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I think her best outfit was without a doubt her iconic dress + leather jacket combo from "Prophecy Girl" but that's a little predictable.
Ignoring that, I really like her outfit in the beginning of "Out of Mind, Out of Sight" when she's wearing a white v-neck top, printed skirt and long leather boots. The top really showed off SMG's great cleavage in Season 1 and she looks really cute in those scenes (her hair is hawt too). In fact, that's a pretty great episode for her overall and I love her outfit later in the episode when she's on patrol and peers in on Cordelia getting her dress fitted for May Queen.
Some of my other favourites are;
- Her entire look at the end of "Angel" when she kisses him at The Bronze. She's just total classic Buffy right there. It reminds me of my childhood.
- Her outfit at the end of "The Harvest" (that leather jacket and floral short dress)
- The flowery dress she's wearing at the end of "The Witch" when she and Amy are staring at the cheerleading trophy. She looks very Neve Campbell in that scene (her hair looks darker than usual, even)
Whenever I think of Buffy's fashion in Season 1 I think of her earthy brown hair, the giant rings she always wears on her fingers, the short dresses, and the leather jacket.
Just skimming through s1, I didn't see a lot that I remember from school (I find the computers and rare cell phone more like the 90s at my school). What they're wearing at the start of The Pack was close to normal. I personally think the 3 look their cutest (not taking in facial expressions, tones of voice, etc, just their clothes) either at the very start of the series, or early on when they first talk to Sid the Puppet in The Puppet Show, though I know I lingered there because again they look like they could actually have been at the high school I went to (without being sent home to change, though first episode Willow would've been made fun of at my high school as well).
Perhaps I should say I went to high school in the outskirts of Houston in 1997 - 99. I'm also speaking of "least likely to get sent home over or raise eyebrows among other kids." (I myself wore a hybrid mix of what I guess you'd call skater & grunge, as did many of my friends in the first year of high school, while many of my friends in my second year were generally as goth as they could get away with. However, these didn't blend in at all, nor do I recall seeing these fashions in season 1 Buffy.)
Looking through s1 this time, I really like how Buffy and Joyce have very similar hair. It really does help them to look mother-daughter.