See 9 Great Ways How to Wear Tall Boots (Guide)

Whether your winter weather requires wearing knee-high footwear or not, this post is your guide for looking effortlessly stylish in tall boots. Read how to wear tall boots now.

Disclosure: There are affiliate links in this post.

Invest in Great Classic Boots

Boots are a great investment in your wardrobe from both a style and price point of view. You don’t buy them every year, but rather when you need a new pair either because the old ones need to be retired or a life event has changed the size of your feet. Since their tenure in your closet will be several years, your best bet is to go for an ageless design, i.e. a classic style that can’t be pin-pointed to the year you bought your boots. Thus, this is a case where you don’t search for a bargain, but splurge.

Expert tip: Go for the best quality that you can afford without breaking the bank.

Tips to Find the Right Boots

Here my tips what to look for when you shop for a new pair.

1. Skip styles that end at the widest part of your calves. Remember that any horizontal line draws attention to the point where it occurs. The point of your calves is surely not where you want the attention. It would make you to look heavier than you are. Nobody needs that!
2. Stay away from cuts that are too wide at the top for you unless they are slouchy. You should be able to put two fingers into the top when you intend to wear them also over jeans. Otherwise one finger is enough for comfortable fit and style. Great fit at the leg is important to avoid a cold gap. You also do not want to look like you are “standing in your boots.” You are not Grandma Duck. That look is reserved for styling rainboots and wellies.
3. When the boots are the only pair you will own, go for a sturdy heel (that you feel comfortable walking in), leather in a neutral color of your color palette and classic style. This design will work for the commute to the office, visiting clients/customers, having a work lunch with your boss and walking on snowy sidewalks.
   1. Let the colors of your wardrobe be the lead in the choice of the neutral.
   2. Go with black or gray when cold colors dominate.
   3. Tan or brown are good options when most of your clothes are in warm colors.
   4. Only go for a statement color or style, when the pair is your second pair, i.e. never buy a statement piece, when you need a work horse. More on styling statement shoes.
4. The fit on your feet is critical. Your toes should not be squeezed in the toe box to avoid cold feet. Because air is a good insulator, you want a thin air layer between any winter footwear and your feet.
   1. When you live in a cold climate region, the toe box should have enough room for wool socks and a shearling or foam insole for insulation. Consider going a size up.
   2. Waiting for the bus or tram can be uncomfortable when due to lack of insulation to the ground your feet get cold. A thick sole is also a factor to consider.
   3. On very cold days, you may consider to add socks or boot toppers as they “elongate” the boots and close the gap between the leg and the boot. See this post for how to style boot toppers over 40.
5. In cold climate regions, consider wearing over-the-knee boots to keep your knees warm. When buying OTK boots look for a classic style with sturdy heel and stir away from patent leather (wrinkle alert) and stiletto heels (pretty woman alert, dangerous on ice). Leave stiletto patent leather OTKBs for dancers like Jasmine Dubrow in Independence Day and women in the horizontal profession like Vivian Ward in Pretty Women.

Expert tip: When buying boots look for a classic style with sturdy heel.

How to Wear Tall Boots the Modern Way

Here are a couple of styling ideas, Dos and Don’ts for work appropriate looks with boots.

1. When your legs are your favorite/best feature, try a knee-high pair with an above the knee-skirt. Don’t go shorter than 4 inch (10 cm) above the knee. You don’t want to be mismatched from behind with your daughter or look like you are reliving the 1960s. 😉
2. Unless the 70s are a trend, avoid to wear a midi skirt that covers the upper part of your boots. Because this look is so 1970s, it ages every woman who was already alive in the 1970s. Therefore, if you go for the 1970s style, keep everything else modern.
3. It is so much sexier to show some skin between the boot and the hem of the skirt. However, be aware that this glimpse of skin – even when covered with pantyhose – is a cold gap. Therefore, wear a long coat.
4. When wearing a leather skirt go for suede boots and vice versa.
5. Going for a riding-style or over-the-knee boots are other great option. Pair them with slim pants (skinnies, riding pants, jeggings or leggings), a button-down shirt, blazer and scarf. Add a pearl necklace and diamond studs for a posh casual business winter outfit.
6. Over-the-knee boots look great with skinnies under a long tunic length sweater or a tunic dress.

Outfit Ideas for Tall Boots

Here are some outfits with boots for visual inspiration.

Equestrian Styles Are Timeless

Riding boots look great with skinny jeans, leggings, denim or tweed skirts.

Studs Another Way than under the Sole

I love studs. Therefore, when I found these Valentino studded boots for a bargain on eBay my “buy now” finger couldn’t resist. Unfortunately, they have an expensive leather sole that is perfect for southern European urban environments. However, they are like sliding shoes on snow and ice. I tried to fix the problem with an anti-slip sole, but the cold ground disaggregated the clue. After a short walk, the gained grip was gone as the anti-slip sole fell off. 🙁 Thus, I now wear my Valentinos prior to the snow season and after snow melt.

How to Wear Tall Boots in a Statement Color

This summer, I searched eBay for tall footwear in a statement color. Actually, I had burgundy or red in mind. However, then I saw these Jimmy Choo turquoise shearling beauties for less than $50 with shipping! I had immediately, more than three outfits in mind – one of my criteria to buy a new addition to my wardrobe. I am happy that I gave up on red or burgundy for turquoise. Believe it or not, they are so comfy despite of the high heels. Those ladies who can afford to buy Jimmy Choo at the original price tag, are so fortunate! Here two inspirations what to wear with knee highs going out for dinner.

More examples with these shearling beauties in this post on looking stunning in turquoise in winter.

Get More Options With Shoe Accessories

In Alaska, tall boots have a long season. Once the first snow is on the ground and stays, skirts or dresses need knee-high footwear on clear days. In winter, days with clear sky are usually much colder than those with cloudy sky. On the warmer, cloudy days you may get away with tights and booties. However, under clear sky winter conditions, tall boots are a must with a skirt or dress.

You can easily change the vibe of a pair by wearing mature looking boot-toppers. It’s also a great way to increase the insulation on a cold day.

Stylist’s tip: You can easily make your own pair by sewing faux fur at the top of knee-high socks. To save even more, consider buying a pair of men’s socks.

Given that in the Interior, the cold season can last from mid September to early May, I have invested in a timeless collection of tall footwear as I am a skirt/dress kind of gal. The goal is to look ageless in boots.

In winter, Alaskan women come to work in mukluks, galoshes, booties, and alike. In their cubicles, they switch into pumps. They schlep their pumps back and forth in a tall bag. However, at the end of winter, most of them have quite a line-up of pumps under their desks. I am one of them 😉 .

Final Remarks on How to Wear Tall Boots Now

When you live in a region with cold and/or snowy winters, tall boots are a Must-have. Invest in a timeless pair in a neutral of your wardrobe. Add a second timeless pair in a different neutral when you can afford it. When the tall boots are just for style, either go for a cheap trendy pair (and wear it again and again that season), or invest in a classic neutral pair for seasons to come.

How do you style your boots? What kind of boots do you need? Let me know, I am curious.

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Photos of me: G. Kramm

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