Should it Stay Monday: Shoe Edition

Everyone keeps recommending skirts with my Should it Stay Monday posts. I love skirts. I have lots of skirts, because I love to buy them. I think they’re comfortable and pretty. But what SHOES do you wear with these skirts? I have crappy feet and can’t wear any kind of heel for more than a couple hours. Even thin flats make me ache all over by the end of the day.

I have two main pairs of work shoes, two pairs of tennis shoes, two pairs of boots (discussed here on Style All Over, in case you want to read more of my shoe history), and one pretty pretty pair of flats. I also have a few assorted heels, cheap flats, and sandals for when I absolutely need them (like wearing heels to a wedding), but I don’t care about fashion enough to put my feet through wearing them every day.

Shoes #1: the uglies

Look, I know these shoes are ugly. But Born shoes have proven to be the BEST for me. I tried to find prettier ones, but there aren’t a lot of options and I don’t care enough. They may be ugly, but they get the job done and I’m not going shoe shopping again. It’s torture.


Shoes #2: the decent work shoes

I personally don’t think these are as ugly as the black. They’re not pretty shoes, but they work fine for days when brown shoes are called for.

Boots #1 and #2: my loves

Discussed on Style All Over. Cliffs notes: Also Born. 

I pretty much alternated them all last winter. I love these boots. They are SO comfortable and look great with everything.


Flats #1 (and only): my precious

I think these are gorgeous. I love them so. I can usually make it through a day in them, but not two in a row. I wish I had unlimited dollars to buy a bunch more pairs of Born flats. (I seem to be extremely brand loyal. I’ve tried others, I swear. Shoes of all brands, styles, and price points. They haven’t worked out.)
So, I suppose this isn’t so much a voting thing as a cry for help. One of my biggest wardrobe hurtles is finding shoes that work with any given outfit. What staples am I missing (black flats, maybe? anything else?)* What should I buy first? Are there comfortable options I’m not aware of?** Do I just need to let my feet suffer for fashion?***
*I do have brown heels and black heels I like (and neither of them are Borns!). They hurt, but the least of any heels I’ve tried/owned. I can wear them for a few hours, but take them off the second I can and don’t consider them part of my day-to-day options. 
**I’ve tried Danskos, which are supposed to be good for people with bad feet, but I didn’t like them. Should I try again?
***Even in Borns, I stay away from anything with a heel, including wedges and the like. So, tell me: do I need to suck it up and wear them? Or is there another option?

Comments

  1. I have a pair of dr scholls flats that I got at dsw. They are comfy for all day. Not too pricey. Also Clark’s are pretty comfy and have some decent styles. I love comfortable shoes.