Style Advice Q & A

Knee High Boots – Can You Tuck Jeans In?

Hi Deborah,

I’m a size 4, athletic, fit, and 42 years old.Can/should I wear skinny jeans tucked into knee-high boots?

I know it’s very “in” now, but I’m wondering if it’s okay for the over 40 crowds. I often look good in youthful clothes, but I’m unsure if I should wear them. I don’t want to come across as wishing I was still 22.

Thanks, Carol

Hi Carol,

Yes, you can tuck your jeans into your boots and look Fabulous after 40! Wear skinny jeans or jeggings tucked into tall, flat boots to look current. Flat boots are sporty.

It’s tricky to tuck skinny jeans tucked into tall, high-heeled boots. You can look dated or like you are trying too hard. If you want to go this route, choose a tall, plain boot with a chunky, not a fine high heel. A chunkier high heel looks more sporty with jeans.

I prefer to wear high-heeled boots and wedge boots with skirts and dresses, not jeans.

Deborah Boland tall boots with jeans

The best flat boots to wear with jeans are leather riding boots or suede flats like these gorgeous merlot ones!


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10 thoughts on “Knee High Boots – Can You Tuck Jeans In?

  1. I think it’s sad that a woman would fear that something as simple as tucking her jeans into her boots would be considered too young a look… it’s also a shame she feels she would have to be a certain weight to pull this off. I am 46 and a size 0-2, but I would still wear boots tucked in jeans even if I weren’t. I notice this site focuses a lot on thinness; maybe that is why….. I think you’d have more readership if you wouldn’t.

  2. As an over-50 woman, I often feel unsure about age-appropriate styles these days. I want to look good, even trendy sometimes, but not matronly or like I’m trying to dress too young. So I timidly bought my first two pairs of skinny pants this weekend. The knit pair looks great with a tunic top and coppery flats. No problem there. The slim black jeans look pretty darn good, too, with my black flat-knee boots. But that was where I was worried that I might be trying to look too young. After seeing the picture here, I think I am ready to try it out. Thanks for the excellent advice!

    1. Hi Laurie,
      Way to go!!!! YEAH!! It is hard to make a change and venture out sometimes. Especially after 40 or 50 or 6o… it can be tricky to know if we are dressing “age-appropriate.”
      It sounds like you are on the right track, so enjoy!!! Great to hear that our info is valuable!

  3. I love the pikolinos boots in the picture but don’t see that style on the websites I searched…what are they called, and who sells them?

    1. Hi Terri,
      We wrote this post a while back, so they are probably long gone. However, has a great selection, and you should be able to find something similar! Good luck; a great-looking, updated pair of boots is the absolute hottest thing to have in your closet this season!

  4. I think the thigh-high boots look too pirate-like and are best left to twenty-somethings. For some reason, they also remind me of 70s-era hookers. LOL. To each her own. I love tall riding boots tucked in jeans, however. I’ve been wearing that look since my 20s back in the 90s.

  5. Yes, Yes, Yes! I think boots are ageless, especially with dresses. I saw an 80-plus woman with a killer figure (yup- killer) wearing great boots with a dress.

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