I used an Oceanic OceanVu mask for all my pool and OW dives. Kept leaking on me, and got really bad during an OW dive where I was doing uw nav. Clearing mask took precedence over everything else.

Went back to the LDS and got two more masks to try, with shorter skirts this time - Oceanic Shadow and a Hog. Shadow kept leaking on me during my dives at Gilboa last weekend. Will try the Hog this weekend

I have very deep smile lines/creases on either side of my face. Doesn't matter how loose or tight strap is. It's positioned properly towards the top of my head. I must move my face around with a reg in my mouth, because the water just keeps coming in from the bottom.

I'm tempted to get silicone grease like guys with facial hair use and put it on the bottom skirt.

Guy from the LDS who was in my OW class loaned me his mask to try.

I spend way too much time clearing my mask.

Any ideas?

ETA: shop has a very good return policy, so I can just keep trying until I find a mask that fits.

Choose a bunch of masks and try them on in this manner:

Strap folded forward over the lens, place the mask on your face and inhale through your nose. DO NOT put the strap over your head.

The mask should collapse toward your face. DON'T EXHALE THRU your nose.

Shake your head side to side; if it stays in place, nod vigorously. If it still stays in place, you have a keeper mask. If the mask doesn't collapse to your face, move to the next one, regardless of how it looks or "feels".

DON'T over-tighten the strap! Sealing on a mask is done by the skirt and facial fit, NOT by tension of the mask strap. The silicone grease trick is an attempt to mold your face to the skirt and rarely works for clean-shaven faces.

When you find a good sealing mask, adjust the strap so it just keeps the mask in place and tweak the fit after using it a few times.

Something else- go to Wal-mart or a similar store and check out their masks. A lot of times, you can find a mask their that fits really well and is dirt cheap. Just make sure the lens of the mask is marked 'tempered' before you commit to buying one. I haven't bought a mask or snorkel in a dive shop in 35 years.

I get laughed at because I dive an extremely expensive reg/comp/wing set up (compared to most recreational gear) and a $20 deep sea clarity mask.  

Most divers I know have a lot of masks they bought trying g to find the right one.

Took my very first mask back to the shop yesterday and returned it. Didn't get cash back since it was past 30 days, but I got full store credit which is fine since I'll definitely be buying other stuff.

Have the loaner and an inexpensive Hog mask to try tomorrow.

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I tried the shake head side to side with the loaner mask last night and it did stay on my face.

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My shadow mini leaked a lot on the first few dives. Every mask I've ever worn has needed to be broken into my face. I have a cheap deep-sea that took time to fit correctly also.

I got lucky. When I got back into diving I need new equipment, and firt on the list was a mask.
I decided I wanted a low profile mask and after a lot of reading decided to go with a Hollis M1 frameless. I bought it online and never tried it on until it arrived.
It fits me perfectly.

Well, the Hog frameless backup mask fits and doesn't leak...much. So I've got a backup mask. Forgot to try the loaner yesterday, but I'll try it when I dive next in a few weeks. I've got several friends who swear by the Aqualung Micromask. I'm giving it a try. DRIS is out of stock right now, but has one ordered for me.