I think it would probably look a bit dated if you wore it with a neat shirt & plain court shoes as per 1990s office style. I certainly don't think it's ghastly (though I'd probably go for a longer style as this would be knee-length on me).
However, pencil skirts are very much back on the catwalks (if not so much in high-street shops as yet). As is grey ...
My answer to updating anything on S&B right now seems to "Dries Van Noten" - which is pleasing me greatly as it's not been the "right" answer for quite a while (not that I believe in right answers as such, but if you're uncertain & want to know how to update something ... then some answers will be deemed more relevant & current than others!).
Have a look at some street/catwalk ideas, but generally I would suggest wearing something more oversized on top (a shirt with exaggerated cuffs, a big slouchy fluffy jumper etc). Layering (especially if, say, it's a transparent shirt under a knitted opaque cardigan), is also very DVN. And mix in other patterns, like a check jacket. You can then wear plainer shoes like courts & pair them with socks - maybe embellished. Long boots if you want something more elegant - but play around with colours, not just grey/black/white. Or wear chunky boots for a more casual look. Jewellery - long beaded or crystal tassel earrings &/or necklaces.