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.
The narrower toe here makes this otherwise classic biker boot quite wearable.
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.
Low-slung and clean-lined, with cool leather detailing in the place of hardware.
A sturdy-but-minimal under $100 option.
I love multiple straps, but it’s a look that can overwhelm very easily. This option manages to come off nicely sophisticated.
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.