‘This shopping guide for comfortable heels for work is inspired by one of our all-time top posts, The Quest for Comfortable Heels. We update the text of this page regularly and invite you to add your on-topic comments as well. Last updated: July 2024.
Forget the Holy Grail — the quest for comfortable heels can be a lifelong hunt for some women. In general, if you can find one pair of shoes you like, try other shoes from that brand (although there can be variances within that brand as well).
Note that for interviewing, you should be able to walk a few blocks in your heels comfortably; I would say the same for your first day on the job as well as any big meetings (since you may walk to lunch at a local restaurant).
Of course, flats are acceptable for interviewing and beyond, as well!
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Some Of Our Favorite Comfortable Heels
These are some of our favorite heels as of 2024, but check out our entire Guide to Comfortable Heels!
These are some of our favorite comfortable low heels for work as of 2024… also check out CK Calvin Klein, Trotters, Sam Edelman, and Sarah Flint!
Brands for Comfortable Heels
The most comfortable heel brands can be broken down into four price ranges, and then into two categories.
The first group holds the stylish/trendy brands that everyone swears by for comfort (whether or not they're marketed as “comfort shoes”).
The second group of shoes are marketed for comfort but often a bit funky/clunky when paired with, say, a pencil skirt.
For specific shoe recommendations other than those pictured below (both from Kat and the readers) check out our roundup of Top Ten Comfortable Heel Brands, as well as our regular Hunt feature (in which we hunt for one wardrobe basic or basic accessory in a range of prices) and our afternoon Coffee Break posts (which often feature shoes); you may also want to check out our post on upgrading your shoe collection.
The Most Comfortable Heels, Designer Edition
Hunting for investment heels? Some of the bestselling, highest-rated designer heels for work in 2024 include:
“Investment shoes” such as Christian Louboutin (but please know your office before considering thick platforms or 4″+ heels, see more things to consider below), Jimmy Choo, Manolo Blahnik, Aquazzura, Sarah Flint, and Miu Miu (one of the favorites in our Newbie Guide to Designer Shoes)
Special mention for comfortable (but pricey) professional flats: Chanel.
{related: here are our favorite investment ballet flats if you want something slightly fancy}
The Most Comfortable Mid-Range heels, $200-$500:
Stylish/trendy but reportedly comfortable heels:
The hands-down reader favorites are Stuart Weitzman and Salvatore Ferragamo — also try AGL (particularly for flats, but they make heels too), Cole Haan, Kate Spade (the brand's wedges were apparently a favorite in DC on political campaigns in years past), Paul Green, and SJP by Sarah Jessica Parker
Designed for comfort, but may be funky or clunky, depending on your taste:
Arche, Beautifeel, Earthies, Eileen Fisher, FLY London, Gentle Souls (by Kenneth Cole), John Fluevog, Pikolinos, Taryn Rose, Think!
Special mention for comfortable flats in this range: AGL, French Sole, Paul Mayer, Salvatore Ferragamo
Affordable Comfortable Heels (under $200):
Stylish/trendy but reportedly comfortable heels:
Donald J Pliner, Franco Sarto, Geox, Isolá, Sam Edelman, Sofft
Designed for comfort, but may be funky or clunky, depending on your taste:
Aravon, Børn, Camper, Clarks (particularly the Indigo or Artisan lines), Cobb Hill (by Rockport), Dansko, Ecco, Josef Seibel, Miz Mooz, Munro, Ros Hommerson, Tsubo, Umberto Raffini shoes at The Walking Company
Special mention for comfortable flats in this range: Børn, BP
Budget-friendly Comfortable Heels (often under $100)
Anne Klein (particularly the iFlex line), Bella Vita, Comfort Plus by Predictions (at Payless, now also at Amazon), Corso Como, Soft Style (by Hush Puppies), Sole Society, and Trotters. Read our other tips on great shoe bargains, below.
