Fashion and Comfort: Fabulous Dress Shoes

Whether you're working or going out with friends, comfortable dress shoes can make all the difference. Here are our top choices.
Comfortable dress shoes

I recently bought a pair of dress shoes for an evening out with my husband. I got the seal of approval from my fashionable daughter – they were chic and trendy, and I looked great in them. But there was a big problem: when I went downstairs to show them off with my new dress, I could barely make it back up the stairs. They were tight across the top, they rubbed my heels just the wrong way, and I could tell I was going to be down for the count before we even got to the restaurant.

I’d love to say I’m as tough as I used to be, and I stuck it out… that I put on my gorgeous shoes, put on a brave face, and put my best foot forward (pun intended). But that would be a lie. I dropped those puppies right back in the box and returned them the next day.

That’s what’s awesome about fashion. It doesn’t have to be a punishing and uncomfortable affair. When you find a pair of heels that kill your feet, you’ll find 10 others that are waiting to treat your feet like the little queens they are. While some designers are going simply for catwalk chic, most are aware that comfort matters. So before you settle for a night out with sore feet and aching heels for days to follow, allow yourself to go for the comfortably stylish option. Because they’re out there, just waiting to shine. 

Here are our top picks for comfortable – yet fashionable – dress shoes. 

Comfortable Dress Shoes for Mature Women

Disclosure: This post contains affiliate links.
Clarks Seren65 Strap Sandal, $47.99

Want to put your best, most stylish foot forward? Do it with a little help from the Seren 65 Strap sandal, an open-toe profile that dresses up denim in an instant. Underpinned by an impact-absorbing Cushion Luxe sock that keeps you feeling light on your feet, this leather silhouette channels contemporary flair with an on-trend squared toe and angular heel that boosts you – and your style credentials – to new heights.

Ecco Shape 35 Boot, $140

Elevate your everyday style with the ECCO SHAPE 35 boot, fashioned from a choice of smooth, full-grain ECCO Leathers and engineered with modern comfort technologies. While walking in a feminine boot with a thick heel, you can enjoy lightweight comfort and bounce, thanks to the ECCO Comfort Shank Technology and ECCO FLUIDFORM™ Direct Comfort Technology. An inside zipper allows for an easy on and off while the textile lining and removable insole add softness and breathability.

Naturalizer Harlene Boot, $83.99

This fabulous mid-shaft dress bootie is a luxury option for seasons to come. They feature contour+ technology for a premium fit and all-day comfort experience, as well as a non-slip outsole. 

Naturalizer Maxwell Ballet Flats, $89

This classic slip-on flat has an elegant design and all-day comfort. It includes responsive cushioning and is designed to fit the contours of a woman’s foot. 

Naturalizer 27 edit clive flats, $130

 Reach the peak of chic in this beautifully adorned loafer with a timeless feel. The smooth lining and insole offer natural comfort and breathability for unrivaled comfort. 

Rockport Farrah Slide Sandal, $90

Meet the Farrah: It goes with everything and is up for anything. With a lightweight design and stable block heel, these leather sandals have all-day comfort that moves from one destination to another with ease. 

Rockport Total Motion Esma Woven Heel, $99

The Esma pumps remind us of the era of American Camelot with their understated elegance. Pretty woven leather details accent the square toe for textural appeal, and low-block heels give just the right amount of lift. Total Motion’s exclusive flexibility and shock-absorption technology only add to the versatile appeal of these women’s shoes.

Dansko Lexie Shoes, $130

Lexie is a stylish mule with modern lines and a tailored look. Dansko Natural Arch technology will give you premium support to feel as good as you look in this essential addition to your work (and party) wardrobe.

Vionic Cynthia Loafers, $140

This reimagined classic has lightweight lugs, a statement accent, and superior support. The elasticized topline adds extra comfort so you can stay on the move well into the evening.

Vionic Brighton Ankle Boot, $150

Lightweight and perfectly versatile, this lug-soled bootie features water-resistant, soft-as-butter suede. Stretch gore at the ankle, a pull tab and a medial zipper make on/off easy. 

Cole Haan Vandam Slingback Pump, $150

Upgrade your wardrobe with the Vandam Sling Back Pump. The timeless silhouette has added comfort, so you can add style and charisma to any outfit without wanting to change your shoes after a long day. 

Cole Haan Grand Ambition Pump, $130

Cole Haan worked with the University of Massachusetts Amherst’s Biomechanics Laboratory to design a revolutionary collection that provides uncompromised fit, feel, flexibility, and cushioning. It’s called Grand Ambition. It will change the way you think about comfort.

Cole Haan Vandam Buckle Mule, $150

The Vandam Buckle Mule is sure to elevate any wardrobe. An elegant pointed toe and buckle detail add sophistication to this incredibly lightweight and versatile flat. Plus, it features 3D Lux Comfort, an innovative technology with three layers of foam in varying densities for shock absorption, arch support, and exceptional cushioning. 


We are giving away a $50 Amazon Gift Card every month to one of our subscribers! To enter, simply add your email address below. If you already subscribe, you will automatically be entered. Winners will be chosen randomly.

Related Posts: