Footwear On My Radar This Fall

I got a new pair of the same style of Mary Jane shoes for school each September for more years of my youth than I care to remember. My wide feet made anything else impractical. One year they were red, the next black, then they were navy, followed by brown…you get the idea. It was painfully boring so once I grew into my wide feet, I went in search of interesting shoes.

My feet are still wide and plagued with more problems than just width these days, but that doesn’t keep me from enjoying what’s new, so long as they are comfortable.

So let’s talk about shoes and some wearable trends for fall.

Kittenkitten heels worn by Jennifer Connolly of A Well Styled Life

These are certainly not new but they’re back in a big way. A kitten heel is technically a short skinny stiletto with a feminine vibe. The micro kitten is on my must find for fall list. Their heels are as low as 1″ which is what makes my feet happy these days. These kitten heels are 2″ heel and my go-to for dressy occasions. I’ve worn mine with or without the removable bow on the back and found them easy to walk in. Now I’m not talking about a day of shopping, but they’re great for dinner out, a wedding, party, or the theater.


Also on my radar are these Booties with a 1 3/4″ heel and a cushioned footbed. These Tweed pumps have the same 1 3/4″ heel and cushioned footbed. Wear kitten heels with anything you’d wear a high heel with. Their delicate shape is particularly flattering with skinny pant legs, skirts, and dresses. These classic slingbacks have a 1 3/4″ heel and will always be fashionable.

Animal Print BootsJennifer Connolly of A Well Styled Life wearing leopard print booties and all gray outfitell Styled Life

Animal print is popular on everything this fall and footwear is no exception. My favorite is faux aligator and crocodile print. I’m looking forward to bringing out these gray leopard booties this fall, (lower heel version) because they add a nice pop to a neutral outfit. Snakeskin is hugely popular in footwear this fall. These Blondo waterproof booties are 60% off, which is pretty amazing at the beginning of the rainy season.


I love the cut-outs on the shaft of snakeskin booties worn with white jeans on A Well Styled LifeI’ve been wearing these around the house for hours at a time to be sure they won’t hurt and think they will be winners for me this fall.

Square Toes Jennifer Connolly of A Well Styles life wearing squared toe mules and casual outfit in neutralssses

My square, wide feet are very happy to see this trend coming back. Yes, a pointy toe helps lengthen the look of your leg, but squared toe footwear helps shorten the look of your foot. You’ve seen me wear these many times because they’re super comfy. These beauties from Everlane have such a great combination of details. The circular heel is low and a great contrast to the square toe. The crocodile texture is on-trend and a timeless classic. This suede bootie by Sarto has a nice low, block heel so it will be stable to walk on.


I’ll be keeping my eye out for more comfy shoes this fall because several old favorites have simply bit the dust. As I like to remind my husband, shoes and clothes can and do have an expiration date based on how worn out they look;)

Will you be trying any new trends in footwear this fall?


  1. sandra beaty says:

    Thanks for the post. I love Vionic shoes but their offerings are so lame lately. Would you write a post on casual outfits to wear with leggings? I don’t want to look like I just left the gym, but want to still wear comfy black leggings. Thanks for considering.

    1. I love black leggings with a textured tunic sweater and booties. They also look great tucked into knee boots.

  2. I’m in the WWWide foot sizes with so much foot pain, injections in the neuromas, high arch, wide toe box, narrow heels, high arch. I have my dearly beloved Grandmother’s feet. People try to fit me with shoes and then look so astonished. Really? I told you!!!
    Then my podiatrist (who I might kinda almost worship) told me about this simple foot stretch. In 2015, we went to Italy for 3 weeks and I spent the whole trip in pain. After doing these stretches, we went to Italy for 4 weeks and I’m in No Pain at all. It’s a miracle. Every day I do these.

    I still wear wide shoes, Naots, Birkenstock, New Balance. But I feel great.

    1. I’ve just started exercises for nerve pain in my ankle. No luck yet. I’ll check your exercises out. Thank you for sharing!!

  3. Lucretia Roletta says:

    Love the Everlane croc square toe shoes. I think it might take awhile for a comeback of this look.I liked the silver ones that you have been wearing. I detest snakes and can’t wait for that look to subside! The animal print look is a look I’ve always loved but it is way over done now.

    1. I agree the animal print trend is pretty intense these days. It will swing back into balance soon

  4. Yay for the return of square toes!

  5. Angela in NZ says:

    Hi Jennifer
    None of the links to Instagram work. Either page not found or blank page. Have also tried direct through Instagram. 🙁

      1. Angela in NZ says:

        Still a blank page. And I get the same through my Instagram account too.

      2. That’s so strange. What is your Instagram name? Let me check from that angle.

      3. Angela in NZ says:

        My instagram is puhoi_river

      4. Please try again. I think I found a glitch and fixed it.

      5. Angela in NZ says:

        Thank you so much for the fix 🙂

  6. I am at the age where comfort comes first and feel myself blessed if I can find a pair of shoes that have both comfort and great looks. I love the snakeskin and the leopard. Love my leopard boots.
    I’m Not going to buy kitten heels because I just can’t justify spending money on dressy shoes anymore because I’m in retirement so no places fancy enough to dress up come to mind. We dress pretty casual here even for church. A skirt or dress looks fine with flats and a lot safer than heels.

