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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  1. I turned 60 this year and am about to be remarried on New Year’s Day. I actually just purchased a pair of snakeskin print booties from Aerosoles which I will be wearing with a turtleneck sweater dress and a faux snakeskin moto jacket to my civil ceremony. I am excited to rock this look with my transitioning salt and pepper pixie haircut. I’ve waited my whole life to feel free from the opinions of others… I say do whatever make you happy 😌❤️

  2. 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 🙂

  3. 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.

    1. what Clinton Kelly says is disappointing to me. As I will be almost 30 soon! But, I think it depends on the trend 🙂

  4. 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!

  5. 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.

    1. 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!

  6. 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!

  7. 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@

  8. 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!

    1. 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. 😉

  9. 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.

    1. I think the height thing is definitely an issue in my case. I’m 5’4″.

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

  10. 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?

  11. 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.

  12. 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.

  13. 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! 🙂

  14. 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….

  15. 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 🙂

  16. 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!

  17. 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.

  18. It really has nothing to do with your age (and please, while I’m a few years younger than you, I would prefer not to look forward to “39 the second time” as being an “older woman!”). It’s how you feel (okay, there are exceptions – juvenile fashions should not be worn on adults, but these boots are hardly juvenile). Do you feel good in them? I’ve had people tell me that they could never pull off something I am wearing (in that instant it was one of my fav skirts), and it kind of surprised me. Because I didn’t think I was doing anything “trendy” I just thought I was wearing something that I felt good in and looked nice. Apparently I rocked the look, cuz I had the confidence, not because of any other factors (and certainly not because I had the perfect anything). So, really? How do you feel? Confident? Self-conscious? My advice – Keep wearing them until you make up your own mind for certain. 🙂 You will either grow more confident and embrace it, or you will decide for yourself that the look just doesn’t work for you and leave it behind. 🙂

    1. I’m more than half kidding on the age thing. I do feel more tired than I did at 23, but it may be because I no longer feel invincible. 😉

      And, yes, I think confidence makes a world of difference!

  19. Yes, you can definitely wear these boots! They look great, however, I wouldn’t necessarily pair them with jeans unless they are jean leggings, which would look adorable. These boots would also look great with skirts and tights or with leggings (and a long shirt or sweater.) And you could totally wear any of those looks. You go girl!

    1. Believe it or not, these are skinny jeans that I’m wearing. I don’t think I could get them tighter and still move. ha!

  20. I definitely don’t think you’re too old to be wearing this trend… but I do think that since you’re on the shorter side (like me *sigh*), that these boots seem unbalanced on you… if that makes sense. They seem to “cut you off” at your knees. I don’t know if it’s because of the wide opening at the top, or because of the height, or because of the angle of the photo. Just my two cents. I absolutely think you could wear tall boots, though without looking as if you’re dressing inappropriately for your age! 🙂 I’m just wondering if a different boot would be a better fit (no pun intended).

    1. Yes, I would imagine that on a taller woman, they wouldn’t “take up” so much of the body. They certainly are 1/3 or more of me, aren’t they?

  21. Noting what others have said, I thought I would point out that I think the boots are meant to have a “pirate” flair to them. I recently saw an “older woman” in similar boots with black jeans and a long shirts with ruffles down the front and on the shirt cuffs. She added a vest and looked adorable. But she also looked like she wore this type of outfit all the time. She was SUPER comfortable in her outfit and couldn’t have cared less what anyone else thought. Truthfully, I think that is what makes ANY outfit…your comfort level. I am 45 and I like to wear things that I am comfortable in. I don’t care if it is intended for someone younger than me, I just want it to look good and make me feel good. I often find that there are fashion trends that look GREAT on older women if paired differently than intended. So my advice….GO FOR IT! Wear them until you own them!

    1. Great input. I think you’re right on the comfort/confidence thing.

  22. I agree with others. The length seems fine, but the wide top, I’m not sure about! Maybe it is the sweater with it? Either way, I totally know what you mean that going out of the comfort zone is hard, so good for you for stepping out…and you still look cute!

  23. I would love to see another picture of you wearing these boot with black leggings and a dress. I LOVE big boots and your adorable so you could definitely pull it off, or any look off for that matter. But these particular boots I think maybe would look better with black leggings and a dress or skirt.

    1. I will try that. That seems to be a common suggestion. Will report back later!

  24. I think you look great and you will get used to them once you wear them out a few times. Does your husband like them? My husband likes me in tshirts and jeans which is kind of boring. My kids like it if I try something new. I bet your kids think they are cool boots.

    1. The first time I wore them I got a few raised eyebrows in-house. But, now no one even blinks twice. They are super comfortable.

  25. I’m putting my two cents in on the “these boots might be a bit too big for you” side. In the first picture, I actually thought they were over-the-knee boots, which I think are inappropriate for ANY age. I might also pick brown for you to go with your skin tone – I think the black is a little harsh.
    HOWEVER. You go, pirate! I think the rest of your style is awesome and comfortable. I’m one of those people who judge people’s clothes on the street (as in, that skirt is far too short, or leggings are not pants, or ballet flats are not appropriate for a Chicago winter slushy day), and I would walk right by you thinking you put thought into your appropriate clothing. 🙂

  26. It’s not about age. It is about the fit and attire with it.
    The boot is a little wide at the top. If you cannot get a slimmer fit, you could wear black leggings to give it a more streamlined look. Skirts are very cute. If the top of the boot stills throws you off wear black stockings. It is a great look once you get the fit and ensemble right. If first you do not succeed, try, try again.

    1. I think I will try it with my black leggings and black skirt. Thanks for the suggestion.

  27. 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. ;))

  28. 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!

  29. 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.

  30. 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. =)

  31. 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!) 🙂

  32. 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!

  33. 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!

  34. 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!

    1. 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. 😉

      1. 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!

    2. 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!

  35. 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!!!!!!

  36. 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. 🙂

    1. 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!

    2. 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.

  37. 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! 😉

  38. 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.

  39. 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!

  40. 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.

  41. 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.

  42. 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.

  43. 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!

  44. 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. 😉

  45. 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.