I've never not had bangs. Ever. In all of my 32 years. I always felt that by having a high forehead, I needed bangs. In the past few years, I've gotten comfortable enough to braid them back, or swoop them to the side. Both of these styles took a lot of wearing them around the house first before I dared to wear them out in public.
cardigan: local shop
tights: joe fresh
shoes: spring shoes
I suppose all of this look goes with what I said above: wearing it around the house to get used to the look before daring to wear it out in public. Cat eyes with eyeliner, red lipstick... both took some getting used to. I always wore very subtle makeup, neutrals, just to add to my natural look and nothing to bold. Enter cat eyes and red lipstick, which practically goes hand in hand these days.