Saturday 6th June 2020
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Tough (enough) boots

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I very much dislike stories in magazines and online that attempt to place age-based deadlines on women for wearing particular articles of clothing and accessories. Real life, after all, is much more of a case-by-case proposition. And the fact that we are all such tough critics of what we see in the mirror makes us—and not some unseen arbiter—the best judges of when it’s time to move on from miniskirts, say, or skinny jeans. I got away with high hemlines until suddenly, at 47, they started to look not so much unflattering as silly on me—like I was a grown woman dressing like a little girl. And I gave up my snub-toe Frye harness boots when I moved last winter—they hadn’t made any real sense in my wardrobe since 2004. Still, I’ve never lost my taste for a boot with some degree of clunk and at least the hint of a badass vibe. Take, for instance, this quite subtle option from Madewell: that one leather strap at the ankle says a lot, but so quietly.

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The narrower toe here makes this otherwise classic biker boot quite wearable.

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A nice, somewhat equestrian option for if you only want to go just the tiniest bit tough. They are also under $125, which is nice.

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Low-slung and clean-lined, with cool leather detailing in the place of hardware.

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sturdy-but-minimal under $100 option.

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I love multiple straps, but it’s a look that can overwhelm very easily. This option manages to come off nicely sophisticated.

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Metal harness rings don’t feel grown-up enough to me anymore. But the one here is covered in leather, which should come off cheesy but is actually totally genius.

Posted on November 3rd, 2014 27 Comments

27 Responses

  1. Helen says:

    Speaking of boots, can you do a spot on low-vamp booties? I hate shoes/ boots that cut me off at the ankle, and it’s really hard to find a nice bootie w/ a low vamp in front so it looks flattering w/ skirts or slacks. Thanks.

  2. sarah says:

    Interesting bit about the Frye harness boots. I recently have become obsessed with them– for some reason I didn’t ever buy them back in the day– but have been wondering if, at 50, that shoe-ship has sailed. Thanks, I guess, for some perspective. 🙂

    • Tammy says:

      I, too, have been eyeing the Frye harness boots for the past couple years. I wear jeans three-quarters of the time, and even though I’m three years from 50, I’d like to find a quality boot that will have a cool vibe. And Frye has that quality factor I bought a pair of pointy-toe Zara boots that I adore. The pair is much more comfortable than I anticipated.

    • Linden says:

      I love my Frye harness boots — no one will ever take them away from me, including me. I bought them to wear while horseback riding, and they are excellent for that purpose. I also wear them when I’m going to spend the day walking in San Francisco, because they’ve never given me a blister and they protect my feet from impact on the hard city streets like nothing else. Beautiful and functional.

      • y.k. says:

        same here – i love my frye harness boots, they are – unlike anything else in my wardrobe – pale seafoam green -perfect w/ faded jeans. i get them resoled & polished once in a while& they’re very nice.

    • Mamavalveeta03 says:

      I see Frye Harness boots as a classic: Kind of like Coco Chanel on Budweiser.

  3. hannah says:

    Truly appreciate the “not unflattering, just silly” line; it perfectly describes how I feel about the flippy-skater-skirt thing happening right now.

  4. Yes, thank you. I really want to slap people who tell me, “You’re too old to wear _____”. For me, a black boot like these is an essential.

  5. Great boot picks. I love my mid-calf (on me) moto boots from Burberry, they are just tough enough for this fortysomething. I did feel a little off when I wore my doc martens last winter after rediscovering them in my closet. I don’t think I can part with them yet, but I probably won’t wear them again.

  6. c.w. says:

    I purchased last week the Via Spiga Bara boot.

    I’m in my sixties––am I too old to wear them?––hell no. And I wear them with skinny jeans. Snap.

  7. Freda says:

    Enough with the age appropriate mentality.

  8. Freda says:

    The frye boots are appropriate for anyone who wants go wear them.

  9. MarlaD says:

    I think biker boots are all age appropriate, it’s what else you’re wearing with them, and that is kind of dependent on where you live. I am in my late 50’s and last winter when I was living in Santa Fe, I wore them with tights and pencil skirts and felt jaunty and appropriate. Right now in CA that look doesn’t feel right to me. In my old age (lol) I’ve developed arthritis in one foot and those boots are pain free so I’ll figure it out!

    I have a friend who is tall and willowy and in her 70’s and wears hers with jeans and they look great on her. c.w. up there is right on with those Via Spigas.

    • Peggy says:

      What is the name of the biker boot you wear? The reason I ask is I am quickly approaching 50 and have arthritis in both my feet but it is definitely far more advanced in one foot. My favorite short cowboy boots have worn out after only a year and I miss them plus for me they are just practical for the midwest winters. Thanks!

  10. joannawnyc says:

    I have Frye harness clogs that I’ve loved and worn for the past 10+ years (starting in my early 40s). I find I don’t really avoid things for age reasons so much as BTDT reasons. Or, yk, health reasons (arthritis is, alas, a factor now).

  11. DelawareDeb says:

    I just returned from two weeks in Europe to include 3 days in Paris, and wore a boot similar to the Alberto Fermani “tough.” Mine hit right below the knee, and I tucked in my black or charcoal skinny jean and kept outfits simple with a scarf. I never once considered myself too old (at 60) for the boot or that the boot had too much going on. Plus, those boots were totally functional for walking and walking and walking over cobblestone.

  12. Meg says:

    Love the LD. Tuttle choice. I like a quieter look with a heavy outsole.
    Just bought Vince style Yale ankle boot. Looks great with everything

  13. Ellen says:

    Great boot post.

    I also love my Frye Harness boots and I currently have then in gray, black, and brown. I fell in love with them 10 years ago, and are perfect (sturdy with a cool vibe) for New England falls and winters. I have a bad back, so the combination of the heel height and support are an added bonus for me.
    I am not ready to give them up yet!

    Short skirts are also long gone for me – I am 43 and short, so they started to look off on me a few years back.

  14. Katie Lynn says:

    I’m in a search for a motorcycle boot with an almost Western edge (replacing a beloved pair of Borns), and I’m really surprised at how few boots have tread on the bottom this year. Most have a smooth bottom, or at best a slightly ridged bottom. But no nice hefty tread. If I were to attempt to wear the smooth bottomed ones I’d be on MY bottom half the winter. Snow and ice are slippery!

    • Rachel D says:

      You could always have a shoe repair person apply a rubber sole. I’ve done this with several pairs of Fryes.

  15. Mamavalveeta03 says:

    The Madewell biker boot is so appealing, but a high instep is a curse! I always need a zipper…or a good Chelsea boot.

  16. Anne says:

    Love, love, love the bikers from J Crew, I’ve been wearing them pretty much non- stop since they arrived on my doorstep. Also in heavy rotation are a pair of Chelsea boots by Frye and a wedge chukka that look like they would cause pain, but are so comfortable that I can walk all day and not even notice I’m wearing three inch plus heels.