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 How to Wear Tall Boots and some cute outfits to go with them.

1. Knee 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 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 look long and thin.

Knee High Boots



2. Aim for No Gap

The perfect fit is key. Your boots should be tight enough around your calf, so there’s no gap (or just a tiny one).  They 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.

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

tall suede boots for women

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3. Suede Boots are The Comfiest 

Tall suede boots are your best choice if comfort is a priority because suede is such a soft, flexible material.   Also, since suede is stretchy, it’s great for skinny calves because 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 help. This classic black riding boot (above left) is stylish but practical too because it has stretchy knit panels built into the back of the boot to allow for expansion.

Boots for wide calves

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.

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6. Riding Boots are Your Friend over 40

A traditional equestrian style boot is practical and chic for any 40-plus lifestyle.  You can wear it with jeans or leggings tucked in, or pair it with a sweater dress or any other casual dress. 


7. 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 mindful of wearing boots with too many straps or too much bling to the office,  especially if you have a conservative workplace.  A simple, classic style like a tall brown or black leather boot looks more sophisticated and won’t date as fast.

8. Hosiery  Matters

Wear tall boots with a dress and semi 0r 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 see


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9. High Black Boots with Leggings are Sexy

For a casual look that is 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

If you want a modern casual look, try 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 I have worn to death!

Lug Sole



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.



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9 thoughts on “10 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.

    2. I’m 4’11 and the only ones that work for me are Clarks riding boots. Naturalizer has worked in the past too.
      It helps if they have elastic backs

  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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