Most uncomfortable shoes you ever owned

[kickvicisous]

Going through the closet and found some old Flightposites from the mid 2000's, put them on and realized why they were at the bottom of my closet and why I didn't wear them anymore. Flightposites look great but they hurt ALOT (for me atleast), ended up selling them because of this but it got me wondering has anyone else tried to keep and rock a pair kicks that looked great even though they were uncomfortable.

 

[andretti]

Jordan 9s.

 

[kickvicisous]

Jordan 9s.

Never heard anybody bring that shoe up, I wore a pair of 9s on night out DC and they started to hurt bit but that was after like 5+ hours of walking and bar hopping

 

[SC kid]

These

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The first retro.

Not sure how the new ones feel

 

[dtb00201]

Cdp 11

 

[kickvicisous]

These




The first retro.

Not sure how the new ones feel

You lost me on this one, the Pippen 1 is one of my favorite sneakers ever and for me are incredibly comfortable. I wore the first retro of those into the dirt and grabbed the latest pair that dropped on sale

 

[Maximus Meridius]

Jordan 7's. They had that lil cushion around the ankle and that's it.

 

[sfc415]

All the Jordans I bought between 2003 and 2007. Can't believe I used to wear those ugly cardboard insole and plastic "leather" shoes

 

[nazdrowie]

Hyperflights, and 9's for me...

 

[kickvicisous]

All the Jordans I bought between 2003 and 2007. Can't believe I used to wear those ugly cardboard insole and plastic "leather" shoes

Funny you say that because alot of people (mostly older heads) feel those were the best years quality wise for alot of Jordans. I only own 4 pairs from that era and I have no complaints 

 

[bendover]

Adidas shell toes.
I'm flat footed. Don't know if that matters lol

 

[6 Rings G.O.A.T.]

I didn't owned these but I played basketball in Chuck Taylor before..

 

[lamekilla]

2011 Concords.

Kenneth Cole wingtips.

 

[you go boy]

2009 space jams :x

 

[nazdrowie]

Kenneth Cole wingtips.

once i switched over to square toes, everything went right...

 

[servechilled81]

AF1, might as well be wearing cement blocks, my feet would be on fire after school

 

[Arthur Shelby]

2009 Space Jam Air Jordan 11

 

[6 Rings G.O.A.T.]

2009 space jams :x

2009 Space Jam Air Jordan 11

I think that's the winner.. I feel like I had to break my toes to fit in the shoe..

 

[Nereyda Vuelve Por Dios]

Boat shoes with no socks preppy style. Killed my Achilles with scratches and blood. Never again. Better options for when occasions call for those kinds of shoes.

 

[SC kid]

once i switched over to square toes, everything went right...

went hella right



right angled


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[flacobey]

Foamposites are pretty uncomfortable to me now. I use to wear them all time.

 

[Peep Game]

These Bike's running shoes my dad bought my 8th grade year in 99/00. They were so garbage, I remember one of the bubble's burst on a distance run and after awhile, it looked like somebody took sandpaper and filed the soles off

 

[youngthundercat]

once i switched over to square toes, everything went right...

went hella right



right angled


View media item 2282459

 

[2Sky0waY6]

All the Jordans I bought between 2003 and 2007. Can't believe I used to wear those ugly cardboard insole and plastic "leather" shoes

I feel you on that. I stop buying when I got the fire red 3's so damn pissed almost threw it away from that fake plastic ish they got going on smh.

 

[og_Rodney]

These. I can usually wear just about any pair of sneakers, but I've never put on a shoe that hurt so bad that it enraged me until this pair. I ended up giving them away, **** everything about that shoe.