It’s no secret I’m not a die-hard sneaker girl. I only own two pairs: Play CdG x Converse sneakers (enter to win a pair!!) and nike running/walking shoes, and I don’t even wear those very often. But in keeping with my desire to go a bit outside my comfort zone leading up to my 41st birthday, I’ll admit I’m willing to try a wedge sneaker, or a high-top. I don’t generally like either, except for the Isabel Marant bobby style (because you really can’t tell there’s a wedge in there, and I love the suede), and now the Eileen Fisher wedge sneakers which Sarge in Charge has got me helplessly obsessing over…
1 Shoes like Pottery low-top sneakers | $155 at Steven Alan
2 Eileen Fisher wedge sneaker | $250 at Eileen Fisher
3 Tory Burch Miles Perforated Sneakers | $165 at Shopbop
4 See by Chloe suede and leather sneakers | $395 at Forzieri
5 Comme des Garcons Play X Converse sneakers | $75 at Azalea after code GRECHEN25 for 25% off
When the weather’s cooler, I love the look of sneakers and jeans, boyfriend or skinny, or sneakers and leggings, and even sneakers and skirts. I can actually picture myself wearing the EF wedges with leggings and a giant sweater. How cozy π I’ve not always loved them on me, but I like the look of a woman in sneakers if done right – it’s that easy-chic aesthetic I love.
What do you think? Do you love sneakers? would you do a wedge sneaker?
Click through for TONS more of my favorite sneakers for fall…

Fabulous post! I love sneakers, tennis shoes (comfort shoes!). Of course, all the sneakers that I like above are from Barney’s .. lol $$
Monica.
i know, they’re SO EXPENSIVE. only in my dreams…but it’s nice to dream, no?
those TB slip on’s are great for down the shore walking the docks or going to the beach – i SO need those now!!! – and i’ve been dying for YEARS for a pair of golden goose sneakers or boots!
Grechen, love this post. I always love it when your OOTD includes those CDGPxC sneakers with the heart. Adorable.
More importantly, I am now smitten with the Eileen Fisher Zest Wedge Booties (yes, I actually went and looked them up – $250, available 8/20. I NEVER pay full price anymore, but might make an exception for these amazing booties – seems like they would go with everything! You’re right, with leggings and a big sweater would be adorable, and probably with tights and a skirt, too.
As for sneakers, I have several pairs of Simples that are amazingly comfy and cute. One thing I like about Simples is that they don’t make my size 10 feet look massive and they are really cushy. I used to wear them as part of my work uniform – Citizens Elson or Joe’s Skinny Visionnaire jeans, James Perse or Garnet Hill tee, Inhabit cotton or cashmere cardigan, lightweight printed scarf, fun Smartwool socks and Simple sneaks. That got me from October – April in Chicago, and I bet I wore that at least 3 days a week!
Now that I think of it, I really miss wearing sneakers and will be happy when the weather turns. Thanks for the reminder.
love those TBs!! and don’t even get me started on golden goose, the sneakers are insane. but i’m not sure i could EVER pay that much for tennis shoes!!!
i’m going to have to try simple, you’ve mentioned them before…
and the eileen fisher booties are so awesome. i’m in love, but after trying on the splendid wedge booties at nordstrom today, i don’t think i can rock that look. my calves are still just too big for high-top shoes π i didn’t love the look on me right now, but maybe i’ll grow into it!!
OMG, you just reminded me of a pair of Simples I had for years and LOVED. Completely forgot about them. And yes, they did have some magic power to make big feet look relatively small. My sister and I have noticed the same thing with our classic white Vans sneakers, too.
Grechen, if the booties make you feel bad about your calves, they are not the shoes for you! I have been glad to see you breaking out some new looks that show off your legs. Don’t regress, just skip the wedge booties…for now! π
Sarge in Charge, don’t you love that the Simples use recycled tires for the soles and hemp or recycled fabrics whenever possible? I also love the fun laces they sometimes include as an option. They are definitely not for everybody, but honestly, they are the cutest of all the sneaks I’ve tried for my Amazonian feet.