Most Comfortable Shoes to Wear with Cocktail Dresses

When it comes to dressing for a cocktail party, finding the perfect shoes to go with your dress can be a bit daunting. The goal is to select a pair of shoes that will look stylish but also allow you to last the entire night without having to take your shoes off!

I’m sharing my top picks for the most comfortable shoes to wear with cocktail dresses and some tips for choosing the best shoes for your event.

Watch the Video of me Modeling this dress, here!

What shoes are appropriate for cocktail attire?

I often get asked about what shoes work best for different cocktail dresses, and it really comes down to your personal taste and preference. For cocktail attire, you want to choose shoes that are dressy but not too formal. Some options include pumps, slingbacks, and strappy sandals. Make sure you prioritize comfort when choosing your shoes, especially if you’ll be wearing them for a long event. Look for shoes with cushioned insoles and heels that are on the lower to mid-height side.

Watch the video of me modeling this Outfit, here!

While heels are a popular choice for cocktail attire, you can still look stylish and chic in dressy flats or wedges. Don’t let anyone tell you that you have to suffer in uncomfortable shoes to look good! The key is to choose shoes that are appropriate for the occasion and complement your dress.

Wedges are a great option if you want to add height, but prefer a more stable shoe. Just choose a wedge with a dressy design that complements your dress, and you’ll feel comfortable and stylish all night long.

Pointed-toe flats or strappy sandals with embellishments or metallic details are great options if you can’t or don’t want to wear a heel. These elegant black flats I’m wearing are from Paravano at Amazon and have tiny crystals that crisscross in the front, creating a very elegant look.

Watch the Video of me modeling this outfit, here!

Now, let’s talk about heels. They can range from a short kitten heel all the way up to sky-high stilettos. It’s important to choose a heel height that you feel comfortable with, taking into account your balance and the health of your feet. I personally have found myself leaning toward block heels recently since they easier to walk in, especially in grass or uneven paths.

However, I did purchase these black suede pumps with the crystal bow from the Drop at Amazon, and while they are aren’t marketed as comfort shoes, I found them easy to stand and walk in all night.

Tips for Choosing the Best Shoes for Your Event

Different cocktail events can call for different levels of formality. So, it’s a good idea to select shoes that match the overall vibe of the occasion you’ll be attending. I also like to consider the venue where the event will be taking place. For example, I wouldn’t choose stilettos for an event that will be taking place on a lawn.

Watch the video of me modeling this outfit, here!


The length of your cocktail dress can also have an impact on the type of shoes that will best complete your look. For instance, longer dresses tend to go well with higher heels, while shorter dresses can be paired with flats or kitten heels.

Where Should You Shop for Comfortable Dressy Shoes?

You can find comfortable formal shoes for women at various retailers. My favorite places to shop for dressier heels, wedges, and flats are department stores like Nordstrom, as well as online retailers like Amazon and Zappos. I always look for brands like Vionic, LifeStride, Naturalizer, Aerosoles, Skechers, and Easy Spirit, as they are known their comfortable footwear options.


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Most Comfortable Shoes to Wear with Cocktail Dresses

comfortable silver evening shoes
Slip-On Evening Shoe

1. Slip-On Evening Shoe

Bending over to fasten and unfasten a delicate ankle strap can be a difficult feat once you reach a certain age, and there’s no denying the ease that lies in a slip-on shoe! I love this one from LifeStride. Not only is it elegant and classic, but it’s constructed with their LifeSoft System® comfort package which provides all-day support, flex, and cushioning. Plus, a closed-toe design like this can be worn year-round!

comfortable black evening flat
Shimmer Ballet Flat

2. Shimmer Ballet Flat

If you’re looking to add a little sparkle to your look, consider a shoe with a little shimmer like these ballet flats from Skechers. With an Air Cooled Memory Foam® cushioning insole and a shock-absorbing midsole, these would be a great back-up pair of shoes to bring for a wedding reception or a lengthy event when you are ready to break-up with your heels for the night!

silver comfort evening shoe
Strappy Silver Heel

3. Strappy Silver Heel

If I had to choose one color of dressy shoes to have in my closet, I would probably choose a silver pair like these strappy silver heels from Naturalizer. This super versatile color looks fantastic styled with bold colors, busy patterns, or neutral shades like black or white. You could also pair them with a silver dress for a chic monochromatic look!

comfortable gold wedge cocktail shoe
Low Wedge Sandal

4. Low Wedge Sandal

Wedges are a great way to elongate your legs and add a little height without sacrificing stability. The low wedge design of these open toe sandals provides just the right amount of height, while the ankle strap ensures a secure fit. They come in 11 different colors and finishes including matte, suede, and metallics, making it easy to find the perfect pair to complement your dress.

comfortable red evening flat
Ankle Strap Flat Sandal

5. Ankle Strap Flat Sandal

If you’re shopping for a sandal to wear with a cocktail dress, you’ll want to look for embellishments like rhinestones or bows that elevate their level of formality. This glamorous  strappy sandal is available in a lot of great neutral colors, but this shade of red would be a fun addition to a black cocktail dress. Just add a red lip or clutch, and you’re ready to go!

comfortable silver cocktail mule
Silver Square Toe Kitten Heel

6. Silver Square Toe Kitten Heel

With their chic, open square toe and gracefully low heels, these kitten heels promise to keep your feet comfortable throughout any event. Metallic accessories like silver are trending this year, but you can also grab them in several other shades like pink, white, or beige with or without rhinestones.

comfortable gold cocktail slingback shoe
Classic Slingback Heel

7. Classic Slingback Heel

If you’ve researching comfortable women’s shoes, chances are that you’ve heard about Vionic. I’ve owned a few pairs of shoes and booties from this brand over the years, and I can confirm that they are ultra comfortable! Their classic slingback heel is going to be a versatile addition in your wardrobe that can go with you from weddings and funerals to work meetings and date nights. I’m also loving their slip-on block heel, which has a podiatrist-designed orthotic!

Shop More of the Most Comfortable Shoes to Wear with Cocktail Dresses

Shopping for a cocktail dress to go with your new shoes?

If you have an 2024 event approaching on your calendar and are in the market for a chic, stylish dress, check out What To Wear To A Wedding Reception Over 40.

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2 thoughts on “Most Comfortable Shoes to Wear with Cocktail Dresses

  1. Hello Deb,
    In your June 15 edition you had a section on wedding attire. I have a wedding to attend in January and I love the sheer long sleeve black top with either the sequin skirt or velvet pants. Where can I find them?

    Thank you!
    April Bruckmann

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