Comfortable Women’s Dress Shoes

Our recommendations in comfortable women’s dress shoes include mid and high-heel dress shoes and dressy flats.

All shoes are ideal for both business and after-work entertaining. All women’s dress shoes offer anatomical support, incredible inner comfort and outer style.

All shoes are available in various colors and sizes and can be purchased online with free shipping and the best prices through our partner sites, Zappos and ShoeBuy.

May your work days and nights be filled with comfort!

Free Shipping on all Comfortable Women’s Dress Shoes
comfortable women's dress shoes by cole haan
Cole Haan Air Talia

Classic style meets all day comfort in this lovely pump from Cole Haan. Leather upper. Leather lining. Concealed NIKE AIR technology offers ultimate cushioning. Mini platform, 2 inch heel. Leather sole. Various colors and wide and narrow widths available.
Comfortable Women's Dress Shoes by Ros Hommerson
Ros Hommerson Cabernet

These stylish 2 1/2 inch heels get rave comfort reviews. Classically styled upper is composed of the finest leather. Cushioned footbed with forefront and heel padding to reduce stress for all-day comfort. Durable rubber outsole provides secure, sure footing with each step. Available in various classic colors.
comfortable women's dress shoes by Dansko shoes
Dansko Bett

A gorgeous low-profile dress shoe from Dansko. Full-grain leather with adjustable buckle closure for easy on/off wear and a secure fit. Cushioned footbed with additional arch support and shock absorption for the ultimate in comfort. Also in Brown.
comfortable women's dress shoes by Naot
Naot Select

A premium leather comfort Mary Jane, elegantly tailored and graced with a soft leather footbed – perfect for work or with jeans! Also in Brown and Green.
comfortable women's dress shoes
Cole Haan Air Bacara Ballet Flat

Stylish and extremely comfortable slip ons. Made with premium leather. Padded leather sole gives all day comfort. NIKE AIR technology cushions the heel. Also in Patent, Silver Metallic and Berry.
comfortable women's dress shoes by Naot
Naot Trendy

The beautiful ‘Trendy’ Pump is a great shoe for professional women who value comfort. An exquisitely comfortable vintage leather career shoe with a patent leather upper and nubuck collar. Padded insoles cushion and support the foot for all day comfort. Cute color options available.
comfortable women's dress shoes by Clarks
Clarks Sugar Dust

An ultra-comfortable career shoe by Clarks. Superior arch support and padded footbed evenly distributes your body weight to prevent stress and offer all-day support. Ortholite footbed is removable allowing the use of personal orthotics. 2 inch heel. Also in Brown and Navy. Wide and Narrow sizing available.
comfortable women's dress shoes by aravon
Aravon Maya

A comfort dress shoe classic from Aravon. A rocker sole reduces pressure on the foot, ankle, toes and metatarsals and saves energy by eliminating thousands of small compensations the foot would otherwise make in each step. Also in Black.
women's dress shoes
Naot Pleasure

Functional yet feminine mary jane is the perfect comfort career shoe. Removable bow for a versatile look. Shock-absorbing, suede-covered footbed absorbs perspiration to keep your feet dry and fresh. 2 1/4″ heel. Also in Copper. Order a size smaller for best fit.
comfortable women's dress shoes by michael kors
Michael Kors Erin

A feminine comfort Ballet Flat available in a range of cute colors will complete any outfit. Soft leather lining molds to the natural shape of the foot. Padded footbed ensures proper support and absorbs shock for all day comfort. Elasticized topline provides a secure fit.
most comfortable women’s dress shoes, most comfortable women’s high heel shoes
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Cole Haan Women’s Shoes Offer Nike Air Technology

Cole Haan Heels, Sandra Bulluck wears comfortable high heels

Sandra Bulluck wears Cole Haan Air Pumps

Good-looking, comfortable high heels that actually coddle your feet? Yes, Believe it. Cole Haan and Nike have teamed up to design a new line of comfortable dress shoes that enlists the sportswear giant’s Air technology for maximum cushioning. Zoom Air bags inserted just beneath the lining—identical to the support systems in running shoes—counterbalance the pressure of standing and walking for hours on end, and won’t lose volume over time.

Though their prices tend to run upwards of $100,  their women’s shoes range from elegant pumps and sporty slip-ons to stylish leather flats with Nike Air cushioning. Unlike other shoemakers, who seem to let their focus on comfort overshadow any attempt at style, Cole Haan shoes are classy and chic while staying easy on the foot. These are a long-lasting, worthwhile investment.


To shop the full range of Cole Haan Comfort shoes CLICK HERE