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. You’re rocking those knee boots! They look fabulous. Unless you’re planning on wearing them with hot pants (which I know you’re not), wear ’em! They’re definitely not too “young” for you.

    1. Maxi dress, mini skirt, now, hot pants. I’m giving google a work out trying to figure out what everyone’s talking about! 😉

  2. I think they look great on you. We are the same age and I know what you mean. I don’t even have a clue which section of the store I should be in, since I don’t feel the teen stuff is right yet I am not ready for a sweatshirt with birdhouses on it either! LOL I love your sweater too, you are fashionable. I should not be giving fashion advice though since I only recently quit matching a scrunchy to my outfit. I do think those boots would also be great with black tights or leggings and a skirt and long sweater for winter next year.

  3. Oh my dear Jessica,
    Older women? Really? You’re on your second 39th birthday and you wonder if you can wear these lovely, perfect, fashionable boots in which you look lovely, perfect & fashionable?!

    I have no question about the boots or your wearing them. You look great!

    But – “older women?!” Dearie, I just celebrated the 20th anniversary of my second thirty-ninth birthday (do the math or not, as you please) and I still don’t feel like an “older woman.” Why would you?

    But, alas, I do not wear knee boots. Being less than tall and slender, I would look like a kindergardener in her over-sized rainboots bought to last her through second grade…

    You look stunning! Go for it.
    Emma Ann

    1. Ha! Well, I’m more than half joking about the age thing. I don’t think 40 is old — anymore! But, it seems like 23 was just yesterday!

  4. Yes, you can wear them!!! They are cutest with a skirt (knee-length or just above). Tights are optional depending on weather.

    I got my first pair of tall boots this winter and I have lived in them, at my ripe old age of 35 🙂

    1. Do you think knee length skirt would look okay with these boots already at the knee? Trying to figure that out.

  5. Not that it matters, but you look much younger than 39. I don’t think age has so much to do with it as feeling comfortable with what you wear.(within reason of course). And why do you have to cover your rear? I think they look great. I am older than you and I have several pairs of knee boots. I always get compliments.

  6. Jessica, I think they are really cute on you. I’ve seen many women our age rocking the knee boot look. I have a pair, too and I wear them with jeans and a maxi dress.

    Like Kate and Carrie, I believe it’s how confident you are in them. If you where them confidently, no one will question your age. (Unless, of course, you’re running around in a mini skirt, no stockings and knee boots — then you may get some raised eyebrows no matter how confident you are! Not that you would ever wear that particular assemble!)

    ~Blessings on this beautiful Tuesday

    1. I’m going to have to look up the current definition of mini skirt! I have a few shorter skirts, but I’m guessing that the term is relative. LOL What was mini when I was in 8th grade is probably no longer “mini.”

      1. I am positive you do not own a “mini” skirt. According to my daughter (who has a very questionable idea of appropriate clothing) a mini skirt barely covers your unmentionables.

  7. I think it’s all about how confidently you wear them. I’m a 27 year old elementary school teacher, and I feel like I don’t “dress with the times” because some things (like knee boots) are outside of my usual wardrobe. I know several teachers in their 30s and 40s, however, that wear them proudly and look fantastic. Most importantly, as Carrie said, everyone else is more concerned about how they look themselves. If they’re comfortable then go for it. I think you look great!

    1. Well, “dressing the times” is an interesting topic. Thankfully, there’s a wide range there, otherwise…. scary thought!

  8. You know, Jessica, I’m not sure it’s the age as much as it is getting used to wearing something that you don’t normally wear. The Hubby gave me two very nice pairs of boots (one a little taller than the other) and it took me all winter to be totally comfortable walking out and about in them. They were SO outside of what I normally wear – but I loved them. And I finally realized that no one was looking and pointing at me when I left the house because they were all worried about what THEY were wearing. 🙂

    So here’s the bottom line for me – if they are comfortable, decent (not talking about shoes, but other clothes), and make me take a little “risk”, I’m willing to give them a try. If you’re comfortable, who cares what some stranger on the street might think? GO FOR IT! I think you look great (you rock the Elizabeth Swan look), and the sweater is perfect with the outfit.

    For the record – 40 isn’t old (all four of my siblings are well into their 40’s and 50’s – not that I don’t give them a hard time for that, of course! 😉 )

    1. Yes, I think you’re right about the comfort level. As for old, I’m more than half joking. 😉

  9. I think those of us no longer in our “early adulthood” can totally rock trendy boots. I live in an extremely conservative area of the North East and wear boots nearly everyday. A couple pair are tall and flat the others are slightly lower and healed. I love them and the fact I feel slightly more dressed up. I get complemented often and sometimes told ” I wish I could carry that off”. My general response is,why can’t you? Even at 39 (which I will be this year) I think we can wear the skinny jeans and boots and make them look good! Many of my friends do as well.