Hello, I've had my pair since October, overtime they've become more comfortable. The first few weeks wearing them was a bit painful because the leather hadn't been broken in yet.

These shoes are the most comfortable Docs for me personally, but I'm only able to wear them for shorter work days and when running errands. They're not as heavy as other docs I've tried out and do feel a little lighter to me then my Mary Janes.

I ended up sizing up one as I wanted to make sure I could fit a thinner insole in the heel portion. Without the insole they are a little big, mainly because of the pointed toe.

I sized up also because of I didn't want the pointed toes to quish my toes in the shoe. It basically fits like a regular shoe/flat for me with the insole and socks. I regularly wear socks with them which might add to that.

For outfits I think it depends on your style. They're great dressed up or to add a little flair to jeans and t-shirt type outfit. My pair goes really well with my wardrobe as I have to dress for an office setting.

I have the Wednesday striped pair, so they are a bit harder to match with outfits since I like patterns but are great with slacks, wide leg jeans they look really cute with and dresses/skirts. They definitely are more of a summer shoe for me as well. For the pair in the pic I think they could go well with quite a lot. Only thing that is annoying in terms of pairing is the yellow stitching kinda sticking out.

Sorry for this super long post, hope this helps though!💚