Other Notes on Comfortable Heels:
Particularly great for high-heeled winter boots*: Aquatalia by Marvin K., Frye, La Canadienne (most are waterproof! See our roundup of weatherproof shoes for work here.)
Mall stores that bring trendier shoes to you at a more reasonable price: Naturalizer (particularly their N5 lines) and Rockport
Brands that you can still find on eBay and other resale sites: Anyi Lu, Cole Haan Air (from Cole Haan's late, great collaboration with Nike), Hollywould, Sacco, Sudini
Comfortable flats: We've mentioned a few brands or styles for comfortable flats in each price range, above — do check out our previous discussions on comfortable flats and flats for job interviews, as well as our best tips on how to look professional if you ONLY wear flats. (It can be done!)
Some of our favorite comfortable flats for work as of 2024 include M.M.LaFleur, AGL, and French Sole. On the more affordable side, check out Rothy's, Sam Edelman, and Rockport. We've also rounded up the best loafers for work, and our favorite sneakers for work outfits!
In our last poll on comfortable heels, readers mentioned other favorites including Alfani Step n' Flex, Brooks Brothers, Butter, Calvin Klein, Coach, Enzo Angiolini, J.Crew, Joan & David Circa, Seychelles, VANELi, and Via Spiga.
We've also named names for some of our least comfortable heels (brands and styles). If you're looking to upgrade your shoe collection in general, you may want to check out our discussion on the different tiers and levels that people consider for shoes.
Special Sizes: Wide heels can be found; we've also talked about general shopping tips for problem feet. In our more recent Hunts, we also try to include picks for wide/narrow widths, extended sizes, and (for boot round-ups) wide and narrow calves.
Some of our favorite comfortable wide heels as of 2024 include (below): 1) Sam Edelman 2) Naturalizer 3) Walking Cradles 4) A New Day (under $30!) 5) LifeStride (also, N.B.: the styles at Inez, Margot, Ally Shoes, and Poppy Barley all look great and come in wide widths!…) You can also try this link for a Zappos search narrowed to just the best brands and wide widths.
Comfortable Heels in Narrow Widths & Small Sizes
In our last roundup of classic black heels for business attire, we rounded up some pumps that came in extended widths, including:
- Extended widths (AA, C, W): Target (M/W), Vionic (MW), Rockport (NMW), Ferragamo (2A, B, C), Trotters (M,W, WW), Sam Edelman (NMW), Bella Vita (AA-EE), LifeStride (AA-E), Naturalizer (N-WW),
- Extended sizes (4-13): Target (5-12), Calvin Klein (4-13), Ferragamo (4-11),
Avoiding Pain in Heels
Alleviating Pain Caused by Shoes, During:
Inserts can make a big difference with heels! I've liked Dr. Scholl's and Foot Petals.
Note that some shoe maintenance (such as asking a cobbler to put rubber soles and rubber heel tips on your new shoes) can increase comfort as well as extend the life of your heels.
I've also been a longtime fan of ball-of-the-feet inserts, like those by Dr. Scholl's or Foot Petals.
Finally, if you really can't walk far in your heels, there are a number of foldable ballet slippers that you can stash in your purse:
Alleviating Pain Caused by Shoes, After:
YogaToes can also be miracle workers after a long day in heels or on your feet. The book Your Feet Don't Have to Hurt has a bunch of great foot exercises that help flex the muscles that might be sore after walking in heels.
We rounded up some of those exercises in our post for how to make your sore feet feel better, such as drawing the alphabet with a pointed toe, or spending a few minutes, barefoot, trying to pick up a pencil with your toes. I would heartily recommend the book if only for that section!
Commuting in Heels?
Although some rockstars can walk for miles in their five-inch heels, don't worry too much if you can't.
While some women who walk to work prefer to wear wedge heels, my personal secret has always been to have a pair of commuting heels like Clarks or Danskos that are nearly the same height as my office pumps, and then switch into the prettier ones at work.
