This post is brought to you by Zappos, and all of the examples we used were selected from the Zappos store.

I bat for Team Flats. One reason is comfort. My feet do not like to arch so flats or low heels are by far the most comfortable options. Another reason is practicality. I often dash around town all day at a fast pace braving the Seattle elements. All that said, I still like to wear heels because of their magical ability to elevate an outfit. I just have to be extremely careful when I select them. 

It’s amazing how many women share similar heel wearing challenges, most of which are rooted in some form of foot discomfort. Some find heels higher than one and a half inches agonizingly uncomfortable on the balls of their feet. Others get cramps in their arches. Some pinky toes are severely squashed no matter how wide the toe box, while bunions can cause immense all over foot pain. Well, between the needs of my own fussy feet and those of my clients, I could write a book on this topic. 

The good news is that there are great heel wearing solutions for Flats Fashionistas if you’re extra mindful about the design details of the shoe. I’ll run through those details so that you can prioritize according to the needs of your lovely feet. Since this is holiday season you may be thinking about buying a pair for someone else. In that case you might be able to use this as a guide.

Cushioning Comfort

It’s essential that all my heels have soft, spongy, cushioning insoles built into the foot bed of the shoe because that design feature relieves some of the pressure on the balls of your arched feet. For extra cushioning comfort, add a separate insole from your local drug store. The Sofft Ramona’s have been a life saver for ladies who have to wear heels all day. The Stuart Weitzman Forsures are even more comfortable because along with a cushioning footbed, there’s a soft width of elastic along the top of the shoe that stretches as you stride. It’s such a clever design detail! I suggested them to my client Karen who is wearing them with her leather dress, and she is thrilled with these pumps. 

Manageable Heel Height 

Heels don’t need to be super high. Unless I’m at a fancy function and can sit all evening, I like a one and a half to two inch heel because that height causes less pressure on the balls of my feet. I find that I can still walk fairly fast in a comfortable low heel, especially when it’s fairly chunky. Stuart Weitzman’s Puffystuff kitten heel is an example of a stable, dainty low heel, while Nine West’s Newkimmie is casual with a chunky low heel (Loafers are making a pretty strong statement next year just in case you were wondering about this particular style). 

Heels with Straps

Some of my clients complain that pumps fall off their feet. I usually suggest heels with some sort of strap to keep the ped in place. Mary Jane styles are a super solution, as are T-Straps like BC’s Big Country pumps. For something a little different, try a hybrid between a pump and an oxford, like Stuart Weitzman’s Midtime. Gorgeous shoe.

Boots Instead of Pumps

Heels can be made even more comfortable when you wear them with cozy socks. This is one of the reasons that I prefer to wear boots and booties than any other form of footwear. My Frye Taylors are wardrobe workhorses because of the manageable chunky low heel and brilliant fit. When I wear them with thicker socks, they are all day city walking shoes. But if you’re after a dressier and more classic ankle boot for the office, a simple sleek style like Stuart Weitzman’s Parttres are ideal. 

Oxfords and Shooties

These high vamped styles provide less coverage than ankle boots but more coverage than pumps. Heeled oxfords like Clarks’ Palmyra Erin and shooties like Fidji’s Alea E872 can be worn with skirts and dresses as well as jeans and trousers. I really enjoy these types of heels because they tend to look more playful than a classic pair of pumps, AND I can wear them with comfy socks and under jeans.

Wedged Heels

Some of my clients find that they can wear a higher heel height when the style is wedged. I have definitely found this to be the case and can wear up to two and half inch wedges, whereas I often battle to traipse around all day in a two and half inch chunky or narrow heel.  Gentle Souls Ridgual wedged booties are as cute as they are comfortable because there is lots of room in the toe box. Amalfi by Rangoni’s Dante style wedge is narrower and more streamlined, but has the added benefit of an elastic upper that moulds to the shape of your foot.


Platforms often allow you to wear a higher heel because they minimize the arch of the foot. For example, the Marlo from Kork-Ease has a high three and a quarter inch heel, but it’s one inch platform makes it feel more like a low two and quarter inch heel. La Canadienne Geralda’s two and half inch heel is platformed by five eighths of an inch, so it feels less than a two inch heel on the foot. The wedged style makes it even more comfortable.

Arch Support

Some of my clients also require arch support to prevent foot pain. Footwear brands like Taryn Rose and Dansko provide substantial arch support, but if that’s not sufficient, adding in your own supportive orthotic will probably do the trick. Size up half a size when inserting an orthortic. Taryn Rose’s Kelly is a particularly great choice because it’s wedged with an elasticated vamp, while Dansko’s Rhianna has a platformed advantage. For the longest time, I couldn’t understand why these footwear brands do not work for my feet. I eventually realized that my arches do not require that much support, and over supporting them is actually uncomfortable. 

While the specific examples I have used might not be to your taste, hopefully they illustrate the important design features that will help you find comfortable heeled footwear. In addition, remember that soft leather and a roomy toe box make a shoe more comfortable straight off the bat. And that some shoes can be stretched if they are snug in a particular area.

I’ve mentioned a few brands here that generally make comfortable and good looking heels, but there are plenty more. Brands like Chi Mihara, Anyi Lu, Fitzwell, Reiker, Paul Green, Miz Mooz, Cole Haan, Fly London, Tsubo, Fluevog, Aerosoles, Aquatalia, Naya, Born, Naturalizer, Dr. Marten, Pikolino and Donald Pliner are often worth trying because there is a good chance that they will keep your fussy feet happy. 

Please use the comment section to suggest other brands that make comfortable heeled footwear. Also mention what it is about their designs that makes those heels comfortable. This Flats Fashionista is always interested to hear more about comfortable heeled footwear options.