Privilege Blog

Affordable, Trompable, Comfortable – Riding Boots Are The Thing


There’s an eternal appeal to riding boots, don’t you think? Immediate visions of moors, fog, and hair swirling in the wind? Your hair, a romantic stranger’s, long-maned horse, no matter. So what if the closest grassy knoll is a berm by some suburban train tracks, or, what’s an imagination for?

So when Naturalizer contacted me about this little project, I was interested. “Style our Jersey boots,” they said. “And then we’ll post the pictures on our Facebook page and you can represent Bloggers Over 50.” At least that’s approximately what they said. Here is the official announcement. Note that the additional pairs of shoes I would win – if my outfit gets the most votes – would be then given away here. To you guys.

“Voting will be open until Wednesday, October 30th at which point the blogger with the most votes will be selected as the winner of 2 additional pairs of shoes from Naturalizer’s fall line. During the contest, we’ll also select 5 random Facebook voters to win a pair of Naturalizers of their own!”

All right then!

In an era of color mixing and patterns, which although I do minimally I see everywhere, riding boots seemed to demand A Return To Black. But what clothing silhouette would work with both the boots and my shape, at 57? I haven’t owned tall boots since the 1980s – they were slouchy, skirts were full, and I was not yet 30. So we start with a little analysis.

The Jerseys are casual boots, somewhere between rubber wellies and Italian leather. They probably aren’t fully waterproof but they’re certainly not delicate. They zip up, and stretch at the top of the calf. The rubber sole makes them comfortable as heck. In other words, perfect for tromping across fields or wet fall city crosswalks.

How to wear riding boots if you're middle aged.

As such, they call for pants, more specifically skinny jeans tucked right into their shaft. But I don’t wear skinny jeans.

However, I do have an Anthropologie skater dress, which you may remember from its disappointing outing with moto boots. Aha! And, from the depths of the Drawers That Remember Everything, I dredged up a pair of Alice and Olive leggings, bought years back in a They Will Be Perfect For New Year’s moment. They weren’t perfect, by the way, but no matter.


I tried on hosts of jackets for this outfit. My first thought was to finally find a use for the Kiton cashmere. Didn’t look great. Back into The Closet That Remembers it went. Then maybe the ol’ Chanel? My secret non-honorable agenda there was thinking that perhaps the display of the iconic tweed would win us the Naturalizer contest. But the shape was wrong, wrong, wrong.

So, on to the Isabel Marant √Čtoile heathered black tweed, add a family diamond and pearl bar pin (because a Return To Black does well with white or clear jewelry), Vicente Agor Ice Shelf earrings (again, clear), and an ancient black Coach hobo, or bucket bag, or whatever we’re calling it these days, that had been hiding in the closet. Clutching my red reading glasses in one hand, as one does.

Then I stepped back, and saw that at 50, absent architectural white hair and vivid red lipstick, an all black outfit works better with a little color at the face. I pulled out the Etro scarf my brother gave me 5-10 years ago, chock full of colors that don’t let me down. Thank you foggy sea blue, and my friend lavender, your efforts are duly noted.

And off to the moors we go. Or, to Facebook, to see what other bloggers in other age groups did with the boots. And perhaps win a pair for yourself.

Thank you as ever for all your support.


Update: I won! Thank you everyone who voted!


(BTW, Etro scarves are beautiful, and live forever, as far as I can tell.)


Naturalizer Blogger Challenge Image

36 Responses

  1. Beautiful boots, great outfit.
    Really you need to try skinny jeans with a tunic-y top or nice long sweater.. Tuck those skinnies into the boots. It’s a great easy look for a cold day. Even better, nice warm leggings tucked into boots and topped with a cozy sweater. You CAN do it!

  2. Great looking boots. You look terrific, too. Too bad about having to be on Facebook to vote. I’d vote for you if I could.

  3. They are lovely and I know I sound like a broken record but I love your hair.
    I have two pairs of Hermes jumping boots which I still haven’t broken in – they are hard work.

  4. That’s a good style for the skater dress. Although it’s not scandalously short, it’s full and swingy. What if you had to bend over – Paris, France, Underpants would be on display. The leggings solve that problem nicely.

  5. Love everything about your outfit! The boots are terrific. I wear boots all the time. My favorite fall/winter footwear. I wear them with slim cut jeans, not skinny, and love the way they look. (I’m pretty straight up and down with not much hip or waist definition, so it works.)
    I hope you win..I’ve voted!

