Ask Skep: Cool Shades
"Hey Skep, I wear glasses so that I can function in the world around me, but sometimes the sun gets bright and I want to be able to wear sunglasses. What's the best option to protect my eyeballs while also preventing me from looking like a huge dork?"
—Blinded by the Light
Well Blinded, this is really the biggest conundrum for those like myself for whom natural selection has determined that making literally everything blurry and indistinguishable is a huge evolutionary advantage. The unfortunate truth is, there is no 100% clear "best" option to combine the ability to see things with the ability to not see them quite so brightly. This has not stopped mankind from trying, however, so I'm going to discuss your various options, ranking them (roughly) from least to most innovative.
Putting sunglasses on over your glasses
Sometimes, the simplest solution is also the best. Alas, that wisdom does not apply here. This is dumb, don't do this. They probably won't even fit.
Clip-on sunglasses
These would be any sort of sun-shielding front attachment you would find at your local pharmacy, and can come in multiple forms. From my experience, the most common are the "big plastic clip on the center" and the "claw grips over the sides". The first type usually has a large surface area in case you have sizable glasses, and they have a convenient flip-up-and-down action for alternating between light and shade; they are also incredibly, incredibly dorky and are generally to be avoided. The latter has little claws which grip around the frame of your glasses. The caveat here is that they need to be roughly the same size as your glasses or they won't fit; they can also be a little tricky to put on and take off—especially when you're in a hurry, which you most certainly are in today's society. Still, if these are your only options, go for the claw grip if you can unless you happen to already be a social outcast.
Made-to-fit attachments
Some pairs of glasses come with specially-made sunglass attachments that match up with the frames. These might be appropriately-sized claw grips, but sometimes more innovative approaches are used; I once had a pair that attached to my glasses with little magnetic hooks, which was pretty slick. Overall, these are a good, well-rounded option; but not only will your frames be more expensive, you're going to be greatly limited in the selection that's available to you since this is not a common extra. All I can do is shrug and wish you good luck.
Prescription sunglasses
This is my own personal preference, although there are still plenty of downsides. For one, unless you plan on just wearing sunglasses all the time (which is really just unacceptable for anybody whose professional attire isn't a solid black suit), you're essentially purchasing two pairs of prescription glasses, and you know your insurance is only going to pay for one. Likewise, this means that you have two pairs of glasses to manage. If you think there's any chance you are going to need a pair of sunglasses at some point during the day, you have to cart them around with you separately. You need to figure out what to do with your regular pair while you wear the sunglasses. God help you if you're the kind of person who misplaces their glasses when they're not actively on their face. Despite all of these negatives, however, this solution has one big positive that none of the others can match: When you're wearing sunglasses, it actually looks like you're wearing sunglasses.
Transition lenses
Ah yes, the "I don't want to have to put any thought into it" approach. These are regular glasses with lenses which are made in such a way—presumably involving some combination of a demonic bargain and arcane secrets that would drive most mortals mad—that the lenses take on a dark tint when exposed to sunlight. On paper, very cool, very convenient. But you know what isn't cool? A lack of control, which is something you are giving up if you pick this option. You are leaving the sunlight-blocking responsibility solely in the hands of your glasses. If you're shifting from light to shade, you need to endure total darkness while you wait for your glasses catch up. Outside on an overcast day? Your glasses might be annoying about it and go half-tint. Time to take an outdoor selfie for Insta? Hopefully you're fine with people not seeing your lovely eyes. Additionally, while certainly not the most awkward-looking solution on the list, at least the other clip-on options present a "bulkier" appearance commonly associated with sunglasses. You're not fooling anybody here; these are just regular glasses that scream "I stopped trying" whenever you go outside.
Switching to contacts
What are you, a quitter?