This is my submission for a contest being run on mlpforum for September/October 2020: "Re-imagine a pony (or other mlp creatures) as if they lived 1000 years ago and design them an outfit that would fit the period."
Now I couldn't actually imagine outfits for 1,000 years ago for ponies, so I went with 100 years ago instead (for us) and found inspiration for the 1920s with my favorite pairing, Derpy Hooves and Doctor Whooves. Someone else did a character dressing in and outfit from the 1920s, and I just love a lot of the fashion from the period and followed suit with different characters and outfits. Whether or not i win, I'm incredibly proud of this picture and have had a lot of fun drawing it over the last few days (as of posting it).















