Dressing up in the winter is tricky. Dressing stylishly in the winter is tricky. Dressing up, stylishly, in the winter in a way that will not piss off your conservative grandmother is just about as tricky as it gets.

I used this look from Town & Country’s style writer, Sarah Bray, as my style inspiration, whose collective chicness may, in fact,  tear a hole in the time-space continuum. Here’s her taking neutral pairing to a new level at a place called The Lobster Club (???) and here, gifting us some winter floral realness. God, I die. 

Plaid maxi skirts will be a go-to for me this season, because they are easy to style, easy to wear, and easily transferable from work, to dinner, to your couch afterward (they also second as a personal throw blanket.) I snagged the one my photographed in from Amazon for $36, and I’m wearing a size small. It has pockets (!!!!) and is paired with over-the-knee boots.  While it isn’t available on Prime any longer, it looks like it’s in stock and you should have within a week or so.

 The wrap and bow earrings are also from the ‘zon, and I’ve linked those below, as well. Oh, and if this photo look awkwardly forced, it’s because I made my Dad take it of me in our church’s parlor after my parent’s suggested we arrive a cool hour and ten minutes early for church #StopPunctualPeople2017. 

I also pulled some other maxi skirt’s I really, really love — specifically this grey large plaid print — each of which are less than $50. Pair it with a turtleneck (my favorite here), leather jacket, and velvet hair ribbon for a sophisticated look that won’t leave you looking like an off-duty nun.