Regardless of today’s weather forecast, you and I know that fall has truly arrived. Any day now we will need to bundle up in a sweater, top our favorite tee with a sporty jacket or opt for long pants instead of shorts. So it’s smart to also make sure you have the shoes you need in your fall wardrobe. Let’s keep those feet happy and looking smart!

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Throughout today’s blog post I’m sharing some of my favorite footwear in my fall wardrobe. But I also have shopping widgets full of options in each category. And I’ve made an effort to collect an assortment of styles as well as a full range of price points. But remember, when it comes to shopping for shoes, comfort and wearability are just as important as fashion trends and good style.
Loafers
Loafers are such a good option for fall because they look smart and elevated, but, if you choose wisely, they can also be extremely comfortable. This year loafers are having a moment, in fact. That whole preppy vibe is wildly popular as is the equestrian theme. And the classic horse bit loafer, like mine shown below, is perhaps the best shoe to achieve those style goals.

My Talbots loafers shown above fit so nicely true to size. In fact, the fit is so good that I know I’ll be able to wear a thin sock with them, too. And yes, thin, sheer socks are slated to be very on trend this year. I’ll be wearing my loafers with these everyday sheer dot ankle socks that I recently purchased. They are spot on! (LOL, no pun intended!)

I love the quality and simplified style of my Ally loafers above. Use their size guide for the best fit. Ally features shoes in narrow, medium, wide and extra wide sizes, and the quality is bar-none. You can always use code KAYFLATS for 10% off your first pair of flats at Ally. For other Ally codes, as well as so many other coupon codes for savings for our Dressed for My Day community, check HERE or the PROMO CODES tab in the top menu.
I gathered more loafers that I feel I can heartily recommend below. Keep in mind that I’ve not tried all of these. But I am only recommending brands that I am familiar with and feel confident about their quality.
Sneakers
Because creating a little juxtaposition is such a cool thing, you’ll want some sharp looking fashion sneakers in your fall wardrobe, too. Wear them with jeans and track pants, of course, but have fun pairing them with trousers this fall, too. Remember, we’re talking about low profile sporty sneakers that will look chic with your streetwear here, not the running shoes you walk the neighborhood in.

I’ve worn my Vince sneakers so many times since I purchased them in the Nordstrom Anniversary Sale. They’re super comfortable and fit true to size. I love the brown details on them. And just today I purchased these Michael Kors two-tone suede trainer in chocolate combo. Ooh! And you can get 25% off on those!
Ballet Flats & Mary Janes
Don’t forget to have a pair or two of more feminine looking shoes in your fall wardrobe. Especially when you wear something menswear inspired, such as a blazer or pleated trousers, you may want to add a little femininity with a pointy toe flat, like the Ally flat I’ve shown below.

I haven’t always been a fan of ballet flats. I like the idea, but I always found that they rubbed me wrong on the heels. Until now.

I’m wearing these Una ballet flats in light tan nonstop lately. They have a cushioned heel, the leather is so luxe and soft on your feet, they’re beautiful, the elasticized straps are ample and not binding and, best of all, the suede on the interior of the heel prevents blistering. They’re comfortable right out of the box! The Una comes in a multitude of colors and textures and you can use code KAY15 for 15% off (I’m not sure for how long).
Pumps, Kitten Heels & Slingbacks
For even dressier occasions you’ll want a pretty pair of heels or two in your fall wardrobe. Slingbacks continue to be popular, and they’re definitely feminine and pretty. But this year we’re seeing the return of the classic pump as well.

I do like having a good pair of black pumps at the ready. But you may also want to have some in nude, cognac or brown, depending on your personal wardrobe of clothes for the season. And while the stiletto heel is making a comeback, you could also opt for block heel or kitten heel pumps if those fit your personal preferences better.

I’ve collected a good assortment of heels in the shopping widget below.
Booties
While I tend to wear my booties even more in the winter months, I know that buying them early is best. Booties sell out fast, so look now for the best buy in comfortable, fashionable booties that you can wear on the repeat to get the best cost-per-wear.

I wore these Ally lower block heel ankle boot in camel calf leather today and felt perfectly comfortable as I traipsed all over the mall. In fact, I’m sitting here at my desk in them right now. That says a lot when I don’t immediately remove a pair of shoes upon arriving home from a busy morning. Use the Ally size guide for the best fit. And I’ve located other great booties for you to consider in the shopping widget below.
By the way, someone may ask if Chelsea boots are still in style. Zip-up heeled, ankle boots will look more polished, of course. But I think the Chelsea boot has earned its place among the classics. It’s definitely still the best boot for a casual day, especially when the weather begins to get wetter and messier. I will certainly be wearing my Chelsea boots later this fall and into winter.
Bonus: Knee High Boots
I don’t tend to wear my knee high boots until it gets a little colder. But I included them in our list today because I’ve learned the hard way that these sell out early. If you want to enjoy wearing knee high boots with your skirts and dresses this fall and winter, hunt for yours now and snap them up.

