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The Most Comfortable Women's Boots for Fall A Buyer's Guide 2023. I reach for my chunky black lace-ups time and again, whether I'm wearing jeans, midi skirts, or a cute dress.Day or night, rain or shine, I'll probably be wearing boots, which is why I've developed a pretty good eye for spotting the best boot trends over the years.What makes a good boot trend, in my opinion, is its. Partially recycled fabrics, more supportive insoles, more cushioned midsoles.