Thanks so much, Angie! I thought you'd forgotten! Now I see what you have in mind! These are definitely cute styles. I like the length a lot, and the curl. I think #1 is my favorite; she has a higher forehead than most, which also helps with visualizing how it would look on me. It's also giving me good ideas for the bangs/fringe.
I've always had a hard time visualizing what hairstyles would work for me. My face is very much not a "classical" type beauty shape; it's hard to even categorize.
It's kind of a long rectangle, square-jawed from the front, except the chin keeps on going. What consistently looks good is softness and width around the face, and these styles deliver that. I think #2 wouldn't work; the blunt bob frames her delicate, round jaw, but
would emphasize the length and angularity of mine.
For what it's worth, the single celebrity whom I do resemble best is Jean Arthur, James Stewart's co-star in Mr. Smith Goes to Washington. I don't usually look for resemblances, but I was struck by it the first time I saw her profile, and then in multiple other photos. I've grabbed some pictures. (These are NOT hair ideas - just trying to show a similar face shape and how different styles affect it.)
#3 shows what I mean about the jawline; her hair just meets the square angle to soften it.
#4 particularly resembles me. Unfortunately it's one of her least attractive pictures! The bangs emphasize her nose (which is shorter and less prominent than mine) and chin, and the long hair by her face also adds (unnecessary) length.
#5 is another with longer hair. It frames her face more, but to me she looks older than some of the others, with a longer/squarer face.
#6 with the hat shows an overall silhouette rather similar to Angie's #1, 4, and 5, with the line of the brim mimicking the longer fringe in those photos.
I don't have many non-WIW, non-costume pictures of me handy. These show different angles:
#7 almost straight on, from a slightly higher angle. My face is longer between eyes and mouth than is typical; the forehead is also high. That's the primary reason I've worn a fringe all my life.
#8 is further back than profile. Roman nose, good view of the length of my face and jaw.
So... I THINK this sort of thing (Angie's pics) would work. The biggest trick is the length and location of the fringe. I think a shorter one is best, like in her #1, because it can curl/flip/add width to the side of my face. The part is not very far off center, either, just over her eye.
I would have trouble with #3 and #6, since I have a very low tolerance for hair touching my face or obscuring my vision. Poison eye? Poison feel? I've come a long way that now I can let my hair cover my ears. I used to not do that!