(Check out our guide to hem lengths for thoughts on which lengths look best with what kind of shoes.)
Finally: Shoes are so much more comfortable (and last longer, and look better) when they're properly taken care of — don't skimp on shoe care to make your shoes last longer, and take steps to keep your shoes odor-free.
Where to Find Great Deals on Comfortable Heels
If you know the exact name of the brand or the style name you're looking for, Amazon is hard to beat — they often have sale shoes in lucky sizes for steep discounts.
Beyond that, Nordstrom shoe sales are great (particularly with their generous return policy!). You can also occasionally find good deals at discount stores like DSW or Nordstorm Rack.
{related: check out my other internet shopping tips!}
For pricier shoes, resale sites like eBay or The Real Real can be a great way to get lightly used merchandise at a good price (but proceed carefully).
* Know your office before buying! Remember that peep-toe shoes are not appropriate for every office; the same goes for shoes with heels higher than 3.5,” over-the-knee boots, and even knee-high boots (yes, really).
Readers, which brands are your favorite for comfort? Do you have any tips and tricks for making high heels more comfortable?
Liked this article? Don't forget to check out other Corporette shopping guides.
2020 updated images via Deposit Photos / IgorVetushko (woman in pants suit, trying on d'Orsay heels while sitting in beige chair). Earlier social media images via Shutterstock / Martin Novak (woman with pink sneakers changing into black heels) or Deposit Photos / studio-fi (woman trying on black heels while sitting on black leather tufted bench).
Emily
I have a really hard time wearing heels all day due to a common condition called sesamoiditis. As a result, I often wear heels when needed but keep flats close by for commuting. However, I can wear any pair of Nine West’s 3′ heels without consequence all day. I’m not sure what it is about the fit, but I’ve never had any problem with them. One of my co-workers also swears by Nine West heels.
2L NYC
Nine West heels are the best, I agree. Also, they last forever. Apparently they change the shape of the toe region every year on some of their classic heels, but keep the rest of the shoe the same — I know because I tried to buy an identical shoe to one I bought in 2006.
j
A majority of people on this blog seem to hate Nine West, but I can wear the Nuncio for hours on end, and I’ve had the same 3 pairs for 4 or more years.
Anonymous
I have a closet full of Prada, Stuart Weitzman, and other expensive shoes, but my Nine West Nuncios are my favorite. I own four pairs. The finish is perhaps not as spectacular as on the Prada’s or Weitzman’s, but if you ruin a heel in a storm grate, you don’t burst into tears. The Nuncios make my legs look fabulous, and I can wear them all day with no issues.
Pam Szoke
So glad to know this about nine west, where do I find them, I wear Ecco’s getting a little to expensive.
sunshine wang
Seriously, fit is everything. I recently started buying from a brand that does shoes made to order on your exact feet measurement. The brand’s called True Gault. The heels are so comfortable and gorgeous at the same time! I have since left all my designer shoes in the closet :/
Alex Park
If you have sesamoiditis you need a very good arch supported shoe, I would suggest Salvatore Ferragamo Vara, it has unparalleled arch support. Heels height is only at 1 1/4″ inch its one of the most comfortable heel to get for office wear.
http://www.onlybestshoes.com/salvatore-ferragamo-vara/
alhambra
Cole Haan Nike Air, hands-down, especially if you get the lower-heel version (I have the Air Mid Talia). Also, I don’t find my Louboutins to be particularly comfortable. They’re well-made, but a 4″ heel (100mm in Loub-speak) is a 4″ heel, and there isn’t much you can do about that.
I bought my husband a pair of Cole Haan Nike Air loafers and now he can’t stop talking about them, which is another bonus: if you can convince your husband to spend the extra money on comfy shoes, he might be more forgiving about your shoe budget.
