Whether you go into the office every day, or you need shoes to wear with your conference outfits, you will want comfortable, stylish shoes, particularly if you are on your feet for large parts of the day. This article has lots of recommendations for the most comfortable work dress shoes for women.

What to think about when choosing your work dress shoes

While an uncomfortable pair of shoes isn’t so bad if you are sitting down for dinner, for example, if you’re at work all day, there’s nothing worse than shoes that pinch, rub or give you blisters. Think carefuly about what you need from a work shoe.

Flats or heels?

This will depend on your personal preference, how comfortable you find heels, and whether you are standing up or walking a lot during your working day.

Your office ‘dress code’

Depending on where you work, you might have a uniform, a dress code, or perhaps you have complete freedom so you can choose any stye you want when searching for the most comfortable dress shoes for work.

Most comfortable work dress shoes for women - Cathy wears pointed heels | 40plusstyle.com

Cathy @themiddlepageblog above (read her style interview here) chooses a pair of neutral shoes that would go with any of your work or weekend outfits.

Get her look with this exact shirt, blazer, jeans, pumps, bag and belt. Check out this similar necklace and sunglasses.

Do you need orthopedic support?

If you have foot problems, don’t forget about when when you choose your work shoes. Do you need shoes to support your arches, or do you have plantar fasciitis or bunions?

Materials

Natural materials such as leather are usually more forgiving and less likely to hurt your feet during your working day.

Most comfortable shoes for work - Nancy in knee-high boots | 40plusstyle.com

Nancy @nancysstyle above (read her style interview here) opts for classic knee high boots under her midi skirt.

Steal her look with this similar top, blazer, pleated skirt, high boots, belt and brooch.

Expressing your style personality

If you have freedom to wear what you want to at work, you can use your shoes not just to stay comfortable, but also to express your style personality. You could, for example, wear a bright pair of shoes with a neutral suit.

The most comfortable women’s dress shoes for work

Now that you’re thinking about what your work shoes need to look like and feel like, let’s move onto some specific, well-recommended shoes that you could wear for work.

Flats

Most comfortable dress shoes for women - Shan in flat black loafers | 40plustyle.com

First, some comfy, stylish, flat options for you. Shan @teachingonthegc above wears black shoes that would go with anything in your closet.

Check out this similar dress, blazer, tights (another option here), flats and scarf (another option here).

Nine west

A pair of neutral colored loafers will go with all of your day-to-day outfits. You could wear with a black suit, or perhaps with your jeans and a blazer. The metallic heel adds a point of difference to these Nine West pointed toe shoes.

Most comfortable work dress shoes - Nine West Lallin Pointed Toe Flat | 40plusstyle.com

Nine West Lallin Pointed Toe Flat
Website / Nordstrom

Nine West shops: website, Nordstrom, Amazon and Zappos

Tommy Hilfiger

A pair of loafers is always a classic choice for work. If you like a designer look, you could choose Gucci’s horsebit loafers. Or, for a very similar look, that is more purse-friendly you could opt for the Tommy Hilfiger’s loafers (below), which will give your work outfits a polished, professional look.

Most comfortable work dress shoes - Tommy Hilfiger Cozte Loafer | 40plusstyle.com

Tommy Hilfiger Cozte Loafer
Nordstrom / Amazon / Zappos

Tommy Hilfiger shops: website, Nordstrom, Amazon and Zappos

Vionic

Vionic is a great choice if you need arch support. If you want a funkier look for your work shoes, you could opt for the Vionic loafers (below) with their contrast sole.

Vionic Kensley Loafer | 40plusstyle.com

Vionic Kensley Loafer
Website / Nordstrom / Amazon / Zappos

Vionic shops: website, Nordstrom, Amazon and Zappos

The Office of Angela Scott

Take inspiration from menswear with the oxford style (below). The stripes and wooden soles are sure to get these shoes noticed.

The Office of Angela Scott Mr. Smith Stripe Oxford | 40plusstyle.com

The Office of Angela Scott Mr. Smith Stripe Oxford

The Office of Angela Scott shops: Nordstrom and Amazon

Tory Burch

If you love a classic style, Tory Burch is a great go-to brand. The ballet flats (below) come in a choice of six shades.

Tory Burch Georgia Ballet Flat | 40plusstyle.com

Tory Burch Georgia Ballet Flat
Website / Nordstrom / Amazon / Zappos

Tory Burch shops: website, Nordstrom, Amazon and Zappos

Franco Sarto

You could try a pair of tasseled loafers for a hip, preppy look. The Franco Sarto loafers (below) come in a choice of colors, and are well reviewed from women who say they always receive compliments when wearing them.

Franco Sarto Carolynn Loafer | 40plusstyle.com

Franco Sarto Carolynn Loafer
Website / Nordstrom / Amazon / Zappos

Franco Sarto shops: website, Nordstrom, Amazon and Zappos

Linea Paolo

Chanel is renowned for its toe-cap styles. But you could get a similar look from the LINEA Paolo pointed flats (below).

