Today I switched out my sandals with my tall boots in my closet (everything else stays visible year round). I’ve been thinking about reviving my few pairs of old tall boots, as well as my cowboy boots.

The last time tall boots were trending, it seemed to be all about tucking skinnies into those boots and wearing long tops and sweaters over it all. I do still have some straight leg jeans that will tuck into tall boots, but I’m also interested in perhaps giving some of my skirts some play this fall and winter. I love the look of a great long sleeved midi dress with tall boots, but I have no casual winter dresses at all anymore. I haven’t seen any that appeal to me in the last couple of years, and this year doesn’t look terribly encouraging either, so for now I’m thinking of midi skirt with tall boot ensembles.

In the process, I’ve pulled two pairs of tall boots out of my holding zone:

Pics 1-4 A very old (pre YLF) pair of slouchy harness Fryes in a taupe color that is not the easiest to work with in my black-dominant wardrobe. I used to wear them over skinnies with a black and taupe top a million years ago, but I’m not sure I’m feeling them with skirts. I have no other taupe in my wardrobe except for in prints. Slight tangent — I’m trying the boots on here with another very, very old piece that has spent years in my holding zone. I adore this suede patchwork skirt, but I’m afraid it’s a little short for my current preferences. I was a size smaller when I wore it, so it sat lower on my hips and gave me a little more length. I’m not so sure the proportions just are right on me now, unless I lose ten pounds again. I should try this skirt on with black tall boots or black booties and black opaque tights, which is how I used to wear it. OK, back to the Frye boots — I lost energy to try these boots on with any other skirts for now, but I wanted to show them and see if you all had any thoughts. They are ok, comfort-wise, not amazing, and they’ve always sat a little crooked on me — one slouches more than the other. I haven’t worn them in years and wonder if I should sell them or keep and try to work with them.

Pics 5-13 Then there is this pair of tan suede OTK Seychelles boots — I love the fit and they are super comfortable, but the color is a bit out of my norm. They just barely hit the top of my knee so I would always cover the tops of them. I’m trying them here with my patterned skirts that seem the most likely to “go” with them. Do these seem to work at all for me? I wish they were black, then I’d probably wear them a lot more. But is that just my comfort zone talking?

Pics 14-15 My other tall boots — burgundy RATE suede Borns, black leather and neoprene Weitzmans, and color-blocked black and grey Sorels, plus a pair of black lace up Kelsi Dagger that would be OTK on most people but come up to the bottom of my kneecaps, LOL.

Pics 16-18 My cowboy boots — some are very old and so broken in I would be reluctant to let them go. The ones in 16 are mid calf and the other are shorter, which makes them a little harder for me to style, but they have been worn under bootcuts in the past. The last pair has been living a hard life at the ranch, LOL. Any suggestions for fresh styling of these?

Are you all planning on reviving tall boots this year after years of wearing short booties? How are you styling them? Are you buying new styles?