Hello,
I figured this would be the best forum to put this question in - I am struggling to find sunglasses that will stay on my face while riding.
It has never been something I have bothered with, because the only ones that will actually stay on my face through trotting, cantering and jumping end up squeezing my head so much that I get a headache…
Anyways - what has worked for you?
Find a pair that had flexible curved temple tips.
Oakleys. They have a rubberized nose piece and side pieces. Do not slip at all. Look for the ones tailored for sport vs fashion.
This is a useful article.
I wear prescription glasses and have no problems with them slipping. For outdoor wear I have the kind that go dark in the sun, clear indoors.
I think that prescription glasses have better quality better fitted frames than most off the rack sunglasses. You might want to go to an optician shop and ask about fitting in the more higher priced sunglass range or if you are a hard fit, have a pair made in prescription frames. That is getting pricey but guaranteed less than my indoor graduated trifocals with glare reduction 
so my sense of reality on eyeglass costs is a bit skewed.
I wear Oakley’s. Expensive, yes. But they stay on. My problem is I have to buy the “quarter jacket” model, which is a kids frame.
The adult sized half jackets or really any adult sized sunglasses end up hurting my ears because of where the arms rest.
SillyHorse has the right answer. I wear prescription with the photo grey (newer ones are fast changing and dark) with curved temples. It does leave you out of 75% of the glasses markets and only a smaller percentage are available with them. The comfortable ones are rubber covered but the ones I like are metal wire. Simple enough – a lot of place on the Web sell rubber cover that slide on – not always fun to get on, but worth it. You can get bucked off and roll three times and break or lose pretty much anything except those glasses will be right there. I think people that are happy without these either don’t ride when it is hot and they are sweaty or they can take a tight fit. Mine are lose because they don’t depend on tightness to stay on. It does take a few weeks to get used to having the temple pieces wrap you ears and you have to sort of bend them about (that is why they are wire) to fit … once done … they are great. I have three sets of the same frames with the temples and just change them around as I get new prescriptions … so they are mostly 30+ year old frames. And I don’t recommend getting bucked off to test them. My wife does dressage and her glasses always slipped and I finally talked her into a pair. She loves them. Putting your hand up to push your glasses back up is not a smooth move in dressage. And she had Oakleys, straps, special add-ons, etc. Only the wire wraps work well, those glasses will go no place.
My One K helmet has pull down sunglasses. It’s really comfy
When all else fails, glacier glasses (find 'em at climbing stores/REI) WILL stay on.
Has anyone used something like this (retention band that goes around the back of your head)?
There’s a band d like this that I use for fishing…I think the brand is Froggies
Anything made for running would probably work just fine. I usually just get my glasses at the drug store but I make sure they are the kind that stick. I’ve had expensive sunglasses and they are nice but I prefer to spend at or below $20.00.
never had a problem. My Helmet is a Tippary Sprtage and i can wear most sunglasses without a problem.
I love my Oakley’s! I have “Full jacket” frames with “Prizm Road Lenses” that are pinkish in color. I got them because they increase contrast when I’m in the woods on trail rides so I can easily spot the trail up ahead and any potential hazards, but they also provide enough protection agains bright summer sun when I’m in the outdoor ring or riding in a field. They don’t slip like my old cheap drug store sunglasses did thanks to the rubberized wrap around style.
Those Oakley prizm lenses look awesome. I’m getting them!
Maui Jims are great, but $$$, so my current pair is Costa brand from Sierra Trading Post. A rimless design with polycarbonate lenses will be lightweight, which reduces the amount they have to hug your temples to stay in place. I run, and ride in my glasses and they always stay in place and don’t interfere with my helmet.
I have the One K helmet with the sunglasses and love it! Unfortunately, they no longer make them. 
Maui Jims. Try the kind called lighthouse. They are lightweight and flexible and you don’t even know they are on.
I lucked into a no-name pair for $5 at a motorcycle shop. I have a small face and most glasses are just too big for me. These not only fit under my full motorcycle helmet, they stay on well enough to wear riding! I can’t wait to get back to the shop to get a second pair so I can leave one at the barn.
I have an inexpensive pair of Stihl brand sunglasses. They are also actually safety glasses for running a chainsaw. They are light, flexible, rubber- earpieces and hug gently. They don’t fall off and they don’t irritate or hurt.
Fifteen bucks.
They will stay on my hat, above the visor on my ball cap or on the crown of my straw cowboy hat when I don’t need them. Best fifteen bucks I ever spent.
I see this as a good guide. Check it out. http://www.velvetrider.com/sunglasses-for-equestrians/#.WS6CsJKGPZ4
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