Linea Paolo Niche Pointed Toe Flat | 40plusstyle.com

LINEA Paolo Niche Pointed Toe Flat
Nordstrom / Amazon / Zappos

LINEA Paolo shops: Nordstrom, Amazon and Zappos

Massimo Dutti

Massimo Dutti is a good place to look for timeless classic looks so, it’s ideal for your work suits. You could add a pair of ballet flats to your look. The silver flats (below) will liven up your work style.

Massimo Dutti Leather Ballet Flats | 40plusstyle.com

Massimo Dutti Leather Ballet Flats

Massimo Dutti shop: website

Mona Flying

You saw some menswear inspiration with the Oxfords in this list. You could also try a pair of brogues. The Mona Flying brogues (below) are 100% leather and come in a vast choice of colors.

Mona Flying Leather Perforated Brogue | 40plusstyle.com

Mona Flying Leather Perforated Brogue

Mona Flying shop: Amazon

Heels

Most comfortable dress shoes for work - Yvonne in black pumps | 40plusstyle.com

Yvonne @funkyforty above (read her style interview here) chooses a timeless pair of black pumps to go with her check dress.

Recreate her outfit with this similar dress (other options here and here), pumps, handbag and sunglasses.

Naturalizer

The Naturalizer pumps (below) are completely timeless and will look good dressed up or down. They have comfort cushioning, making them a good choice to wear all day.

Naturalizer Everly Pump | 40plusstyle.com

Naturalizer Everly Pump
Website / Nordstrom / Amazon / Zappos

Naturalizer shops: website, Nordstrom, Amazon and Zappos

Vince Camuto

Block heels can be more comfortable to wear than stilettos as they distribute your weight more evenly. The Vince Camuto pumps (below) come in a choice of neutral shades.

Vince Camuto Hailenda Pointed Toe Pump | 40plusstyle.com

Vince Camuto Hailenda Pointed Toe Pump
Website / Nordstrom / Amazon / Zappos

Vince Camuto shops: website, Nordstrom, Amazon and Zappos

Margaux

If you prefer round-toed pumps, then take a look at the Margaux heels below, which have a slightly retro feel. Made in Spain, they come in a choice of nine colors, and they’re very comfortable to wear.

The Heel by Margaux | 40plusstyle.com

The Heel by Margaux

Margaux shop: website

Dune London

You could add a pop of color to your outfit with the Dune London slingbacks (below). They also come in black or beige if you prefer.

Dune London Cassie Block Heel Slingback Pump | 40plusstyle.com

Dune London Cassie Block Heel Slingback Pump

Dune London shop: Nordstrom

Söfft

For a slightly vintage look, you could opt for a pair of Mary Jane heels. These happen to be very on trend at the moment. The Söfft Mary Janes (below) are great for a special occasion or everyday.

Söfft Petra Mary Jane Pump | 40plusstyle.com

Söfft Petra Mary Jane Pump
Nordstrom / Amazon / Zappos

Söfft shops: website, Nordstrom, Amazon and Zappos

Jeffrey Campbell

If you like the look of loafers, but prefer a heel, you could choose the Jeffrey Campbell loafers (below).

Jeffrey Campbell Happy Hour Pointed Toe Pump | 40plusstyle.com

Jeffrey Campbell Happy Hour Pointed Toe Pump

Jeffrey Campbell shops: Nordstrom and Amazon

Cole Haan

Another heeled loafer option for you, the Cole Haan loafers (below) have a three-inch heel and a cushioned insole with support.

Cole Haan Chrystie Chain Block Heel Loafer | 40plusstyle.com

Cole Haan Chrystie Chain Block Heel Loafer
Website / Nordstrom / Zappos

Cole Haan shops: website, Nordstrom, Amazon and Zappos

clarks®

Unless you have a particular work uniform, you don’t have to wear shoes. You could, instead, choose a smart pair of ankle boots like the Clarks® zip booties (below).

Clarks® Violet 55 Zip Bootie | 40plusstyle.com

Clarks® Violet 55 Zip Bootie
Website / Nordstrom

Clarks® shops: website, Nordstrom, Amazon and Zappos

aerosoles

For a block heeled choice, you could opt for the Aerosoles boot (below) which have a sleek minimal style.

Aerosoles Cinnamon Mid Calf Boot | 40plusstye.com

Aerosoles Cinnamon Mid Calf Boot
Amazon / Zappos

Aerosoles shops: Nordstrom, Amazon and Zappos

Kenneth Cole

A pair of knee-high boots is another choice for your work wardrobe. Wear over slim black pants, or wear under a midi skirt or dress.

Kenneth Cole Justin Riding Boot | 40plusstyle.com

Kenneth Cole Justin Riding Boot

Kenneth Cole shops: website, Nordstrom, Amazon and Zappos

What are your favorite comfortable work dress shoes to wear? I’d love to hear your recommendations for the best women’s work shoes. Let us know in the comments below.

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The most comfortable work dress shoes for women | 40plusstyle.com

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Continue reading:

  1. Classy Business Outfits For Women Over 40 – Your Work Capsule Wardrobe Sorted
  2. The Most Comfortable Heels That Look Hip AND Are Comfortable To Wear
  3. How To Wear Jeans To Work And Still Look Professional
The most comfortable work dress shoes for women | 40plusstyle.com

Feature image by Yvonne @funkyforty

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