Suzanne from my webcomic Off-Stage has been wearing the same outfit as when the comic started, as have her co-stars for the most part. Having a single well-designed and recognizeable outfit is great and works for many comic characters – but Suze’s could have used a few more iterations. So I wrote a subplot where she changes her appearance a little, and went in search of a better outfit.
The two big issues I had were with her hair (that fringe was always hard to draw from different angles) and her shirt was tough to get right; sometimes it accentuated her form in a way a loose-fitting garment like that could not, but to draw it realistically would turn her into a square blob. So besides the hair I also updated her wardrobe. I tried a few things but eventually stayed closed to the original, which felt like the best match visually and with her personality (far left is the original, the NEW YORK shirt is the chosen design).