Comfortable Dress Shoes for Women

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Festive and Fashionable in Comfortable Holiday Shoes

It’s holiday time, so get the party going in some comfortable holiday shoes! Don’t have any? No worries; the Barking Dog has been busy gathering a sleigh full of beautiful, comfortable holiday shoe options for you. Won’t it be nice knowing your feet will look great AND feel good while you mix and mingle? Many online retailers have lightning-fast shipping options, so even if you’ve put off shopping your new shoes can be on your doorstep in time for next weekend’s party!   Here are our top picks for comfortable holiday shoes:

Comfortable Holiday Shoes

Earthies Lucca

Earthies Lucca (by Earth Brands Footwear):  Earth brand comfort in a graceful, beautiful shoe? Yes, please! These beauties will cradle your foot in comfort all day and through the evening thanks to versatile styling, a leather-covered high-density foam foot bed, anatomical arch support, and lightweight outsole. We also love the hook-and-loop closure – no buckles to fuss with! Available in sizes 5-12, in burgundy, navy and black. Click to view them at Zappos and Amazon.

Comfortable Holiday Shoes

Sacha London Vesta

Sacha London Vesta: We’re in love with this stylish shoe, and so are oodles of online reviewers! They rave about the Vesta’s high quality, fashion-forward styling, fantastic comfort, and lovely color options (including basic black and a gorgeous jade.)   Several reviewers say they’d given up on wearing heels until they found the Sacha London Vesta! Others talk up what a great value this shoe is because of its go-from-work-straight-to-a-party versatility. We’re fans of the 1” platform, which offsets the height of the 3” heel, the hook-and-loop ankle strap for a secure fit, and the cushioned foot bed. Find at Amazon.

comfortable holiday shoes

Rockport Kalila T-Strap

Rockport Total Motion Kalila T-Strap: Looking for a classic, graceful look in comfortable holiday shoes? The Rockport Total Motion Kalila T-Strap might be just right for you.   No one knows comfort like Rockport, so it’s no surprise this shoe boasts numerous comfort features to cushion your foot. It also has a polyurethane midsole plate for added support and stability. The 2” tapered heel is sculpted and sexy, but not too high.  And the lovely t-strap not only looks great, but will also help keep the shoes securely on your feet while you dance the night away. They’re available from Zappos and in sizes 5-11, medium and wide widths.

Comfortable Holiday Shoes

Naturalizer Okira

Naturalizer Okira: Hard-to-fit feet? No worries – you can still look festive and radiant in beautiful, comfortable holiday shoes! Naturalizer was one of the first shoe brands to offer women both feminine styling AND comfort, and they’re still at it with shoes like the beautiful Okira.   Many women will be thrilled to learn this shoe comes in sizes 4-12, and in THREE widths (narrow, medium and wide). The Okira also boasts Naturalizer’s N5 Contour technology – dual density cushioning on a patented contoured foot bed with arch support, so your feet should feel good all evening. Those of us in northern climates will appreciate the non-slip rubber outsole in case our holiday festivities are accompanied by slippery conditions underfoot. Available at Zappos and Amazon.

A video posted by FitFlop (@fitflop) on

FitFlop Classic Tassel Superoxford: Maybe you’ve read this far, and are thinking, “These shoes all look great, but I don’t EVER wear heels!”   Or you prefer trousers to dresses and aren’t into girly styles, but still want a fun, festive shoe. If either of these describes you, you might be as excited as we were to discover the Classic Tassel Superoxford from FitFlop. After creating their first sandal in 2007, FitFlop quickly became legendary as a comfort brand for even the most problem-prone feet. Thankfully the brand has expanded to include shoes like this fun twist on a classic oxford, all the while incorporating their trademark SupercomFF comfort features. The lightweight outsole means that even though the shoe is sturdy, it won’t feel heavy. And the lace-up styling is the ultimate in adjustability. Even reviewers with multiple foot issues give these shoe five stars for both comfort and style! Check them out yourself at Amazon,, Shoebuy. This style is selling out quickly, even at Zappos. For a similar style that’s currently in stock, see the Fitflop Tassel Superskate.

Rhinestone Shoe Clips

Rhinestone Shoe Clips

Festive Options for the Budget-Conscious: On a budget but still want to dress up for the holidays? You might already have a basic pair of shoes that can be fancied up with inexpensive shoe clips. You can find these bejeweled beauties and others at Amazon, ranging from $5 to $20. (Are you REALLY watching the budget? I’ve used clip-on earrings for the same purpose! Dig through your jewelry box and see what you might already have; just be aware that not all styles may work -and some might snag hosiery.)

Comfortable Holiday Shoes

Sofft Altessa II

If you don’t already have a shoe to wear with clips, consider a classic pump like the Sofft Altessa II.   This shoe is a budget-stretcher because it is a timeless, versatile style you’ll wear for years.  It also gets high marks for comfort thanks to a modest yet “high-enough” heel and cushioned foot bed.   Look for the Sofft Altessa II at Amazon, Zappos, or discounted (in certain sizes and colors) at

With all these options for comfortable holiday shoes, you should be set to have a holly jolly good time this holiday season! Do you have a favorite festive, comfy shoe we didn’t include?   Let us know in comments below!

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7 Responses to Festive and Fashionable in Comfortable Holiday Shoes

  1. Mary says:

    More Mary Janes ? Why is that the go to shoe for so many comfort brands? ?

    • Debbie Heida says:

      I can only share for me. As I’ve aged, I’ve developed bunions so I need a B width shoe but I still have my AA heel. Mary Janes are the only ones that work for me to accommodate the need for a wider footbed at the front but not fall off my heel when I walk.

  2. cedar says:

    I can attest to the beauty and comfort (most important for me) of the Rockport Kalia and the Naturalizer Okira. I have both in black suede, for holiday parties. My normal size is 8M; I had to buy the Rockport in 8W. (first wide ever) Although, like Mary above, I almost loathe mary jane style, but the Rockport is very feminine, delicate and sexy. I also love that the black is leather and suede and goes smashingly with my black velvet dress that has a satin lapel. I bought the Naturalizer Okira to wear with a black tiered sheath dress. The shoe is sexy, comfy, festive, and the highest heel I will ever wear.
    I did try the Sofft Altessa II, but did not find it comfy. Narrow in the toebox and not so well padded.
    I purchased a black suede (look like velvet) pair of Gabor 02.69 because the comfort and lovely factor was just way too high to not keep them. I will wear them with black velvet pants and a blue glittery tunic.
    Perhaps my greatest shoe find in recent memory: Soft Style Deanna in black/gold. Unbelievable price! Super comfortable and very chic. I’ll wear them with a black conservative dress.
    I did find Earthies to be a very comfortable brand, but didn’t keep the pair I ordered. I’m petite, and don’t like a strap to cut off my leg and make it look shorter.
    I love this holiday shoe post. Thank you.

  3. VAL says:

    So is the red/burgundy shoe in the picture at the top of this article the Vesta? I don’t see it online in this color, though.

  4. Sandy says:

    Are there any wide toe box dance shoes out there?

  5. Jaimie Dee says:

    Holy toledos shoe clips??? Mind blown. You must changed my life. O.O

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