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Fashion Boots for Women Over 40, 50, 60 – You Can Never Have Too Many Boots!

how many boots do you need? older women

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We all know that money is tight, but you don't want to buy something that's going to make your feet hurt or that's going to hurt your feet long term. So, if you're spending a lot of money, look for investment-grade boots in investment-grade styles that are similar to these:

  • Fendi Yorkshire Buckled Suede Knee Boot: boots for baby boomer older womenOoh La La, this ridiculously expensive (over $1,000) boot has everything I love: suede to help it mold to your foot, buckles to bring your style up to date, and a thick, rubber heel to help your balance when stepping onto escalators.
  • Stuart Weitzman Toujours Boot:  This sleek boot has an incredibly sexy EuroLook that will never go out of style.
  • Miss Mooz Shannon Boot: Take the trendiness of Victorian style, add some height, and camouflage the heel, so that you'll look naturally taller... beautiful genius.
  • Uggs Fabrice Boot: I usually don't like Uggs on older women, but this style would be fabulous with skinny jeans or jeggings... or a skirt and some tights... or a pair of jeans... or a boring travel dress... or...

In reality, older women (like you and me) look better when avoiding trendy extremes.  We look better embracing subtle details like the 1970s-retro heel on this Diane von Furstenberg Suede Chunky Heel Knee Boot from several years ago. I like this type of thick, stubby heel for both boots and shoes.  And, this boot is great for two important reasons:

  • The heel is solid and stable.
  • The suede will stretch to fit swollen feet.

Cute Boots for Real Women and Real Lifecute boots for older women

Real women who want good solid boots should check into styles like these - or something similar - for reasonably priced boots:

  • Nine West Tiptop Boot: This has no heel, but it has beautiful EuroStyling that will work with skirts and jeans.
  • 7 for All Mankind Floriane Bootie: If you can wear this, get it. It's a reasonable price for a boot that will take you from breakfast through dancing to the blues at some old club.

How to Build a Boot Wardrobe

If you are just starting up your boot wardrobe, get a pair of versatile knee-high black boots and a pair of knee-high beige boots. Both should have solid, stacked heels and insoles with great cushioning. Buy these basic boots in the best quality you can afford; you will be wearing them for ten years or more. (If you wear pants or jeans most of the time, you’ll only need one pair of knee-high boots in black.)

Next, get knee-high or ankle-high flat boots to replace those ugly Nike-style white sneakers or loafers or flip-flops that you always wear. After you have some basic boot styles in your closet, copy the well-dressed Europeans and look for amazing boots in colors you love.

You would have been astounded by how many striking, elegant Parisian women were wearing all-black winter clothing with bright red, mustard yellow, or cobalt boots. So, go ahead and have a little fun this year.

More Articles About Boots for Baby Boomer Women:

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

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

Hot Boots for Fall: Women Over 40 or 50

What Are the Best Wide-Calf Boots for Women?

What do you think of this article? Leave a comment at the bottom of the page.

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. Miriam

    how do you keep your jeans or leggings or whatever tucked in with shorter boots?

    • Tina-Boomerina


      I must have short legs or long leggings and jeans. Sometimes, I tuck my leggings into my socks. They also have something called boot socks with cute prints (tiny repeating prints) and I've seen models in magazines wear those so that they come up above their boots... but I've never tried that myself. My short boots come up to my ankles or above, so I've never had a problem. I've read that rubber bands work, but that might not be very comfy. Also, you might need boots that fit tighter in the ankle.

      Anyway, I wear my husband's socks or I wear those knee sock nylons and scrunch them down. If none of these ideas work for you, please let me know and I'll ask around. Maybe you need "tall" sized leggings if the socks don't keep them in. As for jeans, I don't wear jeans because they are not comfortable and I'm 61... and I've paid my dues with tight clothing... so I think I deserve a break after wearing all the crazy trends over the years. However, I just read that these same tricks work for skinny jeans. Hope this helps. If you're still having problems after trying socks and all the other ideas, you either have the wrong boots (too short or too loose) or your leggings/jeans are too short for your long legs. But, let me know if you need more info.

