I feel your pain! It overlaps with my current goal of putting together some more elegant/ stylish looks that still fit me aesthetic and various limitations ( feet!).
You may have more options if you can wear dressy boots of different styles, because can add tights to skirt & warm top or a more substantial dress ( including underlayer option), then a dressy coat.
Or, you might think about whether you do better overall with a pants outfit , but need different items to look more special occasion/ dressy/ festive — cut, fit, fabric, coordination with a top +/- topper, and dressier accessories. I will include “ feminine “, or pretty, because I face that issue, that my pants and blazer outfits skew more preppy, tailored, workwear, so when I see so many other ladies in dresses for an event, I may feel off. It’s actually easier in winter because fabrics can be more luxe, such as rich velvets , cashmere, so tops can stand alone with tuxedo pants, or jackets themselves may be luxe and dressy, with pearls or sparkly or metallic jewelry and clutch. and underlayers are easy. I have huge footwear limitations so that my only dressy footwear is ankle- strap flats. Sleek pointy- ish boots no longer work.
So I’m finding it takes more intentionality for me, than years past when I could put something together from a variety of pieces.