First look at the fall boots

Kristyn Schiavone
Tribune Content Agency

Nothing signals the end of summer like an influx of promotional emails about fall boots.

Every year, when my favorite retailers send me the “First Look: Fall Boots” email, I react in four stages:

Excitement: For most people, this stage is Denial, Part 1, but I happen to love fall and am usually not at all sad that summer is ending.

Denial, or Denial, Part 2: “Wait, do I need new boots? I feel like I bought a lot of boots last year, which should still be perfectly fine. Boot styles don’t change THAT much, do they?”

Panic: “Oh, no, they DID change! And I need them all, but boots are not on my fall list of things to buy, and I haven’t budgeted for them!”

Acceptance: This is the part where I decide to choose one pair and wait for post-holiday sales to buy the rest.

Typically, my pick for fall is a pair of ankle boots. While the weather is getting gradually cooler, you’re also going to have your fair share of warmer fall days and ankle boots are much more suited to this in-between weather. They can even be worn with dresses and bare legs in some cases.

Ankle boots have been on the hot list for a while, so below are some of the updates you can look for this season.

Mid-height heel

Gone are the days of spiked stilettos or flat-as-a-pancake soles. The look of the moment for ankle boots is a stacked heel of modest height, kind of similar to what you would find on a cowboy boot. This is great for ladies with foot problems, like me -- there’s enough height to give your arches some support, but not so much that you’re carrying your entire body weight on the balls of your feet.

This heel height also flatters your legs in much the same way as a stiletto, without the inevitable tripping, getting your foot caught in sidewalk grates or having to take your shoes off to walk home at the end of the night. Sign me up!

Thinner, pointer toe

Sounds a little bit like the Wicked Witch of the West, I know, but just hear me out. Ankle boots, especially those with a heel on the shorter side, have had a rounded toe for most of their reign as the most popular fall footwear. We’re not talking about the same look as a pointed-toe pump here, but as an update, consider a skinnier rounded or square toe. This is especially flattering if you have legs on the skinnier side. It offers a very streamlined look for your skirts with tights and legging-style work pants.


I’ve been staunchly opposed to this ever since I first saw it, and I’m changing my tune. My complaint was that it’s silly to buy a boot -- a shoe meant for winter -- that you can only wear through October. This seemed to me like a dumb way to spend money, when I could be buying a boot that’s good for eight months of the year.

At this point, I’m comfortable enough with the volume of boots in my closet that I would spend money on a pair specifically for fall, instead of buying another traditional pair. They’re great to wear with fall dresses, and it’s also going to be a while before your last summer pedicure wears off, so you might as well make the most of it.

Higher rise

There are a lot of boots on the market now that hit you right at the bottom of your calf, instead of your ankle. These are still technically ankle boots, but there’s a little more boot to work with. This is a chic way to wear a stiletto heel this fall. The one trick is to make sure it’s flattering on your calf, and the boot isn’t too tight at the very top.