I always ended up with the infamous raccoon eyes and finally switched brands and I've been very happy with my new one. It's L'Oreal Double Extend Beauty Tubes and I buy it at the drugstore. It has 2 applications, but I don't bother with the base coat, I just use the black side. When I take it off at night I have to use mascara remover, or Almay Eye makeup remover and it takes several swipes to get it all off. If you look carefully you can see that it's little tubes.

One tip that may help is to remove excess mascara from the applicator before application. You can always apply a second coat.

http://www.lorealparisusa.com/en/products/makeup/eye/mascara/double-extend-beauty-tubes.aspx?shade=black

What products are you using before hand? Are you adding a moisturizer that may have oils in them causing the mascara to fail? Also, try to be aware and see if you are unconsciously touching or rubbing your eyes at all. Or if you have any tearing. One day I went for an afternoon walk and the chill in the air and the breeze caused my eyes to tear and I came back a mess.

I've used the l'oreal tube stuff maire-cate mentioned and it does stay put.

I do the same thing. It makes a softer, more subtle line and no smudging.

I line my eyes with shadow also. I use a small, stiff, slanted brush that is used for lining the eye. It really gives a lovely look, not at all harsh like an eyeliner can look.

I just tried a tubing mascara from Estee Lauder and I love it. I have absolutely zero smudging or flaking with it.

Using eye cream in the morning makes my eye make up migrate. The Loreal mascara mentioned above does not smudge or flake on me. I only wear eyeliner on my top lid.

You need eye base and primer to start, and powder to set. I, like you, typically look like a raccoon in no time at all. But, I found Trish McEvoy and finally can feel confident about my eye makeup.

I use her tube mascara and liquid eye/lash liner. I NEVER thought I'd be able to use a liquid liner, although I love the look. This stuff is easy to put on, even for an unsteady hand like me.

http://www.trishmcevoy.com/p-584-lash-enhancing-liquid-liner-pen.aspx

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I swear by Trish.

I was going to suggest being careful with your eye moisturizer also.

I recently tried the L'Oreal tube mascara. Didn't like it. I've tried it for 3 separate days. First day tried it with the base coat. Took too long to apply IMO. Second and 3rd day didn't use the base coat and couldn't tell the difference. It was cheap so I was willing to try it just to see what the hype was all about. It clumped badly on my lashes and flaked quite a bit. I am back to my Bobbi Brown.

I have extremely oily eyelids and cannot make my shadow or liner last on top all day. I do line below and it has a little more staying power, especially when I line with a pencil and they go over it with a bit of eyeshadow. This also helps to tone down the liner a bit.

I tried the Urban Decay primer that was recommended here for lids, and it does not work on me. If anything, it seems to exacerbate the problem and makes my shadow and liner crease first and then slide right off. I wanted to love it, but I hate it. :-(

TQ, for your eye lids, try Benefit Stay don't Stray.

Oh, darn, TR...I was all excited to try the UD primer:( I've wondered if eye lid primer isn't just one more product being pushed which may be unnecessary. I enjoy Dominique Sachse's youtube videos and she uses her foundation as primer, says she doesn't see the need for dedicated eye primer.

TurquoiseRose, I suffered from the same problem and when Bobbi Brown came out with the Long Wear Eye Base I was skeptical, but it truly works. I wear the medium shade and I can sometimes just wear it alone.

I just purchased a Nars eye primer and it's worthless. I wanted to try the Tarte eye primer that the Hot n Flashy girl recommended but my Sephora apparently doesn't stock Tarte products.

I've tried every mascara it seems. I've found this Clinique mascara to be the only one that doesn't smudge on me. And, this Bobbi Brown gel liner to be the only one to stay on, too. A makeup artist in Sephora got me to try the BB gel liner, applied with a brush. I thought it would be difficult, but it's easier than anything else I've used. I also wear the Bobbi Brown cream shadow.

I would think that if eye makeup is always flaking and smudging, that you are probably starting with an eye that isn't ready for makeup. Maybe you have some oil or moisturizer on your face. You should first put a setting powder on your eye to make sure it's not oily. I always start with a concealer above and below my eye and then set it with translucent loose powder, then I apply the eyeshadow, the liner and then mascara. I never have any flaking or smudging at all.

Thank you all for the product recommendations! I've been trying to be prep my eye more lately with basic powders, wiping off excess mascara before applying, etc. and it is helping. Still not perfect but a good improvement. So, I think with the addition of the products you have recommended I will get there! And it also made me realize that an oily eye won't be helped (necessarily) by something waterproof as they are two different issues.

Here's how you have to think about it, oil removes waterproof mascara. Like any form of oil; olive oil, coconut oil, jojoba oil etc are all effective waterproof mascara removers. The same is also true with your face oils. That is why the wp mascara isn't staying on. It may be waterproof, but it is not oil proof.

Are you removing your eye makeup at night before bed? I do, then also wash my face in the shower in the morning, and between the two, there is no mascara or oily residue leftover from the remover. I feel for you, I have oily AND hooded eyelids, which makes eye makeup difficult.

I've been using powder on my eyelashes for as long as I can remember, for the very reason of keeping racoon eyes away. Have also used my lightest ivory color powder eye shadow~ they both work since both are powder. The powder also helps give lashes more length.

Merle Norman makes the best mascara that I have ever used. It stays on for hrs with no smearing, etc. The key is that you have to use Merle Norman mascara primer before the mascara. Both together are about $30.00. A little pricey for me, but totally worth it, for no black eyes, embarrassment,etc.

Tats are in vogue! Go get your eyeliner tattooed on. I did it about 30 years ago and I love it! Doesn't solve your mascara problem, but you always look great! Even after a funeral or a swim.

I do the powder shadow thing for daily wear as well. Mascara is only for special occasions. I have a grey-blue & a chocolate brown (dark blue eyes here) & sometimes I mix them together. I also put a bit of powder concealer/pore minimizer under my eyes & on my outer lids first, using my finger, to fill in the 'cracks'. & I do check myself in a mirror every so often & use my finger to smooth any furrows that appear.