  6. A great outfit! And I’m seriously considering the boots for myself. But I’m afraid I try to avoid Liking on FB, so I can’t help out there. I suspect you’ll do very well, though. Proud to have you representing for us, we women of a certain age!

  7. Love the outfit, you always teach me something new each fashion-oriented post! I have a pair of Ralph Lauren black riding boots and I honestly adore them (though I keep forgetting to resole them into something more sturdy!)


  8. LOVE the outfit, your hair, the boots… It’s all super! I read your blog faithfully, although I rarely comment (well, I do comment to myself, but not in print) and find that you are an inspiration in so many ways. I’m 65 but haven’t developed as lovely a style as you have. But I do keep trying!

  9. I like this silhouette – and a pair of riding boots that look smart & can go off-roading, that’s always a good thing. And, I think that you COULD wear skinny jeans. You have a fabulous figure.

  10. I love it all!
    I especially love the thought that you put into this terrific outfit Lisa. The leggings are perfect too.
    But I just went on to the Naturalizer Style at Any Age FB page link, and there is nothing posted there.
    I want to vote for you. Any time!

    1. same here! … you have to “like” the company’s page to get to the page where your and the others bloggers photos are.

  11. I have very similar boots, bought in Florence after a weekend spent looking in almost every shoe-shop window we passed. Deri jokes we went to Florence to buy boots.

    Anyway, I love them. It has been raining here and getting to pull out my winter boots has significantly made up for the autumnal grumpiness. I usually wear them with pleated wool skirts but am always looking for new ways to wear them (I am too short, really, to wear them with anything but very short dresses and have never got over the idea that jeans tucked into boots is a look for Puss in Boots). Reading this I realise I am missing the right jacket for my outfits (I usually wear them with a coat), so thank you!

  12. Eschew FB like the plague, but you’re tops by my vote! Thanks again for helping me grow the cojones to grow out the hair.
    Yours is gorgeous and mine is too :)

  13. I have voted for you – good luck! I can’t wear skinny pants either. They are not flattering on me at all. But you look great in your outfit here, and honestly, I think you look great in the skinny jeans post too.

  14. I think you look fabulous in this outift and would vote for you if I did FB but, alas, I do not have anything to do with it. Hope you win though!

  15. Really cute outfit. I only wear tall boots with dresses/skirts, even though I do wear skinny jeans. Just too claustrophobic feeling with pants in LA. I’m trying to vote for you, but don’t understand how to delete the tweeting thing at the moment. I will try again in the morning when I’m less tired.

  16. Hurray! At long last, I chose the same piece of clothing that you did. I have the Anthro dress, which I wore on cool days over the summer. But over boots and leggings… thank you! What a fabulous outfit. Instead of a jacket, I’ll probably wear a longer Margaret O’Leary cardi. Off to buy the boots, which I’ll never win. But I will also vote for you on FB.

    We worked for the same company (I Oracle, you Sun, which merged) at about the same time. I now have 2.5 years left with a startup that just went public. Those options=my retirement. It would be nice if a significant other were to come along, and you’ve inspired hope/dreams, but… one must first take care of oneself.

  17. I love your story of putting the look together. Try this, no, wrong shape, try the next–no wrong length, etc. I often have a look put together in my mind, only to find that part of it is off, not working and go through the same process of trying different options on and discarding. It’s an exciting day if I get it in one go. It’s such a comfort to find out others do it as well. Love the final outfit.

  18. I just voted. It took a minute to figure out how. Ignore the Tweety thing. Then, fill out the information and look at the line that says Blogger—scroll down to find Lisa’s name.

    I love how you styled the boot! The skirt, the tights, the jacket, the scarf, the handbag. Just perfect for these boots and your age. Great Job!

    1. Thanks. And thank you everyone for jumping through the Facebook hoops. I wholly understand the motivation of those who don’t want to.

  19. Love it! Think you can wear the boots under straight legs; they do not have to be only worn with a tucked in pant.

  20. Boots, that ” try ” to imitate real riding boots and are called ” riding boots ” (
    every brand having its own version ), are driving me nuts!

    Riding boots are boots, worn when for riding. It is quite impossible to walk in them for longer distances.

    Please, someone, come up with a correct word for the imitation ones.

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