Style guidelines often suggest leaving a gap of leg, skin or hosiery, between the top of tall boots and the hemline of your dress or skirt because the visual effect is more flattering. Of course, with on-trend longer hemlines, “the gap” is not achievable with tall boots. So what are we to do? 

Well, I’m lukewarm on this guideline in the first place. To my eye, tall boots look great with shorter hemlines that create the gap, and they also look great with longer hemlines that close the gap. My 2008 post on the skirts skin boots sweet spot shows a variety of skirt lengths with boots, and the last photo is a midi sans the gap. It’s a ’70s look that I have always liked.

The photos below show “gap-less” hemline and tall boots dressing. The key to making this combination feel sleek is to wear relatively plain tall boots that are slim-fitting at the ankle. Yes, it’s also very ’70s to wear boots that are wide at the ankle with midis. That combination has it’s fashionable place, but is harder to pull off. It’s usually best when the heels are very high. 

I like to wear my low heeled, slim fitting knee-high black patent boots with midi skirts and dresses, both pencil and flared. No gaps! What are your feelings on the gaps or lack thereof when wearing tall boots with skirts and dresses? 

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