I finally got around to making my older versions of the Student Six in "Flurry Heart's Story!" They've all graduated from the School of Friendship and are now teaching there so that's why they're now labeled the "Teacher Six".
I know a lot of these don't look much like how the characters did in the timeskip during "The Last Problem", but part of the reason is cuz I already had designs in mind or already shown (like with Smolder in this pic: Dragons 10 years later). I actually liked their designs in the epilogue, but Smolder looked like she barely aged a day, she just grew a bit taller, so I like this older look better for her as it shows more of her having aged and starting to be as tall as Garble was in the show. For these designs, Sandbar and Ocellus pretty much look the same as they did in the epilogue cuz I thought they were good enough, but I guess this means there wont' be much of a difference when we get to whatever time the Last Problem took place in. That's ok though cuz I don't see too much always changing with the characters. I made Gallus a bit taller and gave him longer bangs to show a progression of age and Silverstream is a bit taller too and is growing a longer beak. Yona is bigger and has a different cape thingy (whatever they're called) but hasn't started looking quite as big or fancy as she appeared in TLP.
But in any case, these are my headcanon designs for these six about 8-10 years from now. Remember that Flurry Heart's Story is supposed to be between the time of Twilight's coronation and the time that the Last Problem took place so they still have some growing up to do. Flurry may be the main character, but she will befriend the teachers and they will all play a major role in the first story.