Your Fall Shoe Conundrums.

Your Fall Shoe Conundrums

Your Fall Shoe Conundrums

A few weeks ago on Instagram, I asked you for your biggest shopping conundrums and questions. Far and away, the biggest question was around shoes! Below the shopping grid I have laid out your questions (and my answers). This was fun to work on; I hope it was helpful! I am definitely feeling lots of flats and lower heels this season. And I love that kitten heels (and Mary Janes!) are on trend this season. I hope 5″ stilettos never come back in style, my feet and back are definitely happier than they have been in previous seasons!

Your shoe requests and questions!

Shoes for fall that aren’t heels!

I actually feel like this season’s best shoes are not heels! In fact, I just ordered these Toteme flats, I think they are so effortlessly stylish. I am also loving a mesh flat or a mary jane flat (these from Anthropologie are just heaven on your feet!). And of course the mesh flat phenomenon. I have and love this pair from Khaite (mostly sold out everywhere at this point; worn here) but I love these as a more affordable and available alternative. For fall, I am very very into this simple black pair!

Boots to wear with non-skinny jeans or dress pants.

I’m doing either this pair from Madewell (the kitten heel feels fresh this season) but also love this kitten heel style. I’d also recommend something slightly western like these! I also love this pair from Toteme. I think the main note here is that we want an almond or oval toe, with just a little heel.

Shoes that go with dress pants

I am digging a sharp, pointy toe slingback. It feels more up to date than a pump and I generally can’t do a mule (my feet won’t stay in – I say generally because those Loeffler Randall bow flats I used to wear every day worked for me, but nothing else does… but also, if I were a mule person I would be all over these Manolos!). Two that I really love are these from Jimmy Choo and these from Toteme. I also really love these textured pumps.

Flat snow boots that don’t look hideous

Oh gosh, this one took me a while but I do like these? Or the brown color. I do not miss dressing for snow.

I’m looking for chunky flat boots! Sort of like sleek combat/ the row zip style or similar 

How about these, these, or these?

Comfy stylish waterproof boots

I would go for a chunky rubber platform boot like these. Or these from above!

Mary Jane flats you can actually walk around in! 

I have and love this pair from Anthropologie. They are like a hug for your feet. At a more luxury price point, I am crushing hard on this pair from The Row but for now I think I’m sticking to something more affordable… I feel like Mary Janes are a little bit trendy so not something I want to invest in. And I also really love these from Chloe. I can’t speak to them being easy to walk around in as I haven’t tried them on but they look great!

Perfect loafer and updated bootie

We tackled booties above but I love these loafers! I’ll also be getting a lot of wear out of my classic Gucci loafers. They are several years old but get better every season. I have heard amazing things about this pair from Freda Salvador, I have not pulled the trigger… yet.

Shoes to walk to work in! (Essentially chic sneakers under $200 that I can walk up a hill in) 

I would do the J.Crew loafers! They are very comfy.

I’m trying to decide if the Birkenstock Boston is here to stay! Thoughts?

Oh yes absolutely!!! Definitely, 100% here to stay.

Comfortable/put-together shoes that aren’t sneakers! (like a cold-weather version of the gold birks!)

We’ve listed a lot of really comfortable and put together shoes (any of the flats I mentioned would work) but since you said gold birks I’m going to say silver loafers!

Disclosure: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature things I truly love here. Thanks for your support.


Leave a Comment

Leave a Comment


  1. Hannah:

    LOVE ALL OF THESE! I recently bought a lovely pair of the Madewell “Lacey Ballet Loafers” in Timber & they will be perfect with a pair of skinny or straight legged jeans.
    For boot cut-I have a 2 pairs of Frye ankle booties (a pair in brown & a pair in black).

    9.18.23 Reply
    • grace at the stripe:


      9.19.23 Reply
  2. Shana:

    those Jimmy Choo’s are so.pretty!! saving to my wish list 🙂

    9.18.23 Reply
    • grace at the stripe:

      Aren’t they great!? I love.

      9.19.23 Reply
  3. m:

    The struggle is real! I’m still trying to find jeans I actually like so that I can start shopping for boots to go with them. Until then, I’m in whatever jeans I have with driving loafers, because they’re comfortable and classic. I feel like a rich, unbothered Connecticut housewife whenever I wear them.

    9.18.23 Reply
    • grace at the stripe:

      I hear you! But “rich, unbothered Connecticut housewife” is not a bad vibe!!!

      9.19.23 Reply
  4. Jessica Camerata:

    I have SUCH mixed feelings about these mesh shoes. But I am 100% team silver shoes. Already have two pairs and trying to think of every excuse to wear them.

    xo Jessica
    an indigo day

    9.19.23 Reply
    • grace at the stripe:

      Honestly I felt the same and then I put on a pair and never looked back. They are magical!

      9.19.23 Reply