10 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’re knee-high stiletto boots or low-heel riding boots, a pair of gorgeous boots will rock your wardrobe.

Here are 10 Tips for wearing tall boots and some cute outfits to pair with them.

1. High Boots are the Most Flattering

Tall boots come in various heights, from mid-calf to over-the-knee, but the most flattering boot is one that ends below the bottom of the kneecap. The reason?

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 boots are fun but can be tricky, especially if you have short legs. They tend to swallow you up or put too much emphasis on your thighs.  Knee-high boots are perfect since they create a long, lean line that makes your legs appear longer and thinner.

2. Aim for No Gap

The perfect fit is key. Your boots should fit snugly around your calf, with no noticeable gap (or just a slight one).  They should be sleek and fitted but not tight. There shouldn’t be any skin bulging over, but there also shouldn’t be more than a half-inch of space between your boot and your leg.  Otherwise, it detracts from the tapered, streamlined look.

The exception is riding boots, which have a straighter fit and are more rustic in appearance. These can be slightly wider around the leg.

3. Suede Boots are The Comfiest 

Tall suede boots are your best choice if comfort is a priority, as suede is a soft and flexible material.   Additionally, since suede is stretchy, it’s ideal for those with skinny calves, as it molds to thin legs like a glove. If you have large or muscular calves, leather boots are more flattering.

4. Large Calves Need Extra Features 

If you have large calves, you’ll need to look for boots that measure 16″ or more around. Boots with full side zippers and elastic panels also provide added support. This classic black riding boot (above left) is both stylish and practical, featuring stretchy knit panels built into the back of the boot to allow for expansion.

5. Skinny Calves Need Insets

Do you have skinny calves? Then you will need boots that measure 13  3/4″ or less around. Look for slim calf boots or boots that tie or lace up the back.

Tall boots can add a touch of 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 mindful of wearing boots with too many straps or too much bling to the office, especially if you work in a conservative workplace.  A simple, classic style, such as a tall brown or black leather boot, looks more sophisticated and won’t date as quickly.

8. Hosiery  Matters

Wear tall boots with a dress and semi- or opaque tights for a modern look.  Your tights should match the color of your shoes to elongate your legs and make them look lean, and see

9. High Black Boots with Leggings are Sexy

For a casual look that’s sexy, try a pair of tall black boots (to the knee or over-the-knee) with leggings and a tunic sweater. Just make sure that sweater is long enough to cover your bottom and private parts!

10. Lug Sole Boots are Trending

For a modern, casual look, consider a pair of tall, flat suede boots in burgundy, dark blue, or dark green. They are fun for weekends when you want a little wow. I own a burgundy pair that I have worn to death!

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.

Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

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