Angie's advice is so wise (natch--haha!). Tall boots ARE hard to fit. Feet are hard enough, but add calves, and you've got a double challenge!

I let go of one pair of black tall boots that I loved a few years ago, and I actually don't miss them, because I kept a pair that is identical in olive (Donald Pliner, Devi 3). They are probably my most-worn tall boots now. I also have a tall black pair with an equestrian vibe (Blondo, Volly), a stretchy pair with narrow heel (Donald Pliner (Nikko) that I like to wear for as a pump substitute in winter, and a flat pair of brown ones that lace up the back (Sofft, Sharnell), which I was thinking of donating--until brown came back this year with a vengeance and I started having some current things I might wear with them again.

All of these boots are comfortable, and I would like to wear them more than I do. But I don't miss skinny jeans and pants, which was what I wore them with the most at one point. Skinnies were too tight on my calves. I have a couple of pair of slim straights that I can tuck into boots, but I rarely wear them that way. I'm more likely to wear tall boots with dresses, and I just don't wear dresses all that often. I'm intrigued by the suggestion of wearing them with shorts. I have some long shorts that I can envision trying with tights and tall boots.

I haven’t tried skinnies for a while but do like a slim straight style which is closely related.

I think the black simple boots are all classics and worth keeping. The lace ups I like but I don’t see them in keeping with your more recent looks.

I do wear my tall boots under wide leg jeans and pants too.

It’s funny, I never think to wear tall boots under my long pants, even since wider pant legs have been trending. But I can’t think of a time I want to do that — it’s not usually that cold here that I want that much warmth, but this week may challenge that!

I like the idea of wearing tall boots with long refined shorts, for those who wear shorts. For me, I’m just not a shorts person.

Sharan, in addition to the fit challenges of foot and calf circumference, the height can be a real challenge too! I know short-legged ladies feel like a lot of shafts are too tall, and on me a lot of supposed tall boots come about two-thirds or three-quarters up my shin. It’s not always bad, but sometimes it just doesn’t look intentional enough. Both my black lace up and tan suede pairs are intended to be over-the-knee, but on me, they just sort of reach my kneecap but don’t cover. That can be an awkward height too. So when I have a pair that truly works like the slate blue-grey Aquatalias, I will keep them for sure! Those are the one pair I’ve worn in the past two years.

Carol, if I let go of the tan suede ones, I’ll give you first dibs! Size 8 or 8.5 if that works for you.

Aren't you using the tall boots now with all this snow? I'm Very glad for mine!
I don't own skinny jeans anymore, but do have tuckable ponte and pleather leggings, kept for this reason!

I have 2 pairs of tall boots, one is heeled and the other is snowboots. I'm wearing the heeled ones especially under wide pants and jeans this year for warmth, but could wear with skirts too if I could be bothered with tights. I wore them with shorts too for Rocky Horror, but probably wouldn't otherwise.

No more skinny jeans for me but I could see coming back around to slim straights. I have one pair of tall boots that I keep even though they don't get a lot of wear. I only wear them with dresses, which I rarely wear, but when you need them you need them, so I will hang on to them.

Ok - this may not be funny to everyone, but it made me laugh : Meghan Markle was photographed the other day wearing tall boots under a pair of bootcut pants. You can clearly see the top of the boots through the pants. The comments on social media were gold. Ah, I love the internet sometimes.

Lisa, I can only imagine! And that is definitely a concern with tall boots under pants. I remember being annoyed years ago when the top of my cowboy boots would show under my bootcut jeans. I would take them off and choose something else instead.

Just chiming in to say after reading this thread I added my one pair of tall boots (black riding style; maybe 15 years old) into my donate bag since I no longer wear them. Yay me!

My tall boots only get worn with skirts and dresses and are dressy. I don't think I will ever part with the crazy patterned fabric boots as they are so much fun. My mid-calf boots are way more practical and work well with wide-leg jeans.

I'd confidently buy a cowlneck before I'd buy a pair of skinny jeans.

Hahahaha - Cee.  

LOL Cee, I’m with you on both counts!

So as we speak, my skinny jeans and two pairs of tall boots have joined the giveaway pile.

I’m feeling more clarity around how I want to dress now, and I’m also being more realistic about wearing opportunities. With our increased travel schedule, I’m not going to be able to wear a lot of my fab stuff all spring long. I’m being careful about buying for transitional seasons since that when I do a lot of travel.

Oh dear! Skinnies and tall boots are out? Does this mean I should return these? They were my first purchase when I started this wardrobe refresh (the blue ones were the only pair of jeans I had), but I have till Jan 31 to return them. They were only $35 each though. Is it a faux pas to wear skinnies now?

GoldenPig do a Google search for jeans & tall boots 2025 and it is clear the combo is not dated. Do the same for Leggings & tall boots 2025. Not low rise skinnies but slim straights are trendy. Leggings are good too. Just depends how you style the top half. Tall boots were not trendy for some time but had a resurgence last year. It comes down to personal taste too. As I mentioned in this thread faux leather leggings and tall boots are my favourite winter outfit right now. Keep the boots if you love them!

Natalie, wearing tall boots worn over skinnies is neither dated nor out! Taller boots have been trending for at least three years - albeit paired more with skirts, dresses, shorts, and relaxed bottoms.

My denim trends post for the year comes out every February. 2026 will be published next week. In the meantime here is last year's denim trends post:

https://youlookfab.com/2025/02.....-for-2025/

To Star's point, Slim Straights are fringe trending and gaining momentum, although they have HIGHER rises this time round. They are '80s skinnies to my eye - just not SUPER skinnies like we saw in the '00s. The low rise skinny is about the only denim and pants silhouette I am not seeing in this fashion era.

LJP, I just saw your question! Wearing volume over lean bottoms is not new - dead right! Let me elaborate: Back when skinnies were big years ago, voluminous tops were different than they are now. They were more in the draped and cascading tunic variety with asymmetrical hems. Fitted on the upper torso, shoulders and sleeves, and volume below it (very '00s). Volume in this fashion era - 20 years later - is big all over - throwback to the '80s and early '90s. Dropped shoulders, big sleeves, funnel necks, width on every dimension, extra length sleeves, and a whole lot of oversized toppers to choose from too. There are also very boxy shorter tops. Wearing the current assortment of voluminous tops over skinnies is a refresh. Hope that makes sense!

Right - I see, thank you ! I'm still not going there though ;).