It’s the time of year for … new shoes.

Casual flats, warm enough for the colder months, comfy enough for all day every day, cute and not orthopedic of you please.

Oh, and if they could be compatible enough with socks, at least so they don’t look dumb if I wear them with unobtrusive socks and long pants, that would be greaaaat.

It’s getting too cold for sandals. And some days you don’t want to pull out your boots. And I’ve taken the SAHM’s no-clunky-athletic-shoes-except-at-the-gym pledge. (I just made up the part about the pledge.)

My pink Minnetonka mocs worked pretty well for the past year. But they’re showing their age. I’m not sure a professional cleaning would be cost effective, or effective at all. Plus they have absolutely no support.

A cute pair of sneaks could work. I don’t think I’m edgy enough (*snort*) to wear those slip on things that used to be just for grandmas and toddlers but are now what all the cool kids are wearing.

Or even keds. Keds just look like grandma shoes on me. Especially with socks.

Okay everything looks worse with socks.

I think I’ve written about this at least once a year.

My yearly shoe dilemma.

What are your feet wearing these days?

23 thoughts on “It’s the time of year for … new shoes.

  1. Verily just put out an article about ways to style sneakers (sorry, dont know how to cut and paste on this thing). I like the way people wear them even w/ dressier clothes- though I’d feel silly trying to pull it off! But yes please to comfy footwear that socks can be worn with!

  2. I agree that the stylish sneakers are the way to go!! I wear Converse, but Lizzie’s right that they are pretty flat. I used to own a pair of Nike’s that were unbelievably comfortable and looked great, so I might recommend that brand for comfort and support.

  3. This is a dilemma I share! I’m wearing Toms now but they DONT look good with socks. Cold weather is coming and socks are about to be a must. I found some brown casual booties last year at DSW that were cute, flat, and slip on. The brand was MIA. They have some life left for this year. What about clogs? I tend to shudder at the word, but Some ppl pull those off.

  4. I wear Sperry’s most in the fall with jeans. They don’t look horrible with socks as long as there are pants on. 😉 Other than that… I basically suck at shoes. Sperry’s all year (socks or no) unless there’s serious snow on the ground. Flats to work, unless there’s serious snow on the ground. LL Bean moc slippers at home. Real fashionista over here!

    • This is totally a problem that I never thought about until leaving the South for the frozen Midwest tundra. Last year wasn’t a problem w/me on fellowship – could just wear waterproof boots when the ice & snow (shudder to think that it’s coming) covered the ground. Now that I’m teaching again, I am desperately trying to find something that will work. So, Catilyn, what do you wear w/serious snow on the ground? Do you do the snow boot to work & switch in the office thing?

      Laura, PLEASE do a follow-up post to this one if you find a good winter shoe!

  5. While we have a Converse store at the outlet down the street, I’ve heard they aren’t particularly comfortable/supportive. I’m partial to slip-on Clarks these days. I love that you can wear them with or without socks and they are super comfortable. You can usually find them on ebay for a deal (or sometimes at the end of a season at a store like Macy’s).

  6. And the Clarks are much trimmer in style than Danskos (and cheaper too). You can also find them called mules on ebay.

  7. Okay, I’m here as your all wise ever knowing little sister and fashionista (obviously … not). Anyway, I third the sneaker comment. Not only because Kendi and Verily and Kate Wyman ❤ and everyone else is doing it, but because I love the look and I think you'd rock it. Also! I have not seen people mention yet (but I'm sure they will eventually) that you could totally wear them with tights and your skirts/dresses too. Tres cute. Anyway, I personally have dookah for these:

    And I think you could totally channel the vibe that the Verily article ( was talking about. No where close to the SAHM chunky sneaker offense.

    But please, please, please … avoid the slip on sneakers. I know Shana's doing it, but some things are best left on Shane and only Shana. 😉

    ❤ Me

  8. I use a pair of Minnetonka Moccasins around my house and a few different pairs of Mary Jane style flats when I go out. I wear long skirts full time so I don’t do sneakers unless I’m doing yard work or something. I’m also trying to branch out and try different pairs of boots when I find ones that are affordable. (I’m not a mom yet but I’m doing the stay-at-home-wife thing, so I totally get the whole “clawing out of frumpdom” thing!)

  9. No one wears basketball shoes unless they’re at the gym on this side of the pond. If you want to go with cute sneakers try on some Pumas. I’ve had mine for at least three years now, and they are soo comfortable. Although, I guess that means they may not make any like I have anymore . . .

  10. I found a great pair of b.o.c. (made by Born) at DSW…they’re clogs. I know! Clogs! But they have a back so they don’t make it feel as bad. When I go abroad in the winter/fall (which is often), they’re the only shoe I bring – I wear them with tights when I’m wearing a skirt and they look fine with pants and socks too. Mine are waterproof, so I can slog through whatever.
    They’re not as expensive as Danskos, especially if you get them at a discount store. I got them in a bright red and wear those and my black hunter boots exclusively when I travel places cold (since it’s not here) or when it’s wet here (which is often). They’ve never leaked and I’ve never slipped, plus I don’t HATE pictures of myself in them.

    I prefer them over cute sneakers because a) I hate casual apparel and so sneakers will never be my thing, and b) they’re waterproof and that’s a requirement for living in a swamp.

  11. Pingback: Movies I’ve watched, sneakers I’ve ordered, and what I’ve been into | This Felicitous Life

  12. Okay, I really really like my BOC (Born Concepts) leather clogs as well as (don’t cringe) a newer pair of danskos. Those are my winter staples with jeans and pants and when I wear skirts it’s all about the boots. 🙂 I’m probably terribly out of fashion at this point but I really like them. I’m not saying I won’t try the canvas sneakers look, and noticed that all the college girls are wearing them… but right now I like my BOC clogs and leather flats.

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