flatlay of women's dress shoes

The Best Dress Shoes for Women That Are Stylish and Supportive

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There is nothing more exciting than getting dolled up for special occasions — especially as the world starts to reopen again! Picking out show-stopping dresses and bold accessories is fun until you start to dread squeezing into tight pumps.

The truth is that women’s dress shoes have a bad reputation for causing foot pain and leaving behind blisters. However, the good news is that you don’t need to wear those terrible high heels or stiff loafers anymore. These days, there are a variety of shoe brands that offer comfortable and stylish dress shoes at reasonable prices. From sophisticated flats to modest heels, there are dress shoes that are versatile for work conferences, weddings, and dates.

But before you start splurging on new shoes, you must make the right choice, otherwise, you will end up regretting the purchase you made. Here are some factors to keep in mind if you want to find the best dress shoes for women.

  1. Choose the right size and perfect fit

If your shoe doesn’t fit, you will notice a gap between the shoe, your heel, and your arch areas. This can cause your foot to shift around while walking and will surely lead to foot pain and discomfort. When you are shopping for the best dress shoes for women, be sure to measure your feet for both length and width for a good fit.

Do you always have a hard time trying to find the best dress shoes for your wide feet? Rather than forcing your foot into slim shoes and pretending that the pain is worth it — you should check out comfortable shoes that are designed for wider feet. They usually have the roomiest insoles and flexible fabrics like soft leather to give your feet room to expand. Wide fit dress shoes with a rounded toe are also a great choice to keep you from getting sore toes.

2. Prioritize Comfort 

Don’t go for sky-high heels. The taller the heel height, the more pressure will be put on the ball of the foot. You should consider heels that are two inches or less to stop putting excess pressure on your foot.

Block heels are also more favorable than stiletto heels because they offer better weight distribution, stability, and long-term comfort. The other way of preventing sore feet is to opt for open-toe heels. This design will help relieve excess pressure on the front of your feet.

Still not sure what dress shoes to get? Below, we have rounded the 5 best dress shoes to shop today on Amazon. Each shoe style balances the perfect amount of comfort, style, and formality.

  1. Naturalizer Women’s Banks Pump

If you are looking for the best work shoes for your next board meeting, look no further than this strappy low heel option from Naturalizer. It has 800 reviews on Amazon and boasts a solid 4.5-star rating overall — and it makes total sense why people are obsessed with it. For one, it comes in wide fit sizes. Secondly, the outsole is slip-resistant meaning that you will not have to worry about falling over and injuring yourself at work. These office shoes are available in 9 different colors: classic black, silver to barely nude.

Just pair your pumps with skinny jeans and you will be ready to go from the office to happy hour in style.

What women are saying: “I usually hesitate to buy shoes online because I don’t get a chance to try them on. I know Naturalizer makes generally comfortable shoes, so I took a chance. The shoes fit my feet beautifully and are so comfortable to walk in. The icing on the cake is that they are truly lovely shoes that match almost all my outfits. A great buy for me!

2. DREAM PAIRS Open Toe Pump Heels Shoes

There is no need to suffer in uncomfortable dress shoes in the name of fashion. These comfortable heels will add sophistication and elegance to an outfit. Not only do these pretty sandals have a comfortable two-inch heel that you can walk in all day, but they have padded faux leather insoles for more added comfort. With over 2,000 ratings, these best-sellers from Dream Pairs are loved by Amazon reviewers, especially for how great they look and how comfortable they feel.

What women are saying: “This is not my first pair of dream pairs shoes… I will continue to purchase these shoes because I know the quality and comfort they offer. Perfect pump heel comfortable to wear and stylish. Will be ordering again in the future!

Related post: 7 Best Women’s Shoes for Foot Pain

3. Vionic Women’s Rosie Open Toe Heel

If you have flat feet, it’s especially important to get dress shoes that have good arch support. Slipping into the wrong pair of shoes can lead to heel pain like plantar fasciitis. So if you are one of the 20% – 30% of American’s with flat feet, Vionics has the best pairs of shoes for you!

These pretty dress sandals are the perfect addition to any sleek dress or pantsuit (I mean how cute is the pink strap?). A great thing about this block heel is that it has a built-in ortholite footbed to support your arch and deeper contours at the heel and forefoot,

What women are saying: “I love these sandals! The most comfortable ones I’ve ever owned. I have gotten so many compliments on them too. This may sound fake, but I’m trying to make all new shoe purchases by Vionic brand because I’ve had such a great experience with the three pairs I’ve bought. I haven’t dealt with plantar fasciitis since I started wearing vionics. Also good for people with thin ankles because the ankle strap isn’t sewn into the back of the shoe, so you can add more holes without putting the clasp in the front.

4. Anne Klein Wisher Fabric Wedge Pump

Versatile enough to be worn with dress pants or skinny jeans, these classic shoes are the best option for day wear and evening events. They have a not-too-high heel at only 1.5 inches, and they arrive in different materials, colors, and prints for every occasion.

What women are saying: “I wore these shoes for 18 hours the first day that I got them. I was on my feet most of the day and all evening. They were so comfortable – no pinching, no pressure points. The soles make the difference. They are soft and shock absorbing. The wedge adds nice height and good arch support. I thought the heel would look wide and chunky in the back, but it is just right. I got them in black fabric. They are now my go-to shoes. Classic style looks great with skinny jeans as well as dresses. I get so many compliments. They look like elegant fashion pumps but feel like athletic shoes.

5. Hush Puppies Women’s Chaste Ballet

There is a time and place for high heels — weddings, dates, and brunch. But when your job requires you to be on your feet all day — your feet will need comfortable flats. Give your precious feet (and soles) a rest by slipping in Huppies’ classic ballet flats! Amazon reviewers noted that they were comfortable enough to wear for long hours. Best of all, they feature a perforated arch, making them an amazing women’s work shoe.

What women are saying: “I now own these in two colors. One of my feet is size 9 and the other is 9.5. I ordered a 9.5 and both fit comfortably. I have extra wide feet but I find that with some brands even ordering the extra-wide size isn’t enough. These fit comfortably with no stretching. I love them!!! And bonus even though they are extra wide I don’t look like I have clown feet.

Just because dress shoes are notorious for being extremely painful, doesn’t mean that you have to swap them for boring, casual shoes. Luckily, in recent years, modern shoe brands have improved their offerings by marrying comfortable materials with fashionable patterns. And these 5 best dress shoes for women are proof that comfort and style are no longer mutually exclusive.

Now that you have the best dress shoes checked off your list, it’s time to search for shoes that will pair well with everything in your closet!

Up next: The Shoes That Go With Everything (Yes, Everything!)

Flatlay of women's dress shoes
Best dress shoes for women

Temwa Namandwa
Temwa is the fashion writer at My Chic Obsession where she covers everything from outfit ideas to the best styling tips . She lives for a good matte lipstick and LBD.