Are Tall Boots In Style? How To Wear Them To Look Current

You know how they say fashion is cyclical… Well whoever “they” are, they’re spot on! Fashion is like this perpetual game of what’s out or what’s in - and then when you’ve lived long enough, it becomes a game of “oh, I remember when those used to be in - I can’t believe it’s back!!”

So, on that note, and because I’m way old enough to have lived through this at least two times… let’s chat about tall boots.

The last go around with tall boots was at its height circa 2010, when we wore flat riding boots, generally with a rounded toe, skinny jeans or leggings tucked in and some sort of longer sweater or top. And if you were really stylish, you’d add an infinity scarf for good measure.

I’d say that version of the tall boot outfit died somewhere in the 2014 range. For some it lasted longer, but it’s definitely been a dated look for sometime now. And for me personally, it’s been all about the ankle boots for the past decade.

But what goes around comes around, and in the last 18 months taller boots have been catching my eye and piquing my interest. I invested in these boots originally because they looked great with my midi skirts (and they were comfortable to wear for long periods of time, which is a huge bonus). And then I started seeing some of the younger, Instagram, ‘it” girls wearing tall boots over jeans and it looked really good. So I paid attention and watched and waited. And it gained traction…

As with any act two or act three, especially where it comes to fashion, there is always a slight twist that makes it feel new and different. In this case the shape of the boot and the proportion of the outfits.

How to Wear Tall Boots and Look Current

The bottom line is that flat riding boots over skinny jeans will likely still look dated. In my dream scenario I’d love to wear a flat boot because, ummm, heels often suck to wear. But I honestly have not found a pair I like that’s totally flat. Block heel or small heel, yes, but flat… sadly no.

Here are 5 quickie rules for styling tall boots:

Opt for a heel and pointy toe.

That slight difference, that makes all the difference. Having a pointy toe and a bit of a heel makes the silhouette look modern, and just a little bit sexy.

Pick texture or color.

Instead of the solid brown or black flat boot of yester-year, choosing a tall boot that has texture like snakeskin or suede makes it feel current. And then earn extra points if it has both texture and color, then it becomes your hero piece! The new taupe, suede boots I’ve been wearing on repeat, are case and point. And if you follow me on Instagram, you know this to be true.

Go slouchy, but show some waist.

Having a top that is somewhat oversized works well with tall boots, but to have it feel relevant, tucking in to show some waist makes all the difference. Even a half tuck or the one side of a button up tuck works. 

Don’t save tall boots for skinnies.

While yes, skinny jeans work well to tuck in to a boot, a slightly less tight jean looks fantastic too. That’s a newer way to wear it, so you might not be ready yet, but be aware, it’s on the horizon.

Style with skirts, both long and short.

As I mentioned above, tall boots pair perfectly with a midi. And they also look amazeballs with short skirts. In the colder months adding a sheer tight will keep you warm and looking fresh. I just ordered these sheer tights and they live up to the hype.

So, let me know if you’re feeling the tall boot vibe and ready to jump in, or if you’re in the wait and see camp. 

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