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Shearling coat with hat, Russian scarf, GNW tight, Vince Camouto boots, gloves and Celine bag (all own)

Whether your winter weather requires wearing knee-high footwear or not, this post is your guide for looking effordlessly stylish in tall boots.

  1. Invest in Great Classic Boots
  2. Tips to Find the Right Boots
  3. Styling Tall Boots
  4. Outfit Ideas for Tall Boots
  5. Equestrian Styles Are Timeless
  6. How to Wear a Statement Color
  7. Studs Another way than under the Sole
  8. Get More Options With Shoe Accessories
  9. Final Remarks
  10. Stylish Monday November

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

Invest in a pair of classic tall boots as your workhorse. #agelessstyle Click To Tweet


style influencer in gray boots and sweater with purple with fuchsia assymetric pencil skirt

stylist in purple, fuchsia, gray skirt, sweater, scarf, tights, boots classic winter look

over 50 years old fashion blogger in winter American Classic outfit

style book author in sexy pencil skirt
Outfit details: Rita Phil custom-made pencil skirt, Vince Camuto suede boots, Hermes collier de chien bangle, Hipstik tights, GNW cashmere merino wool sweater, Anne Klein scarf, The Pearl Source Akoya pearls


Please feel free to pin the photos to your Pinterest post.

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.
  4. The fit on your feet is critical. Your toes should not be squeezed in the toe box to avoid cold feet. Recall air is a good insulator. Thus, 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 exotic dancers like Jasmine Dubrow in Independence Day and women in the horizontal profession like Vivian Ward in Pretty Women.
When buying boots look for a classic style with sturdy heel. #OTKboots #agelessStyle Click To Tweet

details of slouchy boots

midlife woman looking chic in slouchy booties
Outfit details: Vince Camuto slouchy boots, GNW tight, Eddie Bauer skirt, striped sweater, Hermes collier de chien bangle, DIY statement necklace (all own) and layering top c/o Adea

How to Style Tall Boots

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 60s. 😉
  2. Unless the 70s are a trend, avoid to wear a midi skirt that covers the upper part of your boots. Well, this look is so 70s. It ages every woman who was already alive at that time. Thus, if you go for the 70s style, keep everything else modern. #agelessstyle #tallboots Click To Tweet
  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 tights – is a cold gap. Thus, make sure to 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. More on styling over-the-knee boots (opens in new tab).

Outfit Ideas for Tall Boots

Here are some outfits with boots for visual inspiration.

#maturefashion lady looking at the shaking ground in Fairbanks during Anchorage earthquake Example slim suede pull-onsover 50 years old woman in stylish slouchy boots Example slouchy

stylist in maxi-skirt with Humter rubber boots Example Hunter rain boots

fashion blogger in sheath, cardigan, high heel boots, tights and lots of necklaces Example with chains and a sheath dress

midlife style blogger Example with midi skirt

fashion blogger in tall boots with boot toppersExample with boot toppers

fashion blogger in tweed skirt, leather jacket, sweater, riding boots, scarf and shearling mini crossbody Example with cable-knit socksover 50 years old style blogger Nicole in autumn colors with leopard print boots Example animal print tall footwear

street chic with aviator jacket, purple sweater, knee length skirt and below the knee studded boots Example studded statement pair

older woman in animal print winter coat, leather beret, boots and jeggings Example riding boots with leggings

over 50 years old blogger in tall booots leather jacket straight skirt Example Euro Chic with with tweed skirt

blogger Nicole in modest womens clothing and knee-high footwear Example statement color with leather skirt

Equestrian Styles Are Timeless

I like to wear my riding boots with skinny jeans, leggings, my denim and tweed skirt.

fashion blogger in leggings with boots Zara multi color faux fur sweater, Sanchez riding boots (all own) and leggings c/o No Nonsense

style blogger looking happy in shoulder-long locks, and neutral color outfit Lookbook Store motorcycle leather jacket, Eddie Bauer straight skirt, Anne Klein scarf, pantyhose, GNW knee high socks, Sanchez equestrian boots, pendant necklace (all own)

skinnies, blazer and riding footwear J Brand jeans, Pippa bag, Sanchez riding footwear (all own), and asymmetric fit-and-flare blazer c/o Lookbook Store

mature style blogger wearing plaid with hounds tooth and equestrarian footwear Long sleeve Tee, Banana Republic hounds tooth skirt, GNW tight, Sanchez riding boots (all own) and Riders by Lee buffalo plaid button-down shirt c/o Walmart

Studs Another Way than under the Sole

When you follow this blog for a while, you know I am crazy about studs. Thus, when I found these Valentio 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.

stylist over 50 in shirt dress with Valentinos Black self-sewn shirt dress, tall Valentino boots, Gucci bag, and Oscar de la Rente silk scarf (all own)
fashion blogger in LBD with tall statement studded boots Black dress with boat-neck c/o Covered Perfectly styled with own leopard print scarf, brooch, head band, GNW tight, and Valentino studded tall boots

How to Wear 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 Choos at the original price tag, are so fortunate! Here two inspirations what to wear with knee highs going out for dinner.

fashion blogger in mini skirt and knee-high footwear BB Dakota sheath worn as skirt, Jeanne Pierre sweater, statement belt, GNW tight, Hermes collier de chien bangle and Jimmy Choo shearlings (all own)
mature woman in winter going out look with tall footwear Anne Klein cable knit sweater, Hallogen tweed skirt, silk abstract floral print scarf, belt, GNW tight, and Jimmy Choo knee-high shearlings (all own)

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.

shoe accessories Dance shoes with toppers c/o Top of the Boots
faux fur top How to add them

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 and 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

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.

You may be also interested in the 13 secrets of how to wear over-the-knee boots over 40 .

How do you wear your tall boots? Do you switch into pumps at the office? Let me know, I am curious.

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Stylish Monday November

My blogging friends and I are hosting a boots linkup party for Stylish Monday November. Everyone is invited to linkup their IG or blog outfit posts. See you and your friends at the party.

hostesses of the stylish Monday boot linkup party

I am joining the Stylish Monday #linkup party. Please join me there and bring a fashionable friend. #letsparty Click To Tweet


Join the Stylish Monday November linkup party here.


Photos of me: G. Kramm

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