Alessandra
Cole Haan Nike Air – Air Miranda — These will forever and always be my most favorite shoes. At $200 they aren’t the kind of shoes you buy every6 months but you won’t need to. They last forever and if you build a good rapore with your Cole Haan store, they will polish them for free and give all kinds of free comfy inserts. Not to mention, Cole Haan shoes go on sale all the time. I’m constantly finding great deals. Best shoes, hand down. I wear heels everyday to work because I’m short and work with all men. I need to have a little more authority.
Virve Georgeson
Alhambra, it is no wonder you don’t find Louboutin’s comfortable. They are infamous for being difficult to wear. Christian Louboutin has said it does not matter to him if women are in pain when they wear his shoes, he has been quoted as saying: “High heels are pleasure with pain. If you can’t walk in them, don’t wear them.”
High heels are usually uncomfortable for two reasons, one is the sheer height of the heel for your foot length, and the other is a flaw in design that looks good but is not compatible with the function of walking. Shoe design should adhere to the Bauhaus principle “form follows function”
The same height heel (for example a four inch heel), will feel very different on different size feet.
If a shoe has a four inch heel – and you have a short foot, such as size 6, your shoe’s ramp will be at about a 22 degrees angle to the ground and your ankle will be in much more pain than a woman with a size 9 shoe where the same four inch heel will only give her an 18 degree ramp angle to the ground. It’s a matter of the geometry of the triangle. The long side of the triangle which is the ramp, is in relation to the other two sides which are the heel height and the distance from the heel to the middle of the ball of the foot.
Sculpted shoe inserts that hold the foot back from sliding down the ramp inside the shoe will help to stop pain in the toes, in the ball of the foot and keep the heel in position, but they can’t do anything for ankle pain due to the extreme bend of the foot downward if the shoe ramp is really steep. You are right ” a 4″ heel (100mm in Loub-speak) is a 4″ heel, and there isn’t much you can do about that.”
The most comfortable way to wear quite high heels such as four inches, is to wear platforms. A four inch heel is then ‘cut down to size’ to be a mid heel of three inches.
anon
I have shoes from Audley, Gentle Souls, Hispanitas, Chie Mihara, Faryl Robin, Butter and Cydwoq (their shoes are pretty funky) that I consider quite comfortable.
Miss Outlier
I have found Clarks to always make excellent comfortable shoes in my student price range. And the bonus is, for the last couple seasons the styles have been getting less and less clunky, so I heartily second that option.
I don’t see Miz Mooz on here, and those I have always found comfortable. Not usually in stores, though, have to get them online, and the styles tend to fall in the funky Fluevog category.
Serena
For cheaper shoes, I love Tahari – so comfortable and you can get them at DSW.
Cole Haan Air are hit or miss for me. I’ve bought 2 pairs that were seriously uncomfortable.
EM
I agree–I find that the Air part reduces toe room and makes them squished and blister prone.
Kristen at Batterlicker.com
Cole Haan Nike Air usually work for me, but I recently bought a pair of heels by Butter on sale and, despite the 3″ heel on this particular pair, they are truly comfortable! I typically bring a pair of flats to switch into for any walking further than 3 blocks – at first, I did this for comfort, but now that I have found some more comfortable heels, I do it to save the heels from the uneven streets in San Francisco.
Angeline
I’ve had the best luck with Calvin Klein and Enzo Angiolini for classic heels (which I can usually find for under $100). For fun colors or details, I like Nina’s lower-heeled options (up to 2.5″)…a little on the fancy/dressy side, but they add some nice pizzazz to a regular biz cas outfit. And of course any heel is more comfortable with a Dr. Scholl’s For High Heels insert thrown in (helloooo gel arch support).
Laura
Cole Haan Nike Air – anything for me – the mid talia ones are my go to shoes for giving 4 hour lectures to graduate students.
Anonymous
manolo, stuart weitzman, enzo (in order of cost and style)
wrkbrk
YEAH Franco Sarto!
