The Boot Edit: How to Update Your Boots for Fall 2025
Boot season has finally arrived. For some, that means yelps of joy. For others, maybe a tear or two as we say goodbye to sandals for a while.
You know me, I’m all about having wardrobe pieces that last for years and making smart updates that keep your outfits looking current. Boots are one of those key updates that can instantly modernize your wardrobe.
Why It’s Time to Reassess Your Boots
Lately, with many of my personal styling clients (especially newer ones), we’ve been doing major boot updates. Why? Because jean silhouettes have changed.
Wider-leg jeans are everywhere right now, and those older boot styles that worked perfectly with skinny jeans don’t always pair well with today’s proportions.
A few weeks ago, I wrote about The 5 Shoes You Need for Fall, and two of those were boots. So let’s go a little deeper into which boots to look for, which to skip, and why the right pair can make your whole outfit feel fresh again.
1. The Everyday Ankle Bootie
If you’re only buying one new pair of boots this year, make it a versatile ankle bootie. Depending on your lifestyle, you’ll probably want two versions:
A comfortable, walk-all-day bootie for daytime
A sleeker, dressier bootie for evenings out
What Makes an Ankle Boot Modern
There are two key features to look for:
A more elongated or pointed toe box.
Ten years ago, we were cuffing our skinny jeans above chunky, round-toe ankle boots. But now, wider pants call for a sleeker, more refined toe shape to balance the proportions.A taller, narrower shaft.
The shaft should fit close to the ankle and shin, ideally about four fingers above your ankle bone (roughly 6–8 inches tall). That slimmer fit keeps the bottom of your outfit from feeling bulky and helps transition cropped pants or jeans into colder months.
Ankle Bootie Style Tips:
Look for a pointed or almond-shaped toe
Choose a slim shaft that hugs the ankle
Opt for a shaft height of 6–8 inches
Shop Ankle Bootie’s with Tight Shaft:
2. The Tall Boot
Tall boots are having a major moment again and they’re so versatile. Whether you’re pairing them with dresses or tucking them under trousers, the right tall boot instantly elevates your look.
If You Love Midi or Maxi Dresses
Go for a tall boot with a narrow shaft that fits close to your leg. This keeps the silhouette streamlined under skirts and dresses and avoids bunching.
If You Prefer Shorter Skirts or Skinny Jeans
Try a looser-shaft style that lets you comfortably tuck in a slim pant or modern skinny jean.
Fit Tips for Tall Boots
Tall boots can be tricky for fit, especially if you have muscular calves or longer/shorter legs. Luckily, there are more wide-calf and varied shaft-height options now than ever before.
Before buying, measure:
Calf circumference (at the widest point)
Shaft height (from knee crease to heel)
Knowing these numbers will help you find boots that actually fit your proportions, not just the sample model’s.
Shop Tall Boots with Tight Shaft:
Shop Tall Boots with Loose Shaft:
Shop Wide Calf Boots:
The Bottom Line
Boots are an investment, and the right pair can last for years. But updating your shapes and fits to work with today’s silhouettes will make your entire wardrobe feel new again.
Start with a sleek ankle bootie and a tall pair that flatters your proportions, and you’ll be ready for anything this fall (including sandal season withdrawals).