Wanted: comfortable walking shoes

I'm currently obsessed in searching for a comfortable (and fashionable) walking shoes for our upcoming NY trip. I only have a 5 year old New Balance rubber shoes that served me well during most of our trips, local and foreign. But I want to try something new and look fashionable this time. I want a mary jane-type of shoes that goes well with skinny jeans, and I think my New Balance will not go well with my skinny jeans. (arte!)

 

I recently bought a Fila mary jane-type rubber shoes during the MOA sale (P1,500) and I thought it would be a good walking shoes since when I tried it on (walked back and forth), it felt comfortable. It also looked cute and could be paired with any type of outfit. However, after two weeks of breaking it in, I noticed that my little toe on my right foot feels sore after a long walk (I thought breaking in a new pair of shoes would loosen it up?!). It seems like my little toe grew big or the shoe shrank. Oh well.

I really don't want to spend anymore because I already used up my budget for shoes (I only buy rubber shoes every five years). But I don't want to spoil our NY vacation by wearing uncomforable walking shoes. Haay.

I tried this:

this:

and this:

this too:

and the winner is:

I hope I made the right choice. I'll be wearing this to work everyday to break it in.