I have some brown Sperry Topsider deck shoes, and I was wondering if I could pair them with this outfit

http://www.hm.com/us/fashion/fashionstudio__fashionstudio.nhtml#/clothes&tags=[[25,27,496,231,232,337,28,29,30,31]]//{%27view%27:%27f%27,%27m%27:50,%27p%27:2,%27slot%27:[14871,15056],%27v%27:0.7,%27bg%27:544}

I heard that you should never wear boat shoes with official wear, and was wondering if this outfit is too official for boat shoes.

All answers appreciated, Thank you

I just bought a really nice pair of Sperry Top Siders and I need to break them in. I have never owned a pair of deck shoes before so my feet aren’t used to the feel, and as a result I keep getting blisters on the back of my heels. What is the best way to break them in so this doesn’t happen?

I’m looking into getting a pair of Sperry top-sider deck shoes. What do you think of them? Pros? Cons? How do you find the sizing runs?

Thanks!