See 9 great ways how to wear tall boots

mature fashion Alaska winter outfit

Tall boots are an Alaska classic outwear

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. Given that the cold season can last from mid September to early May, I have invested in a timeless collection of boots as I am a skirt/dress kind of gal.

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.

How I wear my tall boots

Equestrian styles are timeless

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

#fashionover40 woman in leggings with boots Zara multi color faux fur sweater, riding boots (all own) and leggings c/o No Nonsense
#fashionover40 skinnies, blazer and riding footwear J Brand jeans, Pippa bag, riding footwear (all own), and asymmetric fit-and-flare blazer c/o Lookbook Store

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.

#styleover50 woman in shirt dress with Valentinos Black self-sewn shirt dress, tall Valentinos, Gucci bag, and Oscar de la Rente silk scarf (all own)
#fashionover50 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!

#fashionover50 mature woman in mini skirt and knee-high footwear BB Dakota sheath worn as skirt, Jeanne Pierre sweater, statement belt, GNW tight, and Jimmy Choo shearlings (all own)
#fashionover50 woman in winter work outfit 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

I also like to switch things up by wearing boot toppers. I wrote an entire post on how to look mature when wearing them. What I love about them – besides the style factor – is that they add extra insulation. It is so needed when you wait for the bus outside at -20F (29.8oC).

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

You may be also interested in how to wear over-the-knee boots over 40 or secrets to look great in them.

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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P.S. Adrienne at The Rich Life in Wine Country and Jill at Everything Just So feature various bloggers in their monthly “How I wear My” series. This month’s theme is How I wear my tall boots.

Photos: G. Kramm

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