A Tall Boot Look Book

I am mostly an ankle boots kinda girl. I just find them easier to style, I know exactly what to throw on with an ankle boot, and whenever I don’t know what shoes to wear, I will usually reach for my black heeled ones. Or sneakers.

But I do have some taller boots in my collection (I shared my most recent pair in this post) that I love as well. I just always need a little more styling inspiration. So, since November is my month of falling in love with all the fashion pieces I already own, I figured I should find some ways to style those taller boots. And thus this Tall Boot Look Book is born.

I have 3 pairs of knee high or over the knee boots in my collection, and for each boot I tried to find 2 looks that I can absolutely see myself wear, or in some cases have already worn. I sort of tried to do a more casual and a more dressy look, but not really as some of these boots are just very casual, whereas others just give every outfit a more fancy dressed up look. But at least I tried, okay?

Anyways, let’s just get into the looks.

Flat winter boots from Aqa

This is what I mean by “some boots are just casual” because my flat winter boots just make every outfit look more casual. They are the boots that I wear on those really cold winter days, when my toes will just freeze of my feet if I’m not careful. These leather boots are lined with a lovely woolly material (I’m guessing that “woolly material” is literally just wool) which makes them so nice and warm, but I feel like it does make them very very casual.

Sweater: H&M – Gilet: H&M – Jeans: Levi’s

So I figured for outfit number 1, why not stick to the casual winter vibe? And what is more ‘winter’ than knits and a snowy colour palette? I honestly never thought to style these boots this way before, probably because I didn’t have white jeans before, but I am so pleased with how this outfit turned out. The light colours keep the outfit fresh, but the cozy knit paired with the shearling look gilet makes it so winter appropriate and also nice and warm. I will definitely wear this look this winter!

Blazer: Mango – Dress: Only

I did actually try to dress these boots up a little bit for look no. 2, and I feel like I did alright. This was the outfit I was wearing when I tried these boots on and I really quite liked it, still do. The top half with the dress and blazer can be pretty dressed up, but I feel like the boots bring it to that ‘cozy day out’ level, and I am here for it. I would 100% wear this to the office on a cold day, when I still want to feel a little fancy. If you wear a long-sleeved t-shirt underneath the dress, and a pair of cycling shorts or something like that on top of the tights, it can actually be quite a warm outfit.

Knee high boots from Sacha

Because these boots are the newest addition to my tall boot collection, I still have a million styling ideas in my head, but I narrowed it down to two quite different looks: something a little more cool and casual, and something a little more dressed up.

Blazer: Secondhand – Top: Mango – Belt: Secondhand – Jeans: Levi’s

Look number 1 is obviously the more cool and casual one. I just had to throw in a mostly black outfit, because it is a colour I love to wear just because of how easy it is to style. To incorporate a little more of the brown of the boots into the rest of the outfit, I did add a brown belt, although it does annoy me that the colour match isn’t perfect. Still, I like how the overall look turned out. It is very much in my comfort zone, but to me it isn’t at all boring and actually I feel like it looks pretty chic. Again, I tried to keep it all nice and warm and cold weather appropriate because we need that here in the Netherlands.

Sweater: Axiome via Hudson’s Bay – Belt: Secondhand – Skirt: Secondhand

The second outfit with my Sacha boots is the exact outfit I was envisioning when I thought about getting these boots. I’ve been seeing those ‘midi skirts/dresses and tall boots’ looks all over Pinterest and Instagram and I wanted in on the trend. I love how this look turned out, and I have actually already worn it to the office. I love the very warm toned colours and how it is almost a monochrome look but obviously not quite. Even though I am wearing a skirt, I can still very much warm up this outfit with a pair of leggings underneath, because since the skirt covers the top of my boots anyway no one will know. The sweater I am wearing here is cashmere, so it’s incredibly soft and warm, but I did a similar look last year in my holiday look book with a thinner turtleneck top and loved that as well.

Over the knee boots from Mango

On to the last pair of boots in this look book: my over the knee Mango boots. I feel like OTK boots have become kind of a classic autumn/winter item over the years, whether they are heeled or flat, and I love love love the look of them. Although I like how these boots look, they just don’t stay up all that well on my legs, so I am still kind of on the hunt for a better fitting pair. Still, for styling purposes they work great. I feel like where the flat winter boots make any look a bit more casual, these OTK dress up whatever you wear just that extra bit.

Dress: Only

For my first look with these boots I went very simple: a sweater dress, another staple in any winter wardrobe in my opinion. I opted for bare legs, although maybe a pair of nude tights wouldn’t be a bad idea, but because most of me is covered that little bit of bare leg isn’t the worst. Just as long as you wear something underneath your dress to keep you nice and warm. I quite like black and brown together, especially of it is a lighter shade of brown like this dress, but I feel like a creamy white dress would look lovely as well. Just because of the bare legs I wouldn’t personally wear this look to the office, but it is perfect for date night, lunch with friends, a day of shopping (okay but then maybe with flat boots), a Christmas dinner… Basically all the things we won’t be doing for a while I guess. But hey, a girl can dream right?

Top: Mango – Skirt: H&M

My second OTK boots outfit, and the final look of this look book, is one that I would wear to the office just because it is a liiiitle more covered up than the last one. As in, I am weraing tights. I just love the vibe of this outfit, the all black with that lighter coloured skirt just to make it a little more interesting. OTK boots always work really well with skirts and dresses in my opinion, because they keep your lower half a little warmer, so you can get away with a little more upper leg showing. I would 100% wear this outfit with my tan beret for those ultimate French vibes, kinda like I did in this look.


I hope you got a bit of outfit inspiration from this post, I know I sure got a lot of outfit ideas when I was putting all of these looks together. I now cannot wait for a snow day so I can wear that first look in the snow and get a cute photo. Although, with the winters we’ve been having these past few years, I don’t know if snow is a realistic option… Guess I’ll just have to settle for this look in a frosty back yard 😉

Thanks for stopping by ❤

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