The Hunt: Comfortable Work Heels

2019 Update: We still love these comfortable work heels — but you may want to check out our most recent roundup of the best black heels for business attire instead.

Sure, we all know what wardrobe essentials for work professional women are supposed to have in their closets, but if you’re buying one for the first time or replacing one you’ve worn into the ground, it can be a pain to find exactly the right incarnation in stores. In “The Hunt,” we search the stores for a basic item that every woman should have.

Today we’re hunting classic, comfortable work heels — perfect for interviews, a starter work wardrobe, keeping at your office, and more. A few things to note at the get-go:

• of course you don’t have to wear heels to work — check out our recent roundup of cute flats for the office
• a note on comfort: comfort/walking with confidence is the top thing to look for — e.g., if you feel uncomfortable walking in 4″ heels don’t get 4″ heels! — you should feel comfortable standing in your heels for at least an hour (such as at a networking event) and feel comfortable walking at least three blocks (such as to go to a restaurant near the office with clients). You can change into your commuting shoes for longer treks or other more specialized situations, of course
• don’t forget you can wear black with navy
• take care of your shoes — scuffs, scraped leather, and more can be taken care of pretty quickly either by yourself or by a shoe professional — you can also replace heel tips and even the soles of your shoe with rubber portions to increase the comfort (here’s our post on how to make your shoes last longer if this is a big problem for you!)

Ladies, let’s hear from you — what are your most comfortable work heels? Are you Team Block Heel, Team Kitten Heel, or Team Stiletto? How long on average do your work heels last for you?

Before we get started, here are a few of the heels in our Hall of Fame category:

Pictured, row 1 (all under $100): one / two / three
Pictured, row 2 ($99-$600): four / five / six

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And here are a few specific categories of interest for those seeking comfortable work heels:

• Hall of Famers (specific styles that have stood the test of time): Michael Kors MK, Calvin Klein, Nine West, Rockport, Cole Haan (45mm and 75mm), Sam Edelman, Naturalizer, Comfort Plus by Predictions, Corso Como, Kate Spade New York, Mark Fisher LTD, Everlane, L.K. Bennett, Christian Louboutin, Ferragamo (blocky low heel), Manolo Blahnik, Prada
• Under $100: 1.State, Charles by Charles David, J.Crew Factory, Cole Haan (d’Orsay and low heel), Franco Sarto, Naturalizer, Nine West, Clarks
• 2″ or Under: Calvin Klein (trendy, classic, block heel), Everlane, Naturalizer, Vionic, Cole Haan (trendier option at DSW), Ferragamo, Trotters, Talbots, Boden,
• Splurges: L.K. Bennett, Jimmy Choo, Louboutin, Ferragamo,  Prada, Manolo Blahnik
• Extended widths (AA, C, W): Sam Edelman (NMW), Bella Vita (AA-EE), LifeStride (AA-E), Naturalizer (N-WW),  Rockport (B,C), Nine West (B, C), Ferragamo (2A, B, C), Comfort Plus by Predictions (B, C/D),
• Extended sizes (4-13):  Calvin Klein (4-12), Calvin Klein (4-12), Nine West (5-13), Comfort Plus by Predictions (5-13), Ferragamo (4.5-12), Prada (4-12)
• Comfort: Michael Kors MK Flex Pump ($99), Clarks, Rockport, Vionic, Bella Vita, Ferragamo, AGL (d’Orsay ankle strap), Manolo, Cole Haan (45mm), Rockport, Comfort Plus by Predictions, LifeStride, Naturalizer (don’t forget to check out our entire guide to comfortable heels!)

(Curious for