I wear good sneakers or comfy work boots 99% of my life, and I never think about my feet. However, I still end up playing 10-15 weddings a year (not to mention ones I have to attend), and during them, I feel like I'm walking on a pair of broomsticks taped to my feet. I'll totally buck up for a rad pair of shoes, but whose? I weigh 240lbs (and climbing), and although the odds are stacked against bigger in-shape guys when it comes to formal clothing, I feel there has to be someone making a comfy dress shoe somewhere. Ideally, it would be a New Balance shoe stuffed inside a leather shell. I've been through 3 different pairs and have done a couple different Dr. Scholl's trim-to-fit inserts, and none really seem to work. Halp?

 

check out dunhams, owned by new balance i believe.
i was just looking at these for a work shoe.

 

Most comfortable dress shoes I ever owned were bought from a work wear outlet and felt just like my work boots only a hell of a lot lighter..
I guess they are made for people on factory floors that don't need the safety part but for walking on concrete all day.. I still have them and don't mind wearing them at all.
They kind of look like Doc Martins but are comfortable as hell.

 

Truth. Go to a New Balance store.

 

stop taping broom sticks to your feet?

 

I have been super happy with these. Wear them everyday at work and they just feel like wearing sneaks. The only thing is the bottom is real soft rubber and smooth. If you hit some water they're slicker than owl shit.

http://www.zappos.com/hush-puppies-integrate-tan-leather

 

Nunn Bush

 

I have a pair of Kenneth Cole dress shoes that are pretty comfortable. I just wear a pair of ankle socks under my dress socks and I'm good.

If I am going to be moving a lot though I wear a pair of sketcher slip ons. they look nice enough to wear with a suit and they're comfortable as hell.

 

Echos bar none

 

Cole Haan.

 

i wear riding boots
rm williams stuff
100% leather, 100 % re buildable
very, very comfortable

 

I do love my Ecco's

 

Allen Edmonds

 

What kind of foot do you have?
are you neutral, are you over or underpronated?
wide foot? narrow?
what I'm trying to say is...no matter what everyone else says, only you will know which shoe fits and feels best.
great suggestions from folks, HOWEVER..if someone has a wide foot and yours is narrow "X" brand wont be so comfy to you
...etc

 

Yeah but the majority of the brands that were listed make both narrow, wide, under and over pronate supportive shoes...

Understandable that everyone has a different foot, but its not like these guys make one shoe

 

Eccos are great shoes. Soles are super durable, not to hard either.

 

Good choice, I've done Clarks, Bostonians, Nunn Bushes, and Bornes. All good shoes. You have to find the right one. Since you're in the area go to the Clarks Store in Naperville. They'll pull down half the shoes in the store in your size if that's what it takes. The best bet is just to keep trying on shoes until you find ones that fit right. IMO that's super subjective.

 

Yup... gotta try a bunch to see what you like... Just like handguns!

 

I rock the Nuns Bush too.

 

I always used to wear Florsheim dress shoes and they were comfortable.

http://www.florsheim.com/shop/index.html?gclid=COq757Lf36wCFYXrKgod80ccoA