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?

I’m going to agree with several other commenters when I say that I think they are cute and the length looks great to me… but they do seem awfully wide at the top. Now, maybe that’s for ease when walking since, obviously, your knees need to bend. I don’t know. But I think a slimmer silhouette would be my preference. I have stupidly long legs, so things never seem super tall on me, but I like the concept of a nice high boot! (And I will totally still be rockin’ my red python heeled boots for many, many years to come, my friend. ;))
I agree with Ellen. I’ve been hoping to get some for myself! Apparently you are blessed with smaller calves which makes this pair feel “piratey”. A tighter fit on the calf and a slightly shorter pair should look great on you!
I think boots are great at your age. I’m just a few years behind and I like wearing my boots once in a while.
Like others, I would probably suggest another boot. They look a little big on top. I’m not a fashionista, so you may want to look elsewhere for advice.
Well, we’ll figure this out together, won’t we?
I have seen lots of women older than 40 wearing tall boots at church. They look great in them!
These boots seem a little different, though. They’re quite wide at the top, and they’re taller than the average tall boot I see. Most I’ve seen stop a bit below the knee and don’t have a wide gap at the top.
I think the concept of tall boots is great. I’m not sure these particular tall boots work that well, though.
It’s just my opinion, but you asked for it, so there ya go. =)
That’s pretty much what I’ve been thinking, too.
Oh dear! I am right behind you, so I HOPE you don’t really think you are OLD?! I agree, what you feel good about yourself in, is what you should wear. (And I could probably follow that advice of one commenter who said to go for it and take a risk a little outside of the norm, too!) 🙂
40 seems young to me — NOW! 🙂
The boots look fabulous – primarily because they are on you. It is sometimes uncomfortable to get out of our style comfort zone, so if the boots are physically comfortable and you like them, or perhaps even the idea of them, then channel your inner pirate lass and rock them. Rock them with jeans, leggings, skirts. Someone once upon a time gave very sage advice that is appropriate here: “Age ain’t nothin’ but a number.”. So love yourself in those boots!
Trendy boots yes, although I think a slimmer pair of boots would be more flattering. I would reduce the size of the cardigan (although keeping it past your butt for balance is good) and reduce the size of the boot for a trimmer appearance!
You Rock in that outfit! The boots look great and I agree with the long sweater or vest…it is a must with knee boots in any age. I only caution that the pants MUST be form fitting (like the jeans you have on) or leggings or you get a balloon effect on the thighs above the boots. Very pirate like and NOT PRETTY! Up here in southern Ontario high boots are “in” with long sweaters and scarves. Especially at the arena. For all ages!
So, you would look like every other hockey mom up here and fit right in!
Ha! Love the hockey mom reference! We play inline and so the rink is outside — in San Diego, but I’ll give it a try. 😉
Might want to skip the scarf and touque then if you are outside in San Diego and not at an ice rink in Ontario! 🙂 Might look a little weird!
I agree, it’s less about age and more about wearing them with the appropiate outfit. Tight pants are a must, but that’s why long sweaters work so well for those of us not so much in our 20’s anymore! Those particular boots do look a bit big though, maybe it is just height and width and the top like other suggested. I don’t think its a question of you pulling them off though, you totally can!
They look very nice on you, Jessica! I think you should wear them! This coming from a 60 year old! I don’t think I will ever wear “old Lady clothes!” I wear what I like and feel good in.
God bless, Kathy in Illinios
PS 38 is not old!!!!!!
I know I’m not old. I just like to get a rise outta ya. 😉
I think they look cute. The one thing I noticed that tripped me up was that they seem so wide at the top. I know it’s so hard to make boots that will fit everyone and still look good on everyone…if they made the top smaller, it probably wouldn’t go over everyone’s calves. It doesn’t look *bad*, it just tripped up my eye in the length of your outfit (which looks good together). I wonder if you could attach a small piece of elastic to the inside, making a kind of a tuck? Or the other thought I had would be to fold them down…but that won’t help get away from your piratey look. 🙂 It could still look nice, though. Just things to experiment with.
I think the other ladies are right. It’s not too old for you, as long as you’re not *trying* to dress like a 25 year old (there are some women at my kids’ school that from far away you think they’re 25-ish, and then up close they’re very obviously NOT…ick). You pulled off the classy “older”-woman look with it. Kudos. 🙂
I agree with Carrie. I think the boots are super cute, just a little wide at the top. I think you’d like them more (and feel a little less piratey, lol) if they were snug on your leg. The idea of using elastic to make them tuck is a great one. 🙂
You are definitely not too old to wear a rockin’ pair of boots!
Yes, that is what I was referring to… the “cute young thing” that you notice from afar, thinking she’s in college, and then up close you realize – NOT.
As for the tuck, I’ll give that a try. I think you’re right, they’re a general size, but I obviously have knobby knees that make them look bigger. Thanks for the suggestion.