I have always had high contrast colouring, and I sort of expected I would need to switch to more muted tones as the skunk streak that began in my 20's slowly took over my head. To my surprise, I still need high contrast. The black and white, red and navy that have been the core of my wardrobe, continue to be my best colours. In fact I have a much harder time now getting away with muted tones like grey or steel blue--they seem to make my head look grey, whereas my usual colours make it look dark with (lots of) frosting. I have now started wearing nude or taupe shoes with no lighter tone on top because it seems to bookend my hair just fine, so there's that.
I needed glasses from my mid-40's, and started out with thick black-framed nerd glasses, because that felt like me. Now, I can't get away from them (well, the ones I'm wearing today are burgundy), because they seem to provide the contrast that my hairline and eyebrows used to (I don't know what happened to my eyebrows, they didn't grey or fall out, but they are much less noticeable).
Eye makeup (even mascara) just doesn't happen. 1. I can't see to put it on without making a mess (and youngest daughter has left home) and 2. when I try, my eyes water forever. But I take heart from one of my style icons (haha can't recall her name but she's a New Yorker with silver hair and she's on my Pinterest board) who wears red lipstick and says her glasses are her eye makeup. Lipstick: I have always needed a quite dark lipstick as my "nude", or I looked like a palomino. Now my lips are so pale that there is a terrible contrast between the days I remember to put it on and those I don't. I have a harder time pulling off the really dark ones, and my search for a more midtoned nude for "summer" over the past few years has turned up a series of almosts. but I have found that by putting it on over Vaseline Lip Therapy (part of my morning routine, which has expanded horrifically in recent years) it looks more natural.
My biggest wardrobe obstacle has been hats. I love hats, wide-brimmed hats, they were always part of my signature (though sometimes needed a little squeezing to fit my actual lifestyle). But now, the glasses are one challenge, but the swath of white hair above my ears (men greying at the temples looks distinguished, but it seems to be the worst place on me) just sticks out like a sore thumb especially with a black fedora. I did find one hat that didn't have that effect--when I wasn't in the market for a hat--it was at Payless Shoes of all places, was woven straw with a very wide brim, and in alternating bands of taupe and steel grey. It looked great on, but just the fact that those dull colours equalled my hair was too depressing to consider it.
My new hat replacement for a signature, by the way, is scarves. This also takes care of the other problem that snuck up on me. I never used to understand what Nora Ephron meant when she said "I feel bad about my neck". Going grey isn't the last of the surprises in store.