  7. I had polio as a child so my shoe progression was from a total leg brace to ugly, built-up, lace-up shoes, to finally being able to wear a shoe with either an ankle strap to keep it on, zippers, laces, or angled like some clogs so my toes are pointed down. I love to see all these new styles, and have tried many, many styles over the years, but usually struggle with rubs, cramps, and sore spots here and there no matter the shoe or style. Fortunately I am now retired but was a high school science teacher for 30+ years so I was on my hurting feet many hours every day. I guess I relate all this to say we ladies are fortunate to have the many shoe choices which are available to us …even if we have many issues.

    1. That sounds so painful, Celia. I’m sorry you struggled like that. We are very fortunate and shoes have come a long way.

  8. I share the narrow foot version of this story. We had the choice of lace-up oxfords or buckle-up Mary Janes, in black or brown. I chose the black Mary Janes with a double strap. That was it, all through elementary school. And that is why I became a shoe aficionado as an adult.

    1. Anon, too says:

      I am also in this camp. I grew up in a small town with one shoe store and limited choices, especially for my narrow feet. This could explain why I have too many shoes now, though I still need straps to keep the heels on.

    2. We are so shaped by these experiences as a child. I do love shoes.

  9. Cathy Cunningham says:

    Love the snake skin booties. ❤️

  10. I had a similar childhood only my feet were extremely narrow. Every year we made a trip to the same specialty shoe store for the same Mary Janes! Mine were always brown or black. Boring, but practical. My feet are still narrow, but I can usually find shoes to fit. I’m thrilled that kitten heels are back as I’ve never found wearing higher heels comfortable and I’m already taller than my husband.

  11. I immediately fell in love with the snakeskin booties but am so disappointed to find they don’t come in wide.☹️ My feet need actual wide sizes.

    1. They do run wide but if you wear a WW or WWW they may not be wide enough.

  12. Oh Jennifer, as I totally agree with your sentiments about having comfortable shoes I too am looking forward to the revival of square toes and also appreciate that low kitten heels are on trend. That said; this past summer and as of late I have been footwear shopping and on the most part have been somewhat successful which I find surprising given the high to low end price range and that I wear a half size which is sometimes difficult to find. (ie.: For summer, got the cutest faux leather (removable) ankle strap sandals with a low wedge that were not only dirt cheap but sooooo comfortable that I purchased additional pairs in order to re-invent ( by solid or color-block dying, adding a different strap and/or removable embellishment). As for my Fall shoe wear, pricing has not been as forgiving but I am having fun in choosing all the colors and embossed patterns being offered. (Re their pricing here in Canada; unfortunately they are literally through the roof! Given an example for most of the shoes in the $200.00 range that you’ve featured; their cost on an average is $95.00 more (not including shipping if that be the case) so needless to say I do envy you … ☺. Loving your choices. -Brenda-
    P.S.: As am not sure about your policy re comments would appreciate confirmation if I could add a tip about ill fitting shoes that my daughter shared with me many years ago which other readers might find helpful. (She modeled internationally during her first few years of University.)

    1. Please share the tip with us Brenda! We’d all love to know.

      1. As brief as possible. While modeling in Tokyo (Runway & Editorial/Magazine) she often had to contend with ‘shoes’ either too small or too large and often had to improvise so used … DRUM ROLL ☺ …. pantie ‘incontinence liners’ or a portion thereof (adhesive strip/long length/thin ) instead of anti-slip/forefront insoles, a cushion foot-bed insert, heel grips or as a protector against and/or for blistered heels with no risk to damaging the shoe. Also similar to that of ‘no show shoe liner socks’; they work well for absorbing foot perspiration.
        So that’s the tip with hopes, it might be beneficial to some of your readers. -Brenda-

      2. What great tips!! Thanks for sharing Brenda.

  13. I love the crocodile texture on shoes and boots.
    The loafers you referred to from Everlane look beautiful and classic. I’m waiting for a pair of red loafers to arrive from Nordstrom’s. Can’t go wrong with their free shipping and returns! With aging feet, I am willing to spend a little more and purchase fewer shoes in order to get comfort and style.

    1. I’m the same way with footwear Jayne. I also hold onto my shoes and boots for a long time so quality, fit and a unique look is what I prefer. I adore, Nordstrom’s free shipping both ways. I usually order 2 sizes to compare and return what doesn’t fit.

  14. One thing I don’t need is another pair of shoes or booties but I would like to find a pair of croc booties. My problem is opposite to your’s, as I have narrow feet and most footwear is just too wide. And, I now put comfort ahead of fashion, well almost always. ? I like a 1” – 1 1/2” heel.
    I saw your instastory. You were beyond thrilled when picking up your grandson and being the first to share in this exciting event for him. Too cute!

    1. It was so much fun. It simply fills my heart to share his excitement.

  15. So glad kitten heels are back, so much more comfortable. I love booties and will be buying some this year for sure. Really liked all the shoes in your piece. You always wear great looking shoes!

  16. Great article on fall shoes. Can you also write an article on fall handbags? I need some inspiration in that area too!
    I enjoy your blog and I’m glad I found you.

    1. Thank you Carolyn. That’s a great idea for a posts. Stay tuned.

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