Virve Georgeson
I agree with YEAH Franco Sarto! I have a pair of sling back platform wedges and even with a medium high heel they feel very comfortable to walk in. Part of their appeal for me is that the bottoms are very light weight so they stay on the foot very well. When I put my contoured foam high heel inserts into them they wear like flats for either all day at the office or for a kilometer walk to the corner store. The wedge high heel sling back style with peep toes looks great with both dresses and pants, or jeans. Love them!
Bunkster
The most comfortable shoes I own (note I say “shoes”, not heels) are from this brand:
http://shop.nordstrom.com/sr?keyword=athena+alexander&origin=PredictiveSearch
Unfortunately, they only appear to make sandals/open toe shoes. I have the “Benny” pair from this season, as well as a pair from an earlier season. They have extra padding in the footbed.
In summer, I wear these shoes to work every day. They’re awesome. I just wish they made shoes for all seasons.
TX Attny
Bunkster, I love the pairs of Athena Alexander sandals I have! Spent about 5 hours walking the San Antonio Riverwalk in a higher-heeled sandal, and my feet never flinched.
Selia
I really like Kate Spade pumps – great colors and styles – and very comfortable. For what it is worth, I have a large (10) wide-ish foot.
NYC
FYI, Taryn Rose no longer owns the shoe company by her name, but the company still makes comfortable shoes. DSW sometimes has a few styles in stock. Taryn Rose (the person) has a new budget line sold on the Home Shopping Network (High Heel Power) and is reported to be starting a high end line with Neimans (Haute Footure). No idea if they are comfortable, but I would guess yes, given her background.
My favorite work pumps are from Botticelli. I would put them in the “designed for comfort and mid-range pricey” category. They make some very sensible but fashionable work shoes and are on the less expensive side for shoes actually made in Italy (their boots are still a fortune, though). Seinfield fans might also recognize the brand from the episode where Elaine buys a pair…btw, the website is a little busted, so this might be a nyc-only recommendation…
UnSub
I like the Cole Haan with the Nike Air, but right now I am absolutely loving Kenneth Cole New York with the 925 Technology. I bought two pair for $40 each (75% off!!) in their Las Vegas store last year and they are fabu. I feel like I am walking in tennis shoes and they are stylish and well-made. I have to stop myself from wearing them everyday. Highly recommended.
SV Associate
Without a doubt, Cole Haan Nike Air. I have a wide range of shoes in my collection – 3-inch pumps, 4-inch pumps, boots, work-appropriate sandals, and casual sandals. I can’t complain about any of them.
Amanda Kay
I have bought no less than 3 pairs of the Nine West Barbe pump. They’re affordable, comfortable, and come in a variety of colors and finishes. I adore them.
Michelle
I’ve bought no fewer than 5 pairs of Calvin Klein pumps – very comfortable, and classic.
Ballerina girl
I find Calvin Klein shoes to run a bit narrow–just a PSA for those out there who run into this problem.
D
I second Calvin Klein Diema for a 1.5 in heel or Dolly for I think a 3 in heel.
I agree they do run narrow but they’re great for narrow footed people like me since they don’t slide out as easily!
Break in period is almost nil,which i a huge bonus. I’ve worn them around the mall right after purchasing and they’re almost done breaking in already. I can feel the little bumps my toes made in there. :)
jc
I have been hunting for comfortable heels for a lifetime (it seems). My hands down favorite are a pair of Facconable peeptoe sling backs that are 3 inch high. They are so comfortable despite the height. I have tried every brand named above in varying heights and none are as comfortable as the Facconable. My feet are on the wide side (but not enough to warrant “wide” shoes) and I have a narrow heel. I used to think that it was the narrowness of the shoe that was making them uncomfortable, but after trying on pairs and pairs of shoes, it is not the width, but the depth. I think I need a deep toe box or the space between the bottom of the shoe and the vamp. I guess I have thick feet (sounds awful, no?). I have had some luck with the Calvin Klein pumps of late, but need the heel stickies to avoid shoe slippage. If anyone has any other recs for thick footed people, please let me know!
