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I distinctly remember when I was starting a new job in Corporate America about 10 years ago and searched for cute work shoes online… and 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 cute can feel like an impossible task, trust me. Many websites can recommend work shoes that are comfortable but forget aesthetics, serving up orthopedic-looking footwear.
So I decided to take on the task of rounding up comfortable work shoes that are not hideous. I worked in finance and corporate marketing for 15 years before leaving to run my own business for the last 12+ years, and my business is built around fashion. So you won’t find Asics in this round-up, though they’re still my top pick for cute athleisure outfits on the weekend.
Your Cheat Sheet to Comfortable Work Shoes
- Best loafer: Sam Edelman Loraine
- Best boat shoe: Sperry Slimboat
- Best ballet flat: Margaux The Demi
- Best affordable flat: Quince Italian Leather Ballet Flat
- Best Mary Jane: Madewell Greta and Larroudé Verona
- Best slingback: Sam Edelman (kitten heel and block heel)
- Best sneaker: VEJA Campo
- Best heel: Sam Edelman Hazel
- Best block heel: Sam Edelman Daniella
- Best sandal: Larroudé Milan
- Best bootie: Margaux Downtown Boot
- Best tall boot: Sam Edelman Sylvia
- Most comfortable overall: Sam Edelman Loraine Loafer
The Full Breakdown, Category by Category
If you want more detail than the quick-pick list gives you, keep reading. Below, I’m breaking down every category of work shoe I wear on repeat, from loafers to boots to sneakers, with the specific pairs I’ve owned and loved for years.
Loafers
Loafers are the most comfortable work shoes that still look put together, no matter your office dress code. The right pair is comfortable right out of the box and will last you for years. Plus, since they’re flat, they’re a great option for anyone with back issues who needs to avoid pumps.
Sam Edelman Loafers
My top pick for work loafers is the Sam Edelman Loraine Bit Loafers. These come in a million colors, and you can wear them with almost anything (if you need styling tips for loafers, check out this post). I’ve had at least two pairs of these in my closet for YEARS. They mold to your feet over time, which makes them even more comfortable with wear.
Honorable Mention: Madewell also makes great loafers, and their suede options are especially worth a look if you want something with a little more texture than the Loraine.
Scarosso Serena Cognac Mule
I recently got this pair of Scarosso Serena Cognac mules, and they’re absolutely stunning. They run true to size (I ordered my usual 37 in EU sizes; I’m typically a 6.5 or 7 in the US), and I appreciate that they’re a slip-on option for business casual Fridays. These are definitely an investment shoe, but if you’re climbing the corporate ladder, you know you’ll wear them for years.
Boat Shoes
Boat shoes have made their way back into my closet, and I’ve found they work just as well for the office as they do for weekends. The slim profile of the ones I own is less boxy than a classic boat shoe that has a rubber sole, which makes it easier to wear with fitted trousers or a straight-leg pant instead of just denim.
Sperry Slim Boat Shoe
I have worn my Sperry Slim Boat Shoe into the ground (I really should have sprayed them with suede protectant), and the leather has softened with wear, so they only get more comfortable over time. I usually pair mine with cropped jeans, but they’ll work with cropped trousers too if denim isn’t allowed at your office. If you want more styling options, I’ve rounded up boat shoe outfit ideas to match any dress code
Ballet Flats
If you prefer a more feminine look for work, ballet flats are a great option. They’re lightweight and a little dressier than a loafer or boat shoe, but they’re nearly as comfortable. I personally don’t find them as comfortable as loafers, but they’re definitely more elevated. That being said, ballet flats in general aren’t going to give you the support a loafer does, no matter the brand. My picks below are comfortable, but I’m not sure I’d walk all over downtown in them.
Margaux The Demi
The Margaux Demi is my investment pick in this category. It’s handwoven by a single artisan, and the leather is vegetable-dyed and hand-oiled before it’s woven, so it softens and molds to your foot the more you wear it.
Quince Italian Leather Handwoven Square Toe Flat
If you want the look without the investment price tag, Quince’s Handwoven Square Toe Flat in cognac is the affordable pick. It’s real Italian leather, and the handwoven detail is truly beautiful. I also like the unique toe shape.
Mary Janes
Mary Janes have made their way back into my closet as an on-trend, still-office-appropriate option that lands somewhere between a ballet flat and a loafer. The strap detail gives them a little more support than a traditional ballet flat, which I find more comfortable for all-day wear.
Madewell Greta Flat
The Madewell Greta Flat is my top pick in this category. It’s made in soft leather or suede, depending on the colorway, with a flexible sole that doesn’t need any breaking in. I’d keep it neutral in brown or black for the office, though it also comes in some fun, less corporate colors if you want to branch out. I’ve had these for 3+ years and still wear them multiple times a week.
Larroudé Verona
The Larroudé Verona is another favorite I’ve owned for years. It’s a woven macramé flat with a heart-shaped buckle at the ankle strap, and it’s genuinely one of the most comfortable flats I own thanks to the memory foam cushioning inside. It runs a little big, so I’d size down half a size from your usual. These are an investment shoe, but if you want the full breakdown of why I think they’re worth it, I wrote a full review of Larroudé shoes.
Heels
I used to think comfortable heels were a myth until I found a couple of pairs that get me through a full day of walking all over San Francisco for meetings in various buildings without (much) pain.
Sam Edelman Hazel
The Sam Edelman Hazel Pointed Toe Pump is my pick when I want a classic pump. The pointed toe is sharp but not overly pointed where you’re tip-toeing into witch category. The 3” height is manageable – it’s leg-lengthening, but not too wobbly. I have them in nude (and even wore them for some of my wedding day events), but they come in nearly every color you can imagine.
Sam Edelman Daniella
If a full pump is more than you want, the Sam Edelman Daniella Block Heel is my pick for something lower-commitment. The block heel gives it more stability than a thin heel would, making it a good option if you want a little height while prioritizing comfort.
Slingbacks
I didn’t expect to wear slingbacks again after years of pumps only, but I find them more comfortable than a traditional pump since you can adjust the strap of most pairs. So if you struggle with stepping out of heels or often need heel inserts to get the right fit, slingbacks will be your new work bestie.
Sam Edelman Farrah
The Sam Edelman Farrah is my kitten heel pick. The lower heel height makes it an easy shoe to wear all day (and it’s on trend), and the pointed toe is tres chic.
Sam Edelman Winfred
If you want a little more comfort, the Sam Edelman Winfred has a flared block heel instead, so it won’t wobble on you the way a thin heel can.
Sneakers
No Asics, don’t worry. While plain athletic sneakers don’t belong in most offices, certain sneaker brands make a version that’s dressy enough for a casual work setting. I wouldn’t wear these into a strict corporate office, but if your workplace allows dressy jeans, these should work just fine.
And you can certainly pair sneakers with dresses.
VEJA Campo
VEJA’s Campo sneaker is a clean, minimal leather sneaker that pairs well with pretty much anything in my closet: jeans, dresses, skirts, you name it. I wear mine with dresses just as often as I wear them with jeans, and if you want something with a little more personality, my favorite white sneakers roundup has a few other options in the same lane.
Sam Edelman Kallen
The Sam Edelman Kallen is a retro-inspired lace-up with a bit more texture and personality than the VEJA. It’s not quite as casual as my boat shoe picks, but it lands in the same office-to-weekend category.
Sandals
This is the category where I’ve made the most mistakes, so every sandal below made the cut for long work days, not just a few hours around the house or running errands.
Larroudé Milan
The Larroudé Milan is my top pick, and it’s my first choice when I want something dressier that still feels good by hour six. They’re truly gorgeous and surprisingly versatile, and the metal detailing makes them feel dressier than plain leather would. (For more options in this same neutral lane, I rounded up my favorite neutral sandals for summer here.)
