The best is when you don't realize you've bought them all, over the years.
Going into queue, "Hey I think I'll play X Champion, haven't seen them in a while."
Look at skins
"What the fuck WHY DO I OWN ALL OF THESE SKINS WHEN DID I PAY FOR THESE I DON'T EVEN PLAY THIS FUCKER"

When you own all the skins for
and wonder how you're not homeless.

What 'em I doing with my life?
Shyvana Quinn Yasuo. And I wonder where my money is
Katarina..Quinn...all of the skins....please, my wallet..it's starving..
TaRic , malz and aatrox, alas I have all Kayle skin you can buy but silver and judgement will forever be out of my grasp

God I can't wait for the rework
My worst is 
I own haunting, dryad, and order of the banana. I think she is the only champ I have more than 2 skins for tho.
Every Skin shall be bought on the day of it's release!
When you don't own any skins for your main.
undertaker
pink
battleborn
angler
totemic
and SGU
good purchases, all

Of all my mains there is one that I haven't collected all the skins for. I still need to finish my rock collection! 

The hardest decision is picking how to nuke people... Firecracker machinegun, Bunny Rabbit Machinegun, The violin of doom, or the diesel motor shrapnel launcher.
Happens to me with urgot

I'm guilty in the fact that i need to have all the skins for my mains ._.
Is it just me or do those clothes look like they're covered in penises?
(not silver kayle though cause cant get)
wtf am I doing.
I have this strange habit of buying a skin for my favorite champions and then getting bored of it rather quickly, making me buy yet another skin and ending up with cycling between all of them.

(except vic ;_;)
(I guess)

One-off's include
(inc. vic and pax)
(too bad the slayer/demon skins both sucked)
(blood moon sale where)

Too fuckin' many skins (most bought on sale at least)
I thought I mostly had bullshit skins until last year when I looked up some of my skins. Turns out I've got UFO Corki, Silver Kayle, Judgement Kayle, Human Ryze and Urf Warwick. I've never even really played Corki or Kayle and Ryze fell out of favor for quite some time as well. The only skin I used was Urf Warwick. I still am a horrible Corki, Kayle or Ryze player so those skins sadly never get used :/
I own every horse in the stable
I was shocked when I played ARAM and noticed I own all of Urgots skin! I'm pretty sure I bought battlecast, the others I'm pretty sure I got through mystery gift!
: Which malphite skin should I use? I have them all.
: What skins are there?
: Mecha, Ironside, Glacial
: Go Shamrock
: ...
Every single game it feels like I ask which skin should I use and people respond with Shamrock. Shamrock Malphite is booger Malphite. Its his worst skin :(
+1 for zoolander*[slayer-jinx-wink]*

All skins plus chroma pack... and I usually think "just buy the best skin they have."
Hwhoops.
I have every
skin. I play her a ton too.
But i suck at Jungle. Whoops.
_midalee for the win i guess _