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?

You can totally carry off the high boot look!!
My MIL is in her 50’s and wear knee high boots all the time. She looks great. So i am sure its ok for you to wear them. I say if u think it looks good and you feel great in it then it doesn’t matter. Because you have to feel good in something to feel beautiful too 🙂
I don’t have time to look through all the comments, so here is my two cents. I think these should fit you around the calf. They look to big. If they fit you I think they would look best with leggings or skinny jeans. The best advice I heard about dressing your age was from Clinton Kelly on the TV shoe the Chew. He said 30’s can do 75% trend, 40’s can do %50 trend and 50+ can do 25% trend. That’s my new rule.
what Clinton Kelly says is disappointing to me. As I will be almost 30 soon! But, I think it depends on the trend 🙂
What would 25% trend be? Like a pair of trendy boots?
I think they look great on you! I wear tall boots a lot. I am 35 years young so I think they work! lol
You are so cute! Just wear what you want and don’t worry about what others think!
I think those boots are absolutely great for your age just as long as you avoid wearing them with a hoochy-mama skirt. I suspect you own no such skirt so I think you are good to go.
I wonder if google can tell me what a hoochy-mama skirt is… 😉 I think I know what you’re talking about, and no, I don’t think I own one. Ha!
Uhhh…heck yeah! I probably wear things that a 47ish lady should not be wearing (skinny jeans?) but figured, who cares, I LIKE it and I refuse to be aged based on what I’m wearing. Hubby sometimes rolls his eyes but he knows it my way of saying I’m still YOUNG. I pretty much gave up the mini skirts (mostly because my legs got a little more fluffy) but I refuse to wear them below my knees … so I say bring on the boots Jessica!
As a costume designer people are always asking me questions about what to wear and what is age appropriate. My answer is always the same: Wear what you like and feel good in; Wear what fits well (don’t look at size look at the mirror for fit) ; Look in the mirror before you leave the house (look at the total overall look does it come together) ; and if you like what you are wearing, most everyone else will…you will just send out those vibes. I am not big on rules, but if you wear what you like and are comfortable in it, you will probably look good in it too.
PS I am upwards of 50 and would totally wear these boots@
Costume designer! We need you!
I am 38 years old and here is a picture of me in my tall boots, http://snailpacetransformations.com/2012/02/24/thrifty-fashions/ They are not as tall as yours but I would love them even more if they were. I think you pull them off wonderfully! and with style and grace!
Aww, thanks for your kind words!
YES we can wear trendy boots! I believe boots truly were made for women our age (we’re almost the same age — I turn 40 next month). They’re extremely flattering and I feel we walk with more confidence in them. At least I do. 🙂 I agree with some of the comments about the leg opening being a tad wide for your petite legs (yes, I said that — you are slender). I might fold those down to see how that looks. For myself I prefer just a bit more of a heel nowadays but I will say that I used to have a pair of Aerosoles boots with about the same heel — I literally wore them out, because they were so comfy, especially for walking all over San Francisco.
BTW, you might be able to put on a pair of leggings with those!
They are probably the most comfortable shoes I own, so I will be looking at the brand more closely from now on! As for skinny, yes, from the knee down! I think I need to buy a Thigh-master. 😉
I don’t like boots tucked in pants on anyone. I think they look best with a skirt. Most people are not tall enough to pull off boots with jeans.
I think the height thing is definitely an issue in my case. I’m 5’4″.