Oakley sunglasses - paralyzed by options

Hey all.
If my nephew ever gets his act together, I will have a gift certificate (Christmas present :p) to spend at my LBS.
I've been Jonesing for a good pair of sunglasses, so I thought I'd splurge on a pair of Oakleys. My dream glasses would have photochromatic lenses (change with variable light), protect my eyes from cold, blowing wind, allow me to see on bright road rides, as well as alternating shadow/bright of mtb rides, and - most importantly - not fog in cold or steamy weather. Something I can wear during dark commutes as well as on 5 hour centuries in full sun (okay...I may be asking a bit much there).
Oh...and I wouldn't look like a dork while wearing them. :rolleyes:
A few women I know wear Oakly Half Jackets and think they are just the greatest. Honestly, tho', I think the lenses are a bit too small for my fat face. The Flak Jackets seem to be more sized for my face. At some stores today, I also tried the Radar Paths and the M-Frames. The M-frames are very customizable - with various lenses (well, I think they all have that), as well as vented lenses. DH thinks I should go with the Radars or the M-frames with 2 extra lenses. Only the Half and Flak Jackets come with the Transition (photochromatic) lenses. I think the M's and the Radars might be TOO big for me (the women's frames I tried all felt like the ear pieces were too short for me). I can fit my finger b/t the side piece and my cheek on both, yet the Flak Jackets fit pretty snugly. But I'm worried that the Flaks won't protect my eyes. But...Why would they be popular with cyclists if they didn't ...right?
So... Long winded way of asking....
What is the most important things to look for in a pair of glasses? Since I likely won't be able to take a pair out for a ride (well, maybe my LBS would)...how would I know if a pair really fit me and did the job? I have so many sunglasses for riding...and all of them are junk. How much eye coverage versus sweep around the face should I really be looking for? Is there really any one "do it all" pair of sunglasses out there?
Thoughts?
Thanks!

I don't know much about Oakley as i can only get my prescription into Rudy Project sunnies.

I would try and pick up a few differnt coloured lenses for dark, shady & sunny times. If you mtn bike, the orange lenses are great! When i leave at 5am for a ride & it's still dark (I keep my spare glasses at work so i don't have to carry lots of stuff when i ride) I have my clear lenses in my sunnies. I then have my other lenses in my ground effect pouch thingy.

First, try them on! I was coveting a pair of the Oakley Enduring (women's model) glasses. Then I tried them on--it was instantly apparent they were not for me. In this case, the glasses were just too small and flat-out uncomfortable.

I find most unisex glasses to be too big. And I also remember (granted this is a ways back they may be better now) that photochromatic lenses are not dark enough when it's sunny and too dark when it's not--the worst of both worlds.

If you do a lot of riding in a aggressive position or in the aerobars, you may want a frameless pair. I have a pair of Rudy Project Maskerynas that I like for riding.

I like to step out into the sun and compare the light that leaks in over the top, bottom and sides of the lenses. And if you like, take pics of yourself with a digital camera and post them here - we can give you feedback (if you narrow it down to comfortable and functional ones, but don't know about "the look" in them.) I second Ilima's info about the tint of the photosensitive ones - it's not the full range of very dark to very clear. I think I look weird in my Rudys, but they fit and I have my Rx in them. Tokie

I also like the Rudy Project lens. Their photochromatic is clear and go as dark as 18%. The lens says 18-78% but I find it so clear I don't know why it says 78%. I can definately bike at night with it. They also have a polarized one that is quite good. I find the Oakley M frame to be good but it doesn't have photochromatic lens, which is too bad. Try out a Rudy. You might like it better then Oakley.

I have a pair of the Flaks and I love them! I used to have a pair of Specialied glasses that were very similar in size to the Radars, and I like the smaller size of the Flaks. I do not feel I lost anything by going to a smaller frame.

I use the Flak Jackets as my daily glasses and I must say I truly love them. They are the most comfortable and lightest pair of sunglasses I've ever owned. The first pair I can honestly say when I put them on I honestly forget they're there.

With that said, I still use the Radar Path for cycling. I like the coverage of the lenses against road debris, and I feel like they fit my face well. Part of my reason also stems from the fact that I would be upset if I ever lost or damaged my flak jackets. The radars definitely don't look the best on my face, but hey I'm running around in spandex and bright colors, so I'm way over worrying about what others think about me. I never carry extra lenses with me. For bright days, I use the standard grey lens for really bright days, the G30 lens for overcast to bright days. I have really grown to love the G30, it's a great all around lens especially for cloudy days.

The whole "hydrophobic" coating issue appears to be mostly marketing to me. My glasses still pick up plenty of dirt, dust, and when the inside hit my eyelashes eventually they need to be cleaned of grease. So if that's one reason steering you toward the Radar vs. something like the M frame hybrid, save your money with the M frame if it fits you better.

One more suggestion, have your helmet with you when you try on your glasses. Some of the glasses have longer ear stems which can hit the back of your helmet and keep you from getting a solid fit.

In the end it boils down to personal preference and only you will be able to decide. Let me know if you have any more questions.

The most important things to get are UVA/UVB protection and polycarbonate lenses (or non-breakable). I assume you don't need prescription sunglasses, right? For those people who need prescription sunglasses (like me), I would recommend NOT going to your LBS for that but to an optometrist who knows sports glasses. Most to.

I love my Rx Tfosi sunglasses, but I got them through a bike shop and I really should have gone to the optometrist.

Thanks, all.
Since I have the gift certificate with my LBS, I'd get the glasses there. They carry Oakley and Tifosi (and one other I don't recall), but not Rudy Projects. I don't need a prescription (yet?!?), so that's not an issue. Good idea, Alpha_Omega, on bringing along my helmet. DH and I talked about that, but didn't really plan on looking at glasses. We were at a mall (a rare event in itself) where there is a Sunglass Hut and an Oakley store, so we thought we'd browse. I'm wavering b/t the M-Frame hybrids and the Flaks.

Take your helmet with you when you try them on!

I have a pair of the Oakley Half Jackets and the fit well for me. I actually got them from my boyfriends sister because she has such a small face/head that they didn't fit her. I like them because they have enough room on the sides that I can put them over my helmet straps. If I put them under the straps they fit different and don't feel right.

The best advice I can give has already been given. Bring your helmet and try them on. Plus, I think I look totally different wearing my glasses with my helmet than without my helmet.

I have Oakleys, Radar, I think, and they're more comfy with my helmet than without, because the spot where they rest above/behind my ears is on a plastic helmet bit, and helmetless it is just right there on the bone.

The half jackets have a larger lens option called xlj. Maybe that would work for you.