Steve Madden Haydn
For an everyday slide, the Steve Madden Haydn is my pick since they’re simple enough to wear with jeans or a dress. If you want a similar look for less, I found a close dupe in A New Day’s Nina Sandal at Target, and I’ve got a whole roundup of affordable Amazon sandals if you want even more options in that price range.
Sezané Josepha
The Sezané Josepha Low Sandals in vintage black are my dressier pick for this category. They run a little big and wide, so I’d size down if you’re between sizes, and if you have a narrow foot, these won’t work well for you. (Read my full Sezane review for more sizing tips since the brand’s sizing is a little tricky.)
Booties
Booties are the shoe I pull back out every fall, and I’ve had the same two pairs for years since they carry me from cooler mornings all the way through the holidays.
Margaux Downtown Boot
The Margaux Downtown Boot in chocolate suede is my investment pick here (and I actually just got the black leather pair). The shape is the perfect amount of pointy and round, the heel is low without feeling frumpy, and they’re equally elegant with a dress as they are with jeans. They also work great with trousers and skirts.
Sam Edelman Saige
The Sam Edelman Saige Bootie is my pick if you want something more affordable. The pointed toe and block heel give it a sharper look than a standard ankle boot, and the zip closure makes it an easy on-and-off for busy mornings. I have it in black, and it’s become my default with everything from trousers to a dress and tights.
My Most Comfortable Work Shoes (When Comfort Comes First)
If I had to name the most comfortable work shoes I own, it’s the Sam Edelman Loraine loafers, no contest. I’ve had this style for years (in multiple colors and fabrics), and they’ve only gotten better with time. The leather molds to your foot the more you wear it, so by month two or three, it feels like the shoe was made for your exact foot shape, not just your size.
They’re flat, which means no arch strain from standing all day, and the bit detail keeps them from looking too plain with trousers or a dress. If your feet start to ache by early afternoon in most work shoes, this is the pair I’d point you to first.
Key Considerations for Comfortable Work Shoes
When shopping for work shoes, keep these factors in mind:
- Cushion & Arch Support – If you struggle with plantar fasciitis (a common issue if you wear heels a lot), you’ll want something with a molded footbed. (Although, to be honest, this can make shoes look a bit frumpy. You’ve been warned. I’d add an insert to my heels before going full orthotic shoe.)
- Material: Leather and suede mold to your feet over time, creating a more personalized fit, which is the benefit of investing in quality vs. a cheaper synthetic option
- Stability: This is particularly something to keep in mind with heels, as thinner heels will be more wobbly and less structured, even if it’s a lower heel height.
The Bottom Line
If you only take one thing from this list, start with the Sam Edelman Loraine loafers, then build out from there.
FAQs
What are the most comfortable work shoes for women?
My top pick for comfort is the Sam Edelman Loraine loafer, since the leather molds to your foot the longer you wear it. If you want something with a little more structure, the Sam Edelman Daniella block heel is my runner-up. Neither one needs a break-in period, so both are comfortable right out of the box.
Are loafers or flats more comfortable for work?
Loafers tend to offer more support since they’re built with a sturdier sole, which makes them a better pick if you’re standing or walking a lot during the day. And you can put inserts in them.
What are cute AND comfortable work shoes?
They’re shoes that don’t force you to choose between how they look and how they feel. Leather and suede pairs that mold to your foot over time, like loafers and Mary Janes, tend to hit that mark since they get more comfortable the more you wear them, without ever looking orthopedic.
What work shoes are best if you’re on your feet all day?
Loafers and sneakers are my go-to when I know I’ll be up and moving, since both have more structure underfoot than a flat or a sandal. If you need something dressier, a block-heel bootie like the Margaux Downtown Boot or a block-heel sandal like the Larroudé Milan gives you more stability for a long day than a thin heel or a pointed pump.
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