Michelle
Corso Como – extremely comfortable!!
Debbie
I second the Corso Como recommendation — priced right, extremely comfortable without being stodgy and fashionable enough to wear to after work events too!
Jennifer Tipping
Thank you for the Corso Como rec, I’m desperate for comfy heels for an upcoming trade show x 4 8-hour days on my feet. Can’t wait to try. Brining my Rothy’s flats as a backup!
constructlawgirl
Kenneth Cole Reaction, the 9 to 5 line are the best! I’m wearing a black pair right now and the cushioning is luxe on my feet despite the 4″ heel! Highly recommended at around $200/pair.
annie
after purchasing my first pair of cole haan nike pumps last spring, i will never again buy another heel; they are so incredibly comfy yet classic. i would recommend them to everyone.
mamabear
I second the Cole Haan Air. I find they run somewhat narrow, but the cushioning is great.
Alison
A few friends of mine recommended the Alfani Step ‘n Flex line from Macy’s. I was skeptical, but they (Gracie and Denny pumps) were so comfortable from the first minute I tried them on. I have yet to put them through the test of walking marble floors at my new workplace or go through an entire day with them, but they come well recommended from many other friends.
Best part, they’re one of Macy’s “everyday values” at $59.98.
mamabear
As I mentioned in the other thread, I have found Farylrobin heels quite comfortable. They don’t have a ton of cushioning, but they are well made and the heels are usually sturdy. They are of a style – rather than classic stilettos – with a chunkier heel most often, but I could walk blocks in them. A bonus is that the wider heels won’t get stuck in sidewalk cracks and the like.
anonymous
Naturalizer.
Sadie
I couldn’t agree more. My go-to black heels are Naturalizer, and I have a couple of cute pairs. They’re all VERY comfortable.
Olivia
I’m a Naturalizer fan, too. They are quite comfortable and very reasonably priced, especially if you wait for sales and promos. Though, I can’t wear even their heels anymore (nothing over one inch) due to arthritis in one of my feet.
SS
I’m a Naturalizer fan, too, but missed the one’s made in the 80’s/90’s that were lined in nylon tricot, and had the stretchiest leather, and felt so soft to wear all day long!
stpetegirl
Can anyone rec comfortable heels for high arches? I’ve found some luck with the Nurture brand from Dillards along with some Foot Petals Arches inside, but I am wondering if anyone makes heels with arch support. (Also important would be a price tag under $300, with extra points for being under $150!)
a lawyer
Cole Haan Nike Air for the most part have good arch support. I stick with 2-2.5 inch heels.
Anonymous
I have the world’s highest arches. I find arch supports are only helpful in flatter shoes. In heels, I just need to find a pair that fits well and provides all-over support. A very strong and stable shank is particularly important when you have high arches. Generally, Stuart Weitzman seems to be the best overall line for my high-arched foot, but the brand is at the edge of your price range. The 9-West Nuncios are super comfortable, very attractive, and less than $75.00, sometimes much less. Finally, when you can afford Prada someday, they are fab. (Very expensive shoes have very strong shanks; try on a pair of Jimmy Choos or Manolo’s and you’ll see what I mean.)
foot surgery girl
Sofft work great because they have extra padding under the ancle.
Also, try these inserts which have a “gel – bubble” under the arch and make my extremely high arches and weak ancles feel great with many shoes that would not be supportive enough otherwise: http://www.drscholls.com/drscholls/productSearch.do?method=doProductDetailsLookup&searchArg=51
kgoods
Ann Taylor pumps.
Kady
Second – Love the perfect pumps. Have owned 4 pairs of them, bought over several years. Comfortable and durable.