      Tina Boomerina

  2. nancy

    I am 73 years old, slim and want to know I can wear boots and not try to look like a young girl??

    • Tina-Boomerina


      The secret to wearing boots and not looking like a young girl is to go with suede and not leather. If you happen to have a short bob, you can wear a heel up to 2 to 3 ½ inches. It’s best to wear a straight skirt just past your knee, but if you want to go a little above your knee, you can wear dark tights to cover your knees. An oversized A-line coat never hurts.

      Another fun fall look is to do the equestrian style. Wear tan boots (with a low or flat heel) and jeans or leggings that tuck into your boots. Wear a tailored coat or a black, high-neck sweater with a blue scarf knotted around your neck.

      Thank you for your question. You have inspired me to write an entire article dedicated to this concept.


      Tina Boomerina

  3. Lori Grantzinger

    Wherecan I find the cadigan showen tin the piture with the artical,boots with slacks and jeans. I have the boots and loved the sweater

    • Tina-Boomerina


      Sorry to say that the cardigan is from Hobbs UK 2012, when I first wrote this article. Sometimes I update my photos, but that outfit is from 2 years ago. You can try Hobbs to see if they have anything similar.

      Tina Boomerina

  4. Helen

    can I wear a over the knee boot at age 66

  5. Tina-Boomerina


    About a year ago I would have said no, but they are so popular now that I have to say, "It depends."

    I would not wear those over-the-knee hooker boots with the stiletto heels. In my opinion, if the whole outfit is put together right, so that the main focal point is NOT the boot, and you are wearing a flat boot over jeans, I think you could pull off wearing over-the-knee boots.

    I can't see your outfit, so I would get a second opinion from someone honest like your daughter. However, I can imagine a hip baby boomer chick in over-the-knee boots. I suppose I should write an article that explains the right look.

    If you play with different pieces, I'm sure you can come up with an ensemble that looks put together, with a bit of class, but also with a fashion forward edge. You might want to get some inexpensive boots to try out the look before going high end. However, if you like the look and people respond well to it, an "older" woman almost always looks better in "better" clothing and accessories.

    Send me a pic if you feel like it. I promise not to publish it or comment on it. I'm just curious.

    I've been wondering about that style of boot for a long time.


  6. Lynda

    can women over 60 wear jeans tucked in boots

    • Tina-Boomerina


      Sure. I do it all the time. Well, I don't like most jeans so I tuck my jeggings into my boots. Hey, I'm going to add you to my newsletter. If you don't like it you can opt out. Look in your junk mail, but I just sent one out today. I won't send another for about a week (or maybe less). Who knows....


  7. Lisa

    I like the article, but wondered why you would have young models posing for an article about women over 40...

    • Tina-Boomerina

      I use young models because I get those photos for free. Alternately, I could use the underexposed/overexposed/out-of-focus photos that my husband takes of me.

      I think I'm using the lesser of the two evils. If you want to volunteer and send me photos of you or your friends in boots, I'll use them.


  8. Annie Lin

    Is a 69 year old woman too old to wear jeans tucked into her boots. She's 5'6" and wears size 6 jeans.

  9. Jerene

    Please add me to your newsletter list. I'm 61 and fashion challenged. I just bought some cute ankle boots and don't know how to wear them. I also saw that tall boots are okay. But, what do I wear with them? I don't wear dresses very often, mostly slacks and jeans.Don't have any leggings. Should I get some? I sure don't want to look like an old lady trying to be young. I just want to look confident and put-together.

    • Tina-Boomerina


      I'm about two months behind in answering comments. Sorry. I'll try to get out a newsletter sometime in the next year. I promise.

      I only wear jeggings because they are more comfy than jeans. If you can fit into jeans and slacks without the buttons busting off, you're fine in slacks and jeans. Well, it depends on what you're wearing. If you like tailored jackets and things like that, you're fine.

      I'll email you... two months late... long story.