Are wingtips the male equivalent of the high heel shoe?

So, are you positing that the outter design of the shoe makes them less comfortable?

Wingtips isn´t as comfortable as sneakers, if that was your question. They are not painful to wear either, but I would not run 10 miles in them. As for the comparison to high heels, I am not very familiar with wearing high heels, so I can´t help you there. 

I feel far more comfortable in high heels, but probably not for the reasons you're discussing here.

This is a very strange thread.

No, they are not the equivalent, and they are not remotely comparable.  They should be as comfortable as any other dress shoe if they fit you properly.  If you are expecting something as comfortable as a sneaker, you are going to have to go down to a cheap foam filled dress shoe (something like a Rockport).  The wingtips are just the design in the leather upper (irrelevant to comfort), so they still come down to just being bluchers or balmorals.  Women's high heels are fashion first, function second.  Men's dress shoes change colors and designs to be fashionable while the foundation remains a functional traditional leather shoe.   

My brown shoes are more comfortable than my black shoes.

my wingtips have air max sole unit. seriously i don't buy into the leather soles for fashion's sake. its like wearing high feels. function over form any day of the weak.

Cap toes hurt more than wingtips and less than flip flops

No. If your shoes aren't comfortable after break-in get rid of them and get new ones. There are handsome dress shoes that would be very comfortable on you so why would you not wear them instead?

Is it just me, or is obvious troll obvious?

 

it's not very troll-y.

 

i wore my new wingtips (that i bought before joining here) for about 5 hours last night, and my feet were hurting.  i'm hoping they'll stretch out as they're tight on the sides.  i'd never think of asking the questions in the way op did, but hey..

I find that wingtips with a larger medallion are more comfortable than those with small medallions. So maybe that's your problem?

they dont fit right.

I don't wear leather soles just for fashion's sake. I like the feel, and don't find them at all uncomfortable.

Believe it or not, your foot did not evolve to require heavy cushioning at all times. If the muscles in your foot are healthy (though if you spend your entire life in heavily cushioned shoes designed to prevent your feet from having to use their muscles, the odds of that are not good), you should be able to walk, run and stand all day in any appropriate fitting shoe, regardless of cushioning. Trust me, I was doing some 6-8 hour stretches of canvassing during the recent election with no problems. I usually wore camp mocs, which don't have leather soles (didn't want to bang up nicer shoes) but aren't anywhere close to a sneaker either.

OP's shoes probably don't fit right or aren't as broken in as he thinks they are.