5 classic styles of wide-fit high boots you’ll love over 50

Today, women of all ages wear knee-high boots for casual through to classy events.  If you’re over 50 and you’ve often thought this wardrobe staple would suit you, but were worried about high boots being too tight, then read this post.

I’ve picked out a range of wide calf boots to get you started on your research.

Styling the classic knee-high boot

Perhaps you usually select ankle boots, booties or uggs style footwear.  These are favorites especially because they are easy to slip into. But the traditional knee high boot gives you more of a classic elegance. And if you buy your boots in a wider fit, they should be just as easy to pop on and off.

If you have trouble bending then invest in a long shoehorn, and stick it into the boots when you put them aside so you remember to use it every time!

A classic boot works for older women under a midi skirt, a dress of any length, over narrow jeans and leggings, under wider pants, and makes wool coats and trench coats look chic.

Don’t worry that a classic low heel tall leather boot will look too masculine or heavy for a dress.  It won’t.

It will give definition to your leg and ankle and make your frock look even more feminine by contrast.

Beware, however, of the ruched high boot.  This does not give definition and, if you are plump, will continue those lumps and bumps all the way down to the ground.  Which is not a classic look!

If you like to dress in a casual or smart classic style then you should choose a pair of riding boots or very similar.

These come in all prices and right now (January 2023) you will find huge discounts on this must-have item for a classic wardrobe.

Note: my suggestions are linked to retailers I trust and  have an affiliation with.  So if you click and buy I may get a commission at no cost to you.  Thanks for your support.

Which retailers to look at for wide-fit high boots?

After looking at prices in the current sales, I noticed that Macy’s comes out the lowest.  I also like Macy’s ‘created for Macy’s’ styles.  They sell so many boots in so many styles that they have all the data needed to create winning designs.  So I’ve included many of their creations in this ‘best of high boots 2023’ list.  

I’ve also got one design from Clarks who have been making very well designed footwear with good arch support for decades.  They offer many wide fit boots so look around the site. Remember that boots for wide feet will mean an increase in the circumference of the calf of the boot too.

So let’s dive in and take a look at what makes the perfect pair of boots.  And I’ll give you suggestions for classic knee boots I think are very stylish and great value for money.

The classic leather riding boot with traditional straps, buckles and block heel.

This is a great way to add style to any cool weather daytime outfit.

The Jessie boot by Naturalizer is ideal for wearing with jeans or a thicker midi skirt.  

Zoom into the images on the Macy’s site to understand exactly how this high-shaft boot will flex and fit. Note the inside leg long zipper, the two areas of elastic at the calf and the calf buckles.  

Look carefully at the leather too.  It is polished but not a smooth leather.  So will look good against other natural fibres such as wool, cashmere, tartans, tweeds and denim.

The site gives full information on the calf widths and shaft height so measure your leg and check these before ordering.  Ideally you are looking to wear your jeans inside the boot.

It has a low non-slip block heel so you’ll find it easy to walk all day in these boots, whether outside or indoors.  It’s useful to have a boot that you can wear a thicker sock with in colder weather too.

The smart wear-anywhere high shaft suede boot

Looking for a more urban take on the classic boot? Then suede is a good choice.

And if most of your bags are tan, as mine are, here’s the Maye Shine boot by Clarks.  

You’ll see not only a zip but also a notch to widen the very top of the boot.  These will help with easily stepping into the boot and fastening it.   As all Clarks shoes, this model has a well-designed foot area so your toes are not cramped.  Clark’s own special footbed gives further support and comforts your foot from beneath to ensure you don’t develop blisters.

I like the dark tan color which will match up to many of my belts and bags and works for all seasons.   Tan goes very well with denim.  Style these boots with jeans and a longish cashmere sweater and a tan cross body bag or belt bag.  You’ll look cool, classy and casual.

The more fitted riding boot with added flexibility

If you want a shinier leather and no straps at the top, then take a close look at the Leigh wide calf riding boot.  It’s more fitted to your leg shape with a more close-fitting ankle.  The elastic down the back ensures it has the stretch your wide calf needs, even when bending your leg. 

This boot would look good under any weight of clothing including jersey dresses or a sharp white shirt under a blazer.  And the smooth top means it won’t catch on a frock or skirt.

It may be less traditional but it’s comfortable and feminine too.  

Just be aware that if you have larger calves your legs might look simply too curvy in a fitted boot.

Synthetic materials black classic riding boot with faux leather trim.  Deliee by Karen Scott.

The modern take on the riding boot

Here’s a good-looking boot that hits that midpoint between authentic riding boot and stylish accessory.

Karen Scott’s Deliee high boots for larger calf widths is inexpensive.  This is a boot that will last you for a year or perhaps two but it will look lovely during that time.  All synthetic materials.  

Check the calf measurement against yours.  It tends to be less wide than some other boots I’ve picked out.  

I like the gold buckles and the long straight leather-look trim which adds a classic note of structure to this modern boot.

Style this boot with leggings and a knitted sweater dress to the knee.  Add a bright silk scarf and you have an on-trend outfit. (If your legs are slimmer, or if you’re younger, you should wear your sweater dress so it hits above the knee – just depends on how bumpy your knees are these days.)

The stretch-to-fit tall boot

I love the colors available in the Genia boot by Impo which includes a strong red!  This boot is made with synthetic stretch materials so it will be calf-hugging.  The outside is faux suede which will look excellent under a contrasting dress or skirt.

A navy mid-weight dress would look excellent with the red boots. You’ll look younger and more self-assured. So this combo would work for giving a presentation at work through to dinner at a restaurant with a special partner.

If you wear straight or wider pants then this is the type of high boot that will go beneath them. If you wear pants in the same color as the boots, for example black or navy, you will lengthen your leg so it doesn’t look as wide.

The foot of this boot is solidly structured and has a slightly rounded toe to look stylish and feminine whilst maintaining room for your toes.  The rubber sole and memory foam inside ensure this boot will be as comfortable as sneakers.  

And the wedge heel is a godsend as it gives you height but doesn’t make you look top heavy, in the way thin high heels do if you’re carrying extra weight.

More style tips

If you want to read more style tips about wearing boots, take a look at my previous post on wider boots. The boots suggested in that article, all from UK online retailers, will be out of stock by now but you might find my comments of use.

Looking for inspiration to get that closet sorted? Too many clothes but nothing to wear? Take a look at my Mature Style Course. It works with you, step by step, to create a wardrobe of clothes that are right for your shape, your lifestyle and your budget. In fact you may not need to buy a single new item!

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