9 Tips For Looking Fabulous After 40 in Tall Boots

There’s nothing like a pair of tall boots to make you look modern, sexy, and chic. Whether they are knee-high stiletto boots or low-heel riding boots, a pair of gorgeous boots will rock your wardrobe.

Here are 9 Tips for How to Wear Tall Boots:

How to wear tall boots l tan tall boots with navy sweaterdress and tan bag l styled by Fabulous after 40

1. Knee High is Most Flattering

This season you’ll find tall boots in a variety of heights, from mid-calf to over-the-knee, but the most flattering boot is one that ends below the bottom of the kneecap.

Mid-calf boots stop at the widest part of your calf, cutting you off vertically. They’re not the best if you have chunky calves because they can make your calves look even wider. Over-the-knee boots or thigh-high are fun but can be tricky, especially if you have short legs. They can swallow you up or put too much emphasis on your thighs.

Knee-high boots like these Dress Boots create a long, lean line that makes your legs look slim.

How to wear Tall boots l tall lslouchy taupe sued boots with rust and taupe floral dress l styled by Fabulous After 40


2. Aim for No Gap

The perfect fit is important. Choose a  boot that is tight enough around the calf, so there’s no, or tiny gap. Your boot should be sleek and fitted but not tight. There shouldn’t be any skin bulging over, but they’re also shouldn’t be more than a half-inch of space between your boot or your leg either.  Otherwise, it takes away from that tapered, streamlined look.

Note: Flat riding boots like these below have a straighter fit and are more rustic, which means you can go with a slightly wider boot.

How to Wear Tall Boots  l over the knee black suede boots with leggings and a poncho styled by Fabulous After 40

3. Suede is Most Comfy

Tall suede boots for women are your best choice if comfort is your priority because suede is such a soft, flexible material.   Also, since suede is stretchy, it’s great for skinny calves. It molds to thin legs like a glove. If you have large or muscular calves, leather boots are better.

Boots for wide calves

4. Large Calves Need Extra Features 

Speaking of large calves, you’ll need to look for boots that measure 16″ or more around. Boot with full side zippers and elastic panels also help. This Chelsea Sweater Knit Shaft Riding Boot ( above left) has stretchy sweater panels at the back. It is chic but practical because of the added stretch all along the back of the calf.

5. Skinny Calves Need Insets

At the opposite end of the spectrum are women with skinny calves. Ladies, you need boots that measure 13  3/4″ or less around. Also, look for boots with elastic inserts sewn into the shaft for a tighter fit. These Stitches Over the Knee Stretch Boots are a good example of that.

Tall merlot suede boots with merlot turtleneck, faux fur vest, black jeans and balck bag styled by Fabulous after 40.


6. Colorful Suede Boots are Trendy

If you want a fashion-forward look in a tall boot, then consider a colored boot. It’s fun for weekends when you want a little wow.


Colored tall, flat suede boots are also great for a casual look and work with jeans or leggings. I bought these Tall Suede Merlot Stuart Weitzman Boots this fall, and I love them!

7. Wedges Give You Height Without Hurt

If your feet ache, but you want height, consider a wedge heel that distributes your weight more evenly, making it easier and more comfortable to walk in tall boots.

8. Hose Matters

Don’t forget to pair your boots with opaque tights for a modern look.  Your tights should match the color of your boots to elongate your legs and make them look lean and sexy!

9. Classic Styles are Best at Work

Tall boots can add an edge to an office outfit. A stacked heel with a rounded toe is the most comfortable type of boot to wear to work.

A stiletto heel with a pointed toe is also acceptable and is more elegant and alluring.

Be careful of boots with too many straps or too much bling on them in the workplace. A simple, classic style like this tall brown boot looks more sophisticated and won’t date as fast.

black riding boots with buckle worn with black fringe cardigan and jeans outfit.


10. Riding Boots are Your Friend over 40

An equestrian style boot like this Derby Riding Boot (above) is practical and chic for your over 40 lifestyles.  You can wear it with jeans or leggings tucked in, or with casual dresses. 

Join the Conversation

7 thoughts on “9 Tips For Looking Fabulous After 40 in Tall Boots

    1. Have you looked in the kids section? Many people recommend buying Hunter boots in kids sizes. Maybe it would work for you.

  1. I bought caramel colored suede over the knee for this season. So chic with leggings, long tunic sweaters, & jeans, Pop on a slouchy scarf paired with a felt fedora, & sunglasses and rock the look. Every time I wear those boots, someone compliments me.

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