Little things often add up to big results. It may surprise you to learn that something as seemingly insignificant as pairing the right shoes with your outfit can significantly impact how you look and feel when you step out the door. Today I’m teaming up with one of my favorite women’s footwear brands, Ally Shoes, to share tips for how to choose the right shoes for your fall outfits. You’re going to feel so in the know! {See the bottom of the blog post for an opportunity to win a $350 gift card towards Ally shoes! Ends 9/15/2025.}
How to Shop Here: To shop the items I feature, just click on the words in the captions of photos, the highlighted words in my text or the images in the shopping widgets I sometimes include. When you shop through my links I potentially earn a commission on your purchases, but at no additional cost to you. Thank you so much for supporting my work here by shopping my links. Items that have been gifted to me by the associated brand are indicated with “c/o”.
Choose Shoes that Are Stylish
Choosing the right shoes for your outfit is not as simple as just wearing your favorite shoes, your newest ones or the most on trend pair you have in your closet. And it’s not just about matching colors or wearing shoes that keep your pants from dragging on the ground. Your shoes are literally the ground level foundation for your outfit, and they can elevate your look or diminish your style. So take the time to choose a pair of stylish shoes to complete every look.
Choose Shoes that Are Comfortable
At the same time, we women over 50 know the importance of comfortable shoes that feel good on our feet and keep us healthy as we wear them. Many of us have even developed “issues” that require us to have substantial cushion, soft interiors, arch support and other engineered features in our footwear so that we can step out in confidence and without pain or discomfort.
That’s why I love my Ally Shoes, and I’ve been wearing them for over 5 years. I’ve worn Ally shoes for speaking engagements, conventions and other all-day-on-your-feet events. And I find them supportive and comfortable. They’re created by women for women, and they’re made to support women and their stride. I encourage you to visit their website and learn more about how they make their footwear so comfortable, but you’re also just going to love the look of these classic shoes and boots.
Choose Shoes that Fit Your Feet Well
Today I’m sharing with you just five pairs from my large collection of Ally Shoes. I’ve used their Fit Finder Quiz to find my ideal size at Ally, and every pair I’ve ordered using that guide has fit beautifully. For the best fit I suggest you do the same, and be sure to check at the bottom of this post for the coupon codes that can provide you substantial savings on your first orders of each type of Ally shoe.
c/o// beaded necklace // pendant necklace // earrings c/o
Choose Shoes That Set the Right Tone for Your Outfit
Every shoe you put on automatically sets the tone for your outfit. You, however, get to decide what the tone is when you choose those shoes. Will your shoe make your outfit look a little more elevated and polished, like my Bossy Beige Classic Pumps do here? Or will you give your outfit a more casual vibe with a sneaker or boat shoe? There’s a time and place for each, but choose wisely.
c/o
Side note: By the way, I made the mistake of taking the above photos after spending a day at the mall. My feet were swollen from being on them all day (in other shoes, not these!); otherwise my pumps would look a lot prettier on my feet.
Choose Shoes that Visually Elongate Your Legs…If You’d Like
Wearing a shoe in the same shade as your pant or skin can help elongate your leg visually. Your shoes don’t always have to accomplish this goal for you, but if you’re dressing up for a special occasion or want to look especially smart, this is a smart goal to attain. I often wear my Bossy Beige Classic Pumps to create a visually elongated leg.
When you’re wearing jeans, specifically full length wide leg jeans, it’s smart to wear a pointy toe shoe to maintain that long line visually. A rounded toe shoe can look stumpy and out of place with a wide leg jean. But a pointy toe boot like my Ally Leather Lower Block Ankle Boot in camel creates an uninterrupted visual line with my jeans. I’ll be sharing more in Wednesday’s YouTube video about which shoes to wear with different types of jeans this fall, so stay tuned.
Choose a Shoe that Balances Your Look Visually
Not only can your shoe help create a visual line, but it can also help create balance in your outfit aesthetically. For instance, in the outfit below I’m wearing deep cuff jeans. Those cuffs can look heavy and weigh the outfit down visually. They draw your focus down to my feet, which is not ideal.
But if you like wearing this trending jean, you can balance the look by wearing a pretty, feminine top with an open neckline and some nice jewelry, drawing the focus upwards. But your work isn’t done yet. If you wear heavy looking shoes – either dark or chunky or bright – you’ll bring the focus back down. So keep the focus up towards the face by wearing a shoe that “disappears” and doesn’t distract.
I’ve been using my suede and leather flats from Ally for over four years to accomplish that goal in similar outfits. I love the way they blend in with my skin so as not to draw too much attention. But if you do notice them, you’ll see that they combine two beautiful kinds of soft leather in one pleasing aesthetic. The low vamp is flattering and the ergonomically-designed insole along with the built-in metatarsal and arch support keep my feet comfortable all day.
c/o// beaded necklace // pendant necklace // earrings
Choose Shoes that Work with Your Other Accessories
It’s smart to remember that your shoes are really accessories to your outfit. Along with your belt and handbag, which are also often created in leather or suede, these are the icing on the cake.
But as any baker knows, icing doesn’t just sit on top of the cake making it pretty. Icing also holds the cake together. Likewise, your shoes, coupled with your handbag and belt, help pull your look together, making it appear cohesive and easy on the eyes. Choose your shoes, handbag and belt to create harmony with your clothing.
