My Hunt for Actually Good-Looking ‘Lifestyle’ Sneakers

When you’re a Gen Xer who was raised onFree to Be…You and Me, you grow up with the impression that every day might as well be Wacky Outfit Day, and it’s totally normal to wear non-matching footwear. I think that’s what has drawn me to so many of Charlotte Stone’s shoes and sneakers with two different colorways in each pair. (I treated myself to a pair of theirAnto mismatched sandalsthis year, and I love them.) But these sneakers, as adorable as they are, don’t feel great on. It might be a me thing—I have skinny ankles and my heels sit low in shoes, two factors making it so that certain styles of shoes and sneakers don’t hug my foot properly, leading to an awkward fit, and back-of-ankle blisters.

I love the look and color of this low-profile, suede pair. They remind me of the Asics the popular girls wore in college. But there’s not quite enough support in the footbed and heel for me to be able to walk in them for very long. But I very much would wear them for their style, on a day when I wasn’t planning to walk much.

I’ll start with what I like about these: the mashup of ballet-slipper styling with a rugged, athletic-looking sole. The contradiction appeals to me. Also, the Ortholite insole is the perfect combination of springy and firm. It cushions and stabilizes my foot perfectly. It also has padding around the heel so that it perfectly hugs mine. What doesn’t work for me: These don’t move with my foot in a way that feels natural. There’s something about the straps across the instep that makes it an awkward fit. The straps are hard to keep flat, and I became too conscious of them as I tried to walk. Also, the sizing seems off. I’m a true 6.5, and even the 7 is small on me.

This pair of Pumas is a much better fit for me—although not perfect. I blame my damned skinny ankles and low-sitting heels, once again. The tops of these are just a bit too high on me—too high to be comfortable walking in. It’s a shame, because I really love the look of these. They’re at once chic and sporty. I’m really into the silver leather—I own a fair number of silver metallic leather shoes. And the Ortholite insole is fantastic. I want to spend the rest of my life with Ortholite insoles cradling my aching feet. These run small, too, but not as small as the other Pumas I tried on. The 6.5s were too tight, but the 7s worked.

I’ve never been big on animal prints—they’ve always felt too stylistically loud to me—but something about the playful combination of leopard and pinkish terracotta here tempted me to take a step outside of my comfort zone. I think they look really great, and I’d love to make them a part of my fall footwear wardrobe. These sneakers are much more substantial than the other Gola pair I tried, in terms of a supportive footbed and insole. However, they feel a little heavy. I think I’d get tired walking around in them for too, too long. So I’d save them for short-distance days.

Style-wise, I find there’s not enough going on here, so these don’t quite meet my fashion needs. (I wanted to try the more interestingCecily Mary Janesbut they weren’t in stock.) But function-wise, these are incredibly comfortable and light. I could probably walk from one end of Manhattan to the other in them, without a major arthritis flare-up. The insole is supportive, the back is contoured with padding to support the ankle and heel, and you can just slip your foot in without unlacing and relacing—which is nice, because my hips and lower back sometimes spasm when I bend over to put my shoes on. (Aging in a human body…sigh.)

I find these to be so classically stylish, with an added bit of whimsy via the woven heel, and some nice contrast from the tan seam. They looksmartto me, but also a little bit funky—the kind of footwear I can wear to a business meeting, or to go out at night. Thanks to the “SkyWeave™ Cushioning System” these happen to also be quite light and comfortable. I love the way they both look and feel—although the platform makes them a little high for me. Still, I can see walking for miles in them, and possibly never wanting to take them off.

These aren’t exactly sneakers, but I’ve had my eye on these other Cole Haan Oxfords for some time now, and this silver leather iteration is my favorite. I love the high/low merging of serious shoe styling with a sneaker bottom—the best of both worlds, stylewise and comfortwise. They’re at once chic and whimsical—and they feel great on. Light. Bouncy. Supportive. I want to live in them.

I am a freak for green. It’s the color I default to in almost everything (the exterior of my house, my entire kitchen, so many of my clothes), to the point that I often have to ask myself, “Are you sure you want yetanotherthing in your life to be this color?” I just adore the emerald satin on these Reeboks, and they would coordinate well with so much of my green-forward wardrobe. The whole sleek look appeals to me. And despite their low profile sole, these are wonderfully supportive, while also incredibly light.

Oldstersubscribers keep recommending the Vionic brand to me in comments onposts about the achy feet and jointsthat seem to be an inevitable part of later life. Now I know what they’ve been talking about. Vionic incorporates some proprietary features—”Vio Motion™ Technology” for greater balance; “lightweight EVA midsole”; “One Plant™ Sustainability Standard”—that taken together make this a comfy, supportive, stabilizing sneaker/walking shoe hybrid that’s also not too heavy. Style-wise, I love a neat, white leather sneaker with a bit of black detail—a chic neutral of shorts. Also, the name, “City Walk,” is perfectly on the nose in terms of what I’m looking for.

Maybe this is a good place to mention that I just bought myself afree-standing closetto store all my shoes and sneakers. (I’ve been knownto collect them.) Which means that maybe there’s room in there—and in my wardrobe—for stylish gold leather sneakers, too? Why not? These are amazing—attractive basics made a bit special by metallic leather, and a great feel. I only recently started wearing the FitFlop brand, and I find everything they make to be the perfect combination of orthopedically sound and good looking. They boast an “ultra-light, all-day cushioning Anatomicush midsole” that hugs your feet and allows for easy, comfortable movement. These are a lot lighter than they look.

The lightest pair in the bunch, these are among my favorites. They’ve been following me around the internet for some time, and I’m glad I finally got to try them. These SeaVees remind me of my first pair of Nike Cortez—the white nylon ones with the red swoosh and blue stripe in the sole, which I got in the summer of 1978, a few months before I turned 13. I loved those sneakers so much, I’ve searched for decades for a pair that would feel equally airy and bouncy, and also be just as cute. I might like these even better because of the earthy terra cotta color, perfect for fall (or any time, given my status as an “autumn”), and the lack of sports-related insignias. They also have a useful tab in the back that helps you pull them on. When I tried these I was so pleased with the way they look and feel, I couldn’t help but wear them out that night. I felt like I was walking on air. (And three people atUnicorn Barcomplimented me on them.)