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Hot Boots for Fall and Winter: Women Over 40 or 50

boots that are cute for older women

by Christina Gregoire

There are lots of options for boots this fall, so older women (over 40, 50, or 60) will have a great time finding fun footwear to update their old outfits. 

Just remember to be a bit practical.  Flat footwear is best for walking long distances, chunky heels and wedges are more stable than spiked heels, and extremely crazy trends look best on teenage girls.

Other than that, I'm giving you permission to wear whatever you like, so there’s no reason you need to play it too safe with trendy boots.  You don’t want to look boring and dowdy before your time, do you?

Boots Are Hip for Fall

hip trendy victorian bootsEven if you are required to dress conservatively for work, you can trick out your everyday look with a cool pair of new boots.  Well, don’t be meshugenah and wear fringed booties if you work in one of the “big four” accounting firms, and don't wear punky, spiked boots to your tennis-club gig.  But, within reason, any older woman can find cute footwear with trendy details that won’t make her look like she raided her granddaughter’s closet.

Tall Flat Boots

Tall boots with a flat heel go with almost everything.  I first started seeing this type of boot in Europe during 2009, but the trend is still in style on the continent, as well as in the states.  Elegant women of all ages look extremely chic wearing tall boots with midi dresses and long skirts.  (If you want to wear a knee-high boot with a mini, I recommend adding tights that match your boots.)  And, most older women look fabulous wearing skinny jeans, leggings, or jeggings tucked into a pair of tall boots.  Some of my favorite new and trendy details include:

  • Boots with buckles or little buckled straps that wrap around the boot. (When packing, put these boots in bags so the buckles don’t snag your clothing.)
  • Boots with thick soles in contrasting colors.
  • Boots with an outside zip (where the zipper is on the “wrong” side of the boot).

70’s Style Boots

There are many remakes of boots from the 1970s.  One example is the knee-high, burgundy boot in the main photo above.  It has a nice, thick (easy to wear) heel and a small platform sole.  You can wear this boot in all the same ways that I recommend for tall flat boots.  The only difference is that you need to make sure you get a boot with good cushioning.  Everyone raves about “Cole Haan air” boots, but you can find less expensive brands (like Sofft) which have good footbed cushions.

Some of the newest boot styles have huge platforms straight out of the disco days of yore.  If you want to wear them, I won’t stop you; however, I have sprained my ankle wearing huge platforms (twice) when I was in my twenties, so hang onto a railing when going down the stairs.  However, a small platform is wonderful because you can wear a higher heel and it won’t feel as high because of the design dynamics.

Another 70s style is a clog boot, which has a wooden sole similar to those ubiquitous Candies slides we used to wear with jeans.

Boots With Laces

I’m not sure where this trend comes from.  It’s related to work boots, army boots, and Victorian Steampunk (which I’m really starting to love).   However, you can find laced boots to go with every trend you can think of.  I’ve recently seen:

  • Lace-up rainboots (wellies)
  • Lace-up mid-calf suede ankle boots
  • Lace-up high-heel ankle booties
  • Lace-up biker boots
  • Lace-up high-heel work boots

Wedge Boots

Wedge boots are available in every imaginable shape this fall.  You can find everything from an imperceptibly subtle, low, hidden wedge, to a crazy, scary, sky-high wedge, like this 5-inch wedged bootie that should only be worn by women married to orthopedists.  However, don’t be afraid of wedges.  They are usually very stable and are a good investment for women who want to look a few inches taller without falling over.

Short Cowboy Booties

Cowboy (well, cowgirl) boots never really go out of style, but these days there’s a different type that’s a bit more like a bootie.  No, these boots are not practical for hiking out in the rattlesnake-infested desert (because your calf isn’t protected from a bite), but they are cute with jeans.

Some short cowboy boots are worn folded down, and I think this trendier style looks best with skinny jeans; however, other cowgirl booties are fine with dresses or skirts.  You’ll have to use your good judgment when putting your outfit together because I only wear cowgirl boots when I’m somewhere like Arizona or Colorado.

I know how hard it can be to find hip clothing that fits you once you've hit “a certain age.” So, shoes and boots are an easy way to update your worn-out style.

No matter what kind of boot you are looking for this fall, it’s out there... and then some.

More Articles for Baby Boomer Women:

How to Wear Ankle Boots With Skinny Jeans, Leggings, or Shorts - Older Women

23 Trendy Plus Size Clothing Sites for Large Women Sizes 1x - 12x

How to Wear Leggings if You're Over 40 or 50

Best Sites for Women's Travel Wear: Wrinkle Free Clothing

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Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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  1. Rev.Angela Chester

    I like every outfit shown with burgundy color for fall and winter,
    I'm 5'3 inches tall and 148 lbs, and I think I could wear these
    Styles and colors well,thanks for the idea's. I am a Minister,
    And at 61, I still like looking stylish and feminine conservatively,
    When out and about, and I think all of these outfits will look
    Great with leggings, I will admit I've been shy of wear leggings,
    Being a Preacher, what do you think?

    • Tina

      Reverend Angela,

      I think you would look great in leggings. Just make sure the top you wear is long enough to make the outfit conservative. God made you cute/feminine for a reason - to help you connect with people and to spread his message.

      Tina Boomerina (AKA Christina Gregoire)

  2. Jacqueline Dingle

    Great advice for 60 somethings !
    Just what I needed to regain confidence on how to wear skinny jeggins with the right boots.
    Your webpage helps to make mature women feel youger and up to date

    • Tina


      Thank you so much for your comment, Jackie. Boomer women can wear almost any style if they give it a few tweaks. I'm glad to help. We're all in this together.

      Tina Boomerina (AKA Christina Gregoire)

  3. Jean Marie

    Curious if you'd give a thumbs down on boots that are motorcycle type/engineer type boots like Gianni Bini "Jordan" or Dolce Vita "Solvae." Since they hit mid-shin and are loose fitting at the top, I think I'd look too boxy in them. Or maybe they're just for young women. What are your thoughts? Thanks!

    • Tina-Boomerina

      Jean Marie,

      Personally, I think those boots would be cute if you're tall enough (or proportional enough or have the right body / style) to wear them. I just looked at both styles and I think the Jordan style is perfect for just about anyone. And, if you think you look good in the Solvae style, do it.

      It's YOUR body. It's your money. If you're unsure, ask your kids... or someone like that. They'll tell you the truth.

      Tina Boomerina

      • Tina-Boomerina

        ps I think those boots would look best tucked into skinny jeans (or jeggings over a tunic top if you like comfort). Unfortunately, I have no experience with those boots because I like to pretend I'm a few inches taller than I am... so I wear heels unless I'm at the dog park. But, those boots are cute.

        Also, there are no fashion police. Actually, I sent them all to Orlando to enforce my no-shorts rule for people over 30 at Disneyworld.