I’m a big believer in using rich leather tones such as camel, brown or cognac to bring interest, richness and depth to your outfit. That’s why it’s so smart – really necessary – to stock your closet with shoes, handbags and belts that harmonize. They don’t all three have to match, by the way. But I always advice women to try to at least almost match two of those key accessories, and then the third one can be different or the same, depending on what you have at your disposal.
c/o// beaded necklace // pendant necklace // earrings
Do you have questions about footwear that I didn’t answer? I’d be glad to answer your questions in the comment section. Just click on JOIN THE CONVERSATION below.
If you’d like to shop my Ally Shoes and a few other favorites that I’ve pulled from the website, I’ve collected them in a shopping widget below. Just click on the image to head to Ally. You can use code KAYFLATS for 10% off your first pair of Ally flats, code KAYHEELS for $40 off your first pair of Ally heels and code KAYBOOTS for $50 off your first pair of Ally boots. And yes, you get to use ALL THREE of those codes once for savings. Thanks so much to Ally for those generous codes.
ENTER for a chance to win a $350 gift card towards Ally Shoes HERE. Best wishes! The winner be will be chosen at random on 9/15/2025. See the terms of the drawing at the bottom of the registration form. Thanks to Ally for Sponsoring this drawing just for my followers.
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Blessed for My Day
When it comes to living well, we need more than good shoes to succeed. Oh, how we need the Lord to guide us and bless us each day! Sometimes we make the mistake of thinking that we can check enough boxes to feel good about ourselves. We’ll “measure up” if only we do one more thing or meet one more standard. But the truth is life is much more fragile and uncertain than that. We need wisdom and assistance from God to navigate this life successfully.
Today let’s ask the Lord to guide our paths. Let’s look to Him for direction and energy and sustenance along the way. When we prioritize doing His will and pleasing Him alone, we will find not only success, but also rest and great joy.
Teach me to do your will, for you are my God! Let your good Spirit lead me on level ground! ~ Psalm 143:10
Very helpful post! Your idea to wear neutral flats with wide-cuffed jeans is so good – dark or heavy shoes take away from the cuff feature. I wasn’t enjoying the wide cuffs til I saw your version today. Also, your choosing cognac accessories is great – shakes me out of always choosing black! Thank you for your special tips!
Kay, I so enjoy your writing style – you convey information with such clarity that I feel more informed rather than confused. Can you suggest how to wear a shoe like a leopard print flat or a red sneaker? I’m really looking forward to this week’s video as this is definitely a topic of interest.
Hi, I know you didn’t ask ME but I just wore my red sneakers the other day. I wore them with dark wash drawstring jeans and a white long sleeve cotton polo top with my red bag. I thought it looked good for a very comfy and casual day out for lunch and visiting sister in law in senior facility.
Love the boots. They are on my wish list.
Oh my goodness, this was so helpful! I half figured out on my own that round toe shoes do NOT look good – with trouser jeans. I gravitated toward my square toe, pointy toe, or loafers, because I could see they looked more flattering. So your point about how the rounded toe looks too stumpy, made sense. Thanks to you, I have one pair of Ally shoes. They are generally out of my price range, but at the time, I needed one key pair of shoes that I could not find anywhere else – a chocolate brown pump. So I bought a pair from Ally. They look great and are decently comfortable. I say decently, only because I have very blocky, squared-off toes, and pointy toe shoes have always been a slight challenge for me. But for the challenge I have, the Ally fit, well, decently comfortably! 🙂 I really appreciate understanding better ways to tie in footwear with my outfits. Love the handbag in the picture with the blazer, by the way, though you have no link (an older bag I presume). I’d scoop that bag up in a heartbeat! Looking forward to this week’s video.
Hi Carolyn. I’m so glad this was helpful and that you enjoy your Ally shoes “decently,” hahaha! I get it! I wasn’t sure which bag you were referring to. I think most of them are available, so I checked and realized that this bag was not linked and should have been. Is this the one you were interested in? It’s a great one! And it’s quite a good price for suede.
Yes, that bag! 🙂 Thank you, and I bookmarked the link.
They are beautiful shoes and complement all the clothing so well. I’m also looking forward to more ideas – I don’t want to be the complainer, but foot issues (which I hate and feel so unfair!) preclude anything like a pointy toe or a heel for me so I’m always looking for stylish shoes that will work for my problems, starting with needing a wide width and large toe box – I know the rounded toes aren’t necessarily attractive so I’m looking for a workaround! And yes, Thy will be done – even though we’re sure we know better what we want and need :)!
Would you be able to recommend under eye cream and/or something to help significantly with eye bags? I see the Origins eye brightener in the sale area but wonder what you’ve found to be the most helpful (what lasts, doesn’t crease, etc). Thanks!!
I don’t have that problem myself so o can’t speak from experience, but from what I read and hear, my best recommendation would be this Dr. Brandt Needles No More No More Baggage eye cream. They have other products they recommend to use with that one, too, and the results seem to be significant.
My feet swell in the heat and then my shoes become uncomfortable. Specifically when I wear heels that have a higher vamp which most dressy shoes do. I have been looking for dress shoes that I can wear on a cruise that won’t be uncomfortable with swollen feet from the heat. I am not willing to spend over $300 on shoes that will not be comfortable. I have tried other brands of block heels and slingbacks but none seem to be comfortable with swollen feet. What do you suggest?