No. 40

Comfy shoes for the sneaker pilled

God, it is hard not to just wear sneakers every day. I started wearing ballet flats in the 6th grade, I remember the silver sheen, the grosgrain ribbon tying a neat bow at the toe. When I lived in Manhattan, I wore sky-high heels on the subway, to a job that had me running all over town. After which, I would prance across the city to meet a friend somewhere that required standing for another 4 hours. I told myself I would never be part of it: the classless masses who valued comfort over style, who showed the world with their footwear that they just couldn’t be bothered: they couldn’t handle pain, they had no resolve. They were terribly pedestrian.

The general attitude towards sneakers has shifted drastically since then, and my own opinion softened along with it. I wear sneakers all the time, so do most of my stylish friends. But the problem with comfort is that once you experience it, it’s damn hard to go back. This, dear reader, is what happened to me.

As a San Franciscan and self-proclaimed lover of the outdoors, I try to weave in movement to every day. Sometimes, it takes the form of a hurried workout class squeezed between meetings and social engagements. Sometimes, it’s an hour long walk on a phone call with a friend. But unless the day is centered around physical activity, I don’t necessarily need to put on my spandex and sneakers.

Yet I’ve found, particularly since the pandemic, that I dress for this movement, if I have any planned for the day at all. This habit has developed well beyond footwear: I find myself slipping into a workout set with athletic shoes if I have a brief walk and talk scheduled with a friend. And yes, the hills in San Francisco are no joke, but a hiking getup does not a casual walk require.

So what are we wearing for footwear so that we don’t have to slip into our well-worn (though cute!) sneakers every time we leave the house? And before I get into some options, I want to highlight that I don’t (still) have a problem wearing sneakers with some regularity, when used as both a practical and visual tool, they can be extremely effective! I want to focus more on the moments we WANT to have a different shoe to wear: maybe the pants we’re wearing don’t look good with sneakers, or we need for whatever reason to add an edge of formality to our look. Sneakers, in my advanced age I have determined, ARE good! But they’re not the answer every day. Let’s talk about some other shoe choices that we can reach for in those moments that will be, dare I say, nearly as comfortable as wearing sneakers.

0-50 degrees

Baby it’s cold outside! Let’s start with an easy one, the good news is that sneakers usually aren’t a good fit for weather under 40 (that’s Fahrenheit for my international friends) and usually we can find our outfits are more evenly visually weighted with boots. Though perhaps obvious, I’ll take any opportunity to talk about boots I love right now. The trick with a sneaker-replacement boot is for it to have enough of a heel not to make you look (and feel) flat-footed, but not so high as to be uncomfortable. I find the sweet spot to be around 1-2 inches high.

Khaite booties with a bit of western wear detail on the toe.

Toteme booties that I bought from The Real Real, and they lost, and then I couldn’t stomach paying 4x the price on brand new ones. Alas, they’re still absolutely perfect.

During a cold winter day, I tend to opt for a bootie, though these Massimo Dutti boots make me want to reconsider putting a skirt on with my puffer.

50-75 degrees

This is where things start to get complicated: isn’t this temperature range just PERFECT for throwing on your favorite sneakers with jeans or pants, or even a skirt? Most boots feel too heavy, and sandals will freeze your toes right off. What’s a girl to do? The trick with replacing sneakers is buying colors you already see in your wardrobe: when you reach for sneaks, is it usually a bright pop of color? A neutral? Stick with that color palette, it’s likely to feel more familiar and fit in with the rest of your wardrobe more seamlessly.

Mary Janes with a strap are so comfortable, they have all of the allure of a ballet flat with none of the deep, cloying discomfort. This Jenni Kayne pair is delightfully feminine.

Hyova for something a little more off-the-beaten path.

AEYDE in a perfect fondant brown, and a little more dressed up for work or dinner.

Larroude for when you have a long day walking around a European beach town.

What makes most heels (even low heels) so uncomfortable? In my experience, it’s the heel! When we keep a low heel and ditch the back, kitten heel mules can be extremely comfortable for walking long distances. Take, for example, these well-priced Madewell mules in a lovely washed denim.

Jacquemus bringing some sculpture, elementary-style.

Emme Parsons with a perfect heel for comfort and playing dress up (either with a dress, a skirt, or denim)

Jamie Haller loafers because you know I love them, comfortable and chic! And yes, I believe that most loafers should in fact be textured.

And don’t sleep on cowboy boots, especially when paired with shorts or a mini skirt! Love this pair from Bobbies. Shorts and sneakers are super cute, but so are shorts and cowboy boots (and it adds a little bit more visual interest!)

75-100+ degrees

I’m assuming you live in a city, is that right? Well, the problem with living in a city is that much of our sandal wardrobe isn’t quite appropriate for traipsing around town. I love my Oran sandals as much as the next girl, but they’re a bit too, close to the ground, shall we say. There’s a bit of a formula when it comes to appropriate sandals for city walking.

Schutz sandals that STRAP. YOU. IN. They even have a bit of a lift to keep you away from the dirty summer ground, ew.

Prada slides are a fantastic choice for something slightly more elevated than sneakers or flip flops, but still comfortable with a very slight heel for arch support.

Jamie Haller with more straps! These may not have the slight platform / heel of the other two options, but the straps will keep you locked in.

Good luck and happy trails!