Q&A: Can Older Women Wear Trendy Boots?

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This week’s Q&A actually comes from me to you. I’m asking you for your fashion advice as regards older women and fashion trends.

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A month or two ago, Aerosoles sent me some boots to review. These boots. They are amazingly comfortable, exactly what I expected from the brand, known for its comfort. I love wearing them.

The boots are also on the trendy side. I, as we know, am no fashionista. But, I do like to dress in the current decade when possible. So, I look forward to updating my wardrobe whenever I can.

These boots are also tall. I knew they were sending me tall boots, but I was a little surprised that they were sooooooo tall. They are, indeed, knee boots. Apparently, in my old age, I’m not reading things as carefully as I should.

To be honest, I feel a little piratey. Would that it be Elizabeth Swan I resembled. Or perhaps a little super hero-esque? Mrs. Incredible, maybe?

However, I’ve been observing other women out and about. At least here in Southern California it’s not uncommon to see knee boots. Usually, though, I’m seeing them on much younger women than I. This year I turn 39 (for the second time) and while I’m not ready to relegate myself to “old lady clothes,” neither do I want to dress beyond my age.

According to some of my younger and/or hipper friends, Shaina and Jenn, both claim that these are totally appropriate for someone in my stage of life. As long as I wear something longish to cover my rear and balance the ensemble.

But, never one to be satisfied with a simple yes, I turn to you. What do you think?

Can this old lady wear trendy boots?

Disclosure: I was sent a review pair of boots by Aerosoles. All opinions are my own.

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97 Comments

    1. They are amazingly comfortable. And I love it that they aren’t heels, too.

  1. Let me preface this by saying you look great! I’m in my twenties, and I tend to stay away from trends. Some of them I think just look silly…I don’t care how many people are wearing it. Then there’s the issue of frugality. Say you had to pay for those boots…and next season no one’s wearing them anymore?

  2. 39??? Oy my!! You are WAY too young to question if you are “too old” for something. ; )

    I am nearly 50. I wear all kinds of boots. I love them and I get compliments on them all the time.

    I personally feel that if women of ALL ages dress modestly, classy, neat, tidy and up to date……then they look fabulous!!! Wear the boots with confidence and you will look amazing.

    P.S. Love the boots. Love the whole outfit you have on. You are dressed to perfection….updated, clean, and modest. Love it.

  3. My mom bought me tall black boots that roll down at the top for Christmas. I’m in my mid-30s and was feeling very pirate-like until I bought a pair of skinny jeans. They look awesome together and I feel confident and in style in that outfit.

  4. I think you can totally wear those boots! They look great! I love your sweater, too. I am a 25 year old new mom and seeing you rock those boots gives me hope for my second 39th birthday! 🙂

  5. The boots are cute! But, I had to comment because I absolutely LOVE your sweater! You look great with the trendy clothes. I feel pretty frumpy most of the time and only gave up scrunchies because I recently cut my hair too short to wear them anymore. 😛

    1. I still have all my scrunchies! I’m not giving them up. If I ever grow my hair long enough to wear them again….

  6. yes, you can pull off these boots! just a couple of thoughts – – they look to be a bit too loose around the top, any chance they are a convertible boot meaning you can wear them tall or fold them over for a top “cuff”? i’d suggest they be worn with skinny jeans, leggings or a skirt/dress that is just above the knee in length. a longer top/sweater is totally appropriate. age isn’t an issue – comfort, confidence and the ability to pull the look together is what counts.

    1. The folding over tends to accentuate the piratey-ness. The clerk at the Gap told me that is how she would wear them, though. So, maybe that is part of the trend?

      1. giggle…I took Sonny Boy shopping with me one time (18 year old) because I just have bad fashion sense at times … he told me a few pair of boots were too Pirate-ish … and he was right, which is probably what attracted me to them! Over 21? Pirate look is NOT for you 🙂

  7. Wear the boots if you are comfortable in them. Unlike mini-skirts, they don’t age out. But I agree that skinny jeans or “jeggings” would be the right ones to wear under them. I’m 43 and where I live in the burbs outside of Chicago there are many 39+ women who look appropriate with a tall boot style. Go for it!

  8. Absolutely you should wear them. Just remember with tall boots, it’s best to show as much length as you can between the boot and your waist. So wear them with jeans that are “tighter” on the thigh, not baggy. You also might want to wear a short jacket versus a long sweater, like in your picture. This way there isn’t too much happening around your knees 🙂 I only say this because I got a killer deal on some Anthropology boots this past winter that are the same height. I could not figure out how to wear them and make them look good on my 5’4 frame. Of course, my fashionista 14 year old daughter who now shares my shoe size took them over and wore them. She always looked great. So I just followed her take on them, used my own appropriate to age style and took those boots back!

    1. I’m not sure I could find tighter jeans! LOL. These are skinny jeans that I’m wearing in the pic, but my legs are really thin — from the knee down. Might be too hard to tell in the pic, though.