that I can't give up, a few pairs of colorful flats. I need to change things up:

Clockwise from top right: ASOS bow flip-flops, Topshop canvas tie flats, Topshop peep toe flats, Chaco Local Ecotread, Sperry Top-Sider 2-Eye, Birkenstock Bali, Topshop straw woven sandals

I tend to wear my shoes, especially my summer shoes, to the bitter end. And I have a bizarre sense of brand loyalty once I find the right pair. You'll notice this little collage contains Top-Siders, Chacos, and Birkenstocks, all of which are brands I love and own/have owned before.

Since I bought my first pair of Chacos, you'll rarely find me in anything else during the summer. I'm anti-flip-flop, but a huge proponent of Chacs: wear them with jeans, wear them with dresses, wear them hiking... Call me granola all you want, but I love my Chacos. I've had them for nearly five years, though, and as hard as it is to say goodbye, it's time for a new pair. I'm thinking of making a change from the waterproof nylon straps to the similarly designed, but nicer leather straps. But oddly, I feel a bit weird about that: shouldn't the point be that I can rinse my Chacs off with a hose after I wear them to First Dam? Am I weirded out because the leather Chacs are more grown-up? Shouldn't the citizens of Cache Valley lobby for a more creatively-named dam system? And why do shoes always seem to bring out my more thoughtful side?

Will I buy the leather Chacos? Or will I remain comfortably strapped into my beloved college student, been-through-everything pair? Stay tuned to find out.