BC from SoCal
I have been in search of the perfect pair of pumps forever. I want to buy something not made in China, that has a 2-3 inches heel, no chunky heel or super skinny heel, no toe cleavage, somewhat wider shoes than a size medium, but wide. Is my list too long? I must have weird feet.
al
I’m also a Corso Como fan. See here: http://corsocomoshoes.com/shop. I believe they’re made in Brazil. They don’t always have an appropriate pump every season, but I check back often. When available in other brands I usually opt for wide sizes, but medium width works for me in these shoes.
jcb
I like corso comos, but the last pair of flats I bought were way too tight across the ball of the foot. I don’t wear wide sizes, either. Maybe it was just an off pair.
Chie Miharas are always comfortable, but I can’t speak to whether they have wide sizes. I think they’re spanish? They are a little funky, not for everyone, but the heel is never skinny or chunky.
BC from SoCal
Oh, I forgot to state, these pumps must be comfortable and do not make too much noise while walking on tile floors.
Ann Marie
No one has mentioned Fitzwell; is that not a common comfort brand? I bought a pair of 2.5″ Fitzwell Player pumps a while back. The brand has a range of styles, from pointy heel/stiletto to chunky/clunky, but the prices are great. My pumps are extremely comfortable and very classic, bordering on boring, which is great for upcoming interviews. I’d like to get more pairs of pumps from them (higher heel/pointier toe), but it would be nice to get confirmation that others find them comfortable at the 3″+ heights.
Anita
Seychelles have not been mentioned yet. They are the most comfortable heels I own (and I own a lot ;p).
They are well-padded, stylish, have rubber soles so I don’t slip on polished floors and the prices are very reasonable.
Rachel
I second Seychelles – comfy and often cute.
srs
I third this. In fact, I’m wearing a pair of Seychelles right now!
Jami
I stumbled upon the Nurture brand at a Dillard’s about a year ago. I loved the padding in the shoes so much that I walked away with 4 pairs. They are cute, and so comfy! I have even run in my heels! There’s so much padding in the sole that it’s able to adjust to the shape of your foot. They are also reasonably priced. These are my go-to shoes for when I need a basic, every-day shoe. I highly recommend these!
Keri
I have been really happy with a couple of pairs of Corso Como shoes. They have a really nice leather padded footbed with a lot more padding than most shoes.
Eek!
You by Crocs are amazing!
The look absolutely nothing like Crocs, but carry the Crocs comfort. They tend to run about $100 for heels and about $200 for knee-high heeled boots. I’m happy to have found them and readily recommend them.
Theresa
I am always in search of a perfect pump. My best pair right now is a pair of Me Too wedges – I swear I could walk in these all day. http://shop.nordstrom.com/s/me-too-lightning-wedge/3144174
I just wish I’d bought them in red while they were still available. The patent pewter is cute but too close to black. They do give a little toe cleavage but they are so cute and comfortable I don’t care. They are also the first pair of pumps I have been able to comfortably wear both with and without stockings.
Meg
Ecco. The style can often lean toward the clunky, but occasionally you can spot a good work shoe. I bought a pair of Ecco pumps after recovering from a pretty severe ankle break – for a long time they were the only non-flat shoe I could wear. Not only comfy all day long, but even after wearing them almost daily that year, they still look great!
SadWriter
Second the Ecco shout-out. I heart the Ecco Junction. Incredibly comfortable and sleek, and not at all chunky-heeled.
Coaster
This is such a great list. Stewart Weitzman and Cole Haan are my general go-to brands, but I’ve also bought some pretty nice shoes from Ara, David Tate, and Easy Spirit (they do actually make a few stylish pumps).
Anon.
ROCKPORT PILOT PUMPS. Enough said. They are AMAZING and at least half the price of Cole Haans.
Ashe
Only have the one pair, but I’ve found Paul Green to be exceedingly well-made. Comfortable for their height and style, and I’m super picky.
Nan
If price is no object, I recommend Thierry Rabotin ($400 +). Beautifeel are wonderful, but a bit pricey ($200+). Munro American makes very comfy shoes you can buy for less than $200, but they are generally best with pants. There are so many more comfort shoe brands today than there ever used to be. It’s wonderful!