Comfortable Work Shoes for Women (that are actually cute)

The following content may contain affiliate links. When you click and shop the links, we receive a commission.

When I was searching for cute work shoes online, the results brought up Asics as a top recommendation. That’s just not going to cut it. Finding the perfect pair of comfortable work shoes that are also stylish can feel like an impossible task, trust me. Many shoe recommendations prioritize comfort but forget aesthetics, leaving you with orthopedic-looking footwear that doesn’t match your polished work outfits (ahem, Asics). I decided to take on the task of rounding up my favorite work shoes as someone who has worked in corporate America AND someone who now works for herself from home, so if you’re looking for comfortable work shoes that are actually cute, this guide is for you.

Comfortable Work Shoes for Women (that are actually cute)

Loafers: Chic and Supportive

Loafers are the most fool-proof way to look polished while staying comfortable in a work setting. The right styles are supportive and add stability, and being able to slip them on and off is a huge perk. Since they’re flat, they’re a great option for anyone with back issues who might need to avoid pumps.

Sam Edelman Loafers

My first pick for work loafers is the Sam Edelman Loraine Bit Loafers. These come in a million colors and they’re made in whole and half sizes. You can wear them like a traditional loafer or fold the back down and wear them more like mules. While they’re very flat, I’ve never had issues with support or stability when wearing these – and I’ve had them for YEARS. They mold to your feet over time which makes them on of the very best workwear choices. See them styled casually on me here.

Madewell Corinne Loafer

Madewell’s Corinne Lugsole Loafer is another excellent option with a fun, trendy tread. The lugsole look is very popular these days, which makes these easy shoes to wear from work to dinner. Plus, they’re made with durable leather, so they last forever and are worth investing in. Since this is an older style, it can be difficult to find all sizes in stock, so be sure to check Amazon, Nordstrom, and ShopBop as well. See the Corinne loafer styled on me here.

Ballet Flats: Comfortable and Elegant

If you prefer a more feminine look for work, ballet flats are a great option. They’re lightweight and stylish, but they don’t sacrifice comfort. Look for a pair that has arch support, cushioning, and a well-structured sole.

Madewell Greta Flat

The Madewell Greta Flat is a refined version of the classic ballet flat with a more square toe. They’re made in either soft leather or suede and have a comfortable, flexible sole. I love the strap at the top that gives them that “mary jane” feel, too. These come in a few colors and materials, so you could opt for a brown or black to keep things super neutral or branch out into a fun green colorway for a fun pop. I got the raffia style last year – see them styled here.

Larroudé Blair Flats

I recently became obsessed with Larroudé shoes, and their Blair Flats are my top pick (I own in brown and navy). They’re VERY comfortable and have a cushioned insole that makes them easy to wear all day. These are a bit of an investment shoe, but with the amount of wear I’ve gotten out of them, I think they are more than worth it. They also make the Verona flat which is very similar, but with a fun buckle detail (I own these in green). See the Verona in this video here, and a photo in the Blair here.

Sneakers: Stylish Yet Work-Appropriate

Not Asics—don’t you worry! While athletic sneakers may not be suitable for the office, certain stylish sneaker brands make shoes polished enough for a casual work setting. I wouldn’t wear these to the office in a corporate setting, but if you can wear dressy jeans, for example, these sneakers should work well for your workplace.

VEJA Sneakers

VEJA makes leather sneakers that combine sustainability with sophistication. Their minimalist designs pair well with business casual outfits, and they’re truly comfortable on my feet all day long. I wear my VEJA sneakers with jeans, dresses, skirts, and shorts. You name it, and I’ve probably worn them with it. My favorite style from VEJA is the Recife Logo, but the velcro look might not be everyone’s cup of tea. The Esplar style has traditional laces and is a great option.

Here’s a photo where I’ve styled the Esplar.

Cariuma Sneakers

I discovered Cariuma sneakers somewhat recently, and now I’m wondering where they’ve been my whole life! I have a wide-toe box, and these sneakers feel comfortable all day. They also have a sleek, low-profile design that works especially well with dresses. I have the OCA Low style. I styled them with a dress in this photo.

Loewe Sneakers

If you’re looking for a luxury take on work-appropriate sneakers, Loewe Flow Runner Sneakers are the shoes for you. These sneakers are elevated and timeless, but comfortable and practical at the same time. They’re made of calfskin and nylon and have the prettiest rubber outsole that blends right into the look of the shoe. These will cost you a good bit, but they sure are cute.

Heels: Height Without the Pain

Heels can be notoriously uncomfortable, but certain styles offer a balance of height, support, and wearability. As someone with 13 years of corporate America under her belt, I can confidently recommend two different work heels that I loved for the office.

Sam Edelman Hazel Pump

The Sam Edelman Hazel Pointed Toe Pump is a staple for many women who want a comfortable heel. They have a padded footbed and classic, sleek design (along with the perfect heel height). I owned these for my 13 years working in Corporate America and just replaced them every few years (but a good cobbler can extend their life beautifully, so get them resoled if necessary!). I even wore them on my wedding day when I walked down the aisle on grass (before changing in Christian Louboutin heels for the rest of the evening!) I styled them for a work look here.

Marc Fisher Zala Block Heel

The second pair of work heels I recommend are the Zala Block Heels by Marc Fisher. These have a thicker block heel (hence the name), making them even more comfortable than the Hazel pumps. They come in various colors and have a feminine pointed toe that immediately elevates an outfit. I styled these Zala pumps here.

Sandals: Breathable and Office-Ready

For warmer months, sandals can be a great work shoe option—if they offer the right support and structure. And of course, they must be timeless and tasteful (be sure to get a pedicure if you’re showing your toes in the office). Look for sandals with cushioned insoles, supportive straps (flip-flop sandals tend to sound too casual when walking around the office with their “smack” on the ground), and non-slip soles to ensure all-day comfort while maintaining a professional appearance.

Margaux The Flat Sandal

I fell in love with Margaux shoes this past winter when I tried their Downtown Boot. The quality is amazing, the styles are timeless, and the boots were so comfortable that I’m convinced the rest of their shoes are, too. The Flat Sandal is a simple sandal option that would look great with casual work clothes. The ankle strap is trendy and flattering, but I appreciate that it buckles rather than ties since a wrap-up tie sandal would feel a bit too casual.

Dolce Vita Wink Sandals

I love the minimalist look of the Wink Sandals from Dolce Vita. They’re simple and classic, but the gold detailing elevates them just a notch. While they are slides, they aren’t the kind of flip-flop slides that will smack around all day, so they’d be more suitable for an office space. Want more straps? Try the Kesha style.

Key Considerations for Comfortable Work Shoes

When shopping for work shoes, keep these factors in mind:

• Arch Support: Helps prevent foot fatigue and pain throughout the day.
• Cushioning: Provides comfort and reduces impact on your feet.
• Material: Leather and suede mold to your feet over time, creating a more personalized fit.
• Stability: A solid sole with traction helps prevent slipping and provides balance.
• Versatility: A good work shoe should match various outfits and settings.

Finding the perfect work shoe doesn’t mean sacrificing style for comfort. With the right choices, you can have both! Whether you prefer loafers, ballet flats, sneakers, heels, or sandals, these options will keep your feet happy while complementing your professional wardrobe.

Shop The Post