I sort of want more flat ankle boots for winter. Black, as usual. I'm thinking through what (if any...) holes I have in my shoe collection and whether I want to follow any trends or do my own untrendy thing.

I own two refined ankle boots and two RATE boots (photos below):

• Allsaints pointed-toe boots, mid ankle, workhorses
• slightly glitter-y booties, low ankle, rarely worn
• a variant on classic Dr Martens, mid ankle (they look more like boots and less like sneakers in person)
• laced combat boots from Madewell, high ankle; former workhorses that I've shifted away from

Possible additions that have caught my eye (Finds below) -- I could buy one or maybe two of these.

• Frye engineer 8r boots (an insightful birthday present from my boyfriend, to be ordered - I haven't tried them on yet)
• Theyskens Theory boots (wanted since they were new, and currently cheap on ebay - the Find is a different color but I'd buy them in black)
• Atelje sneaker boots (bought, but can't decide if the size is right)

One trend this year seems to be taller, fitted ankle boots like Angie has been wearing with cropped jeans, either zipped or chelsea. Another (not new this year) is low booties with skinny jeans rolled above them. Of course, I don't always follow trends, but I worry that the clunky Frye boots or the Theyskens boots with intentional giant flowerpot effect are past their peak trendiness, though I could certainly 'own' the look.

In terms of how they'd fit into my wardrobe, I can picture the Frye boots with relaxed skinnies (my current favorite silhouette). The Theyskens boots would go with true skinnies or tights and skirts; these seem less versatile and less useful. The Atelje sneaker boots are a bit harder -- boyfriend jeans or relaxed skinnies rolled at the ankle, or maybe my R13 jeans or cropped cigarette jeans like Angie's (I found a pair at Zara that I might buy, despite having too many jeans already). I worry that they'd be too sporty for me, but there's something about them that I love, a bit of a Rick Owens vibe.

Should I look for something sleek and mid-calf instead of these? Other trend ideas? I could do a slight heel, by the way, but not much higher than the Frye boots.