Look for boots that feel fabulous and work best with your wardrobe. Yes, you can still wear knee high boots, especially riding boots, with jeans. I just don’t tend to do that. You’ll want to wear them with skinny jeans, of course, so that the leg of your jean fits nicely within the shaft of the boot. My Chocolate Brown Calf Leather lower block tall boots above are in their “Roomy” calf fit and they fit beautifully. They also come in camel, black and black suede.
I hope today’s blog post has been helpful as you consider the shoes you need in your fall wardrobe. Thanks so much for stopping in! If you enjoyed today’s post, you may also want to read How to Choose the Right Shoes for Your Fall Outfits. And you may enjoy the video below, too.
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Blessed for My Day
When I go into our kitchen in the early morning to turn on the coffee, I always use our dimmer switch to turn on the lights “just so.” Before I’ve had my coffee, I don’t want to be blinded by the light! For that matter, I like to ease into wakefulness. Know what I mean? So that dimmer helps me to adjust to the light a little at a time.
I’ve discovered that God’s Word is also a bright light, sometimes illuminating sins in my life that I hadn’t realized were there. If you’re not familiar with the Bible, reading it for the first time could feel a little like staring into a full beam flashlight. Ow! But if you’ll read a little every day, you’ll find that a daily dose of truth works like my kitchen dimmer switch. God will graciously, gently begin to show you the difference between truth and error. And He’ll also help you to navigate any changes you may need to make in order to align your life with His Word.
For everyone who does wicked things hates the light and does not come to the light, lest his works should be exposed. But whoever does what is true comes to the light, so that it may be clearly seen that his works have been carried out in God. ~ John 3:20-21
Love the classic pumps. Enjoy your vacation.
Fantastic information about shoes for fall and winter! Thank you! I believe I need to get busy shopping.
Hi, Kay. I always look forward to receiving the DFMD emails!!! I have a question-is ALLY only a made-to-order shoe? I am hesitant to order in case the fit is not good. I tried on numerous booties and loafers last week at Marmi and Nordstrom and came home empty-handed. Various toe or other foot situations so nothing felt comfortable enough to commit to a purchase. I still greatly appreciate you mentioning Sam Edelman as I can wear one of their loafers and kitten heels, which is a lifesaver for my wardrobe. TYVM for that. It really gave me a lift to finally have found shoes that are beautiful and comfortable and a perfect fit.
I am wondering if you are familiar with Vivaia. I see adds for it often.
I am disappointed that a black Blondo did not fit in either a 7 or 7.5. I was hoping to find a water-resistant shoe for fall and winter wet weather.
Last, I did not save your blog from a few months ago in which you mentioned two other fashion bloggers for women over 50. I love all of your videos but I am 5’2″ so sometimes if an item is not available in petite, it may not look proportionally best on me, even though I love the clothing on you!!!!! Maybe one of those friends of yours are closer to my height?
Thank you, too, for the wonderful devotions. God has given you a wonderful blessing in being able to express your faith so well. As a fellow Christian, I appreciate your encouragement.
Blessings, Lisa S
Hi Lisa, they do have sizes available already at Ally, but if they need to they make your size. And you can return both of those if they don’t fit, within 14 days of receiving them. Not only is the quality great, but they truly are extremely comfortable. My best advice is to use their size guide questionnaire and even call them if you have questions. They really want to help you get a good fit. And my experience is that once you find your size in their shoes, that is the size you will wear in all of their styles. Also, you can use all three of my coupon codes once, so KAYFLATS, KAYHEELS and KAYBOOTS.
I’m not sure which two petite friends I mentioned in a blog post, but I think I recall mentioning Poised Petite https://youtube.com/@poisedpetite?si=Nxy87v3hwuk9e-JC and Style with Serena https://youtube.com/@stylewithserena?si=e-bhy0ImwJ7ZGy94 both of which are shorter than me for sure. Hopefully that will be helpful. 😊
I Love shoes. I tend to have more than I need. 🙂Love your BFMD analogy. 🙂
I have nice choices in my closet for all the categories except the fashion sneaker. I am not sure I have the personality to pull them off with anything other than an athletic outfit. 🙂 Great BFMD!
Your devotion today hit me well. This is encouraging me to find a daily devotional for home use, something that’s been on my mind for months now. Thank you for these lovely Blessed for My Day scriptures.
Thank you to Lisa Springer for asking all the right questions about Ally. I, too, have been searching for the right fit on my hard to fit feet. Your answers are making it easier to take the next step and try their shoes.
Enjoy the beauty of Fall on your trip.
Tanya
Here’s a question completely out of left field & having nothing to do with shoes 🙂
Do you have a cashmere comb that you prefer? Looking online I’m overwhelmed at the choices. I’d rather just get a recommendation from you, my trusted blogger.
Thanksl
I actually just got in this Nori Trim and I’m really liking it. It’s multi-purpose, comes with replacement blades (which most do not), is rechargeable and wireless and comes with a carry case for travel. But if you’re just looking for a comb, I like this one.