Bobby pin the shit out of it to stop it moving around and, yeah, they look really weird with a lot of hairstyles.>>9446201
I wear my clothes how I think they look best and I'm not afraid to mix old and new pieces, but I'm scrupulous about accuracy if I'm going to call something oldschool. Authentic early-00s chiffon gothic pieces aside, I wouldn't tag anything with chiffon/modern shoes/tulle lace/whatever as oldschool unless you couldn't tell those details were wrong from the photo (like when black-on-black tulle lace doesn't show up from a distance). I also usually try to do at least one "period-accurate" outfit with all my oldschool pieces just to see how it looks, even if I think a piece looks better coorded in a more modern way.
I try to keep hair and make-up close to the roots but I think there's a bit of leeway about it as long as it fits the aesthetic and/or could plausibly have been worn at the time. OTT make-up usually looks very weird unless it takes heavy inspo from porcelain dolls or VK looks, but I think the more natural the make-up is the more you can get away with techniques that weren't used back then. As an example, I wouldn't ever do insta-brows with oldschool, but other recent trends like Korean straight brows work IMO because they look close enough to the natural brows you sometimes saw back then to blend in. Similarly, even though highlighter didn't even exist in the mainstream in the early 00s, I use subtle highlighter quite a lot to add freshness and dimension to my face - I think it works because it's there specifically to help fake a dewy, natural look like a bare-faced IW model for summery coords which doll-like matte foundation would look weird with (my skin's too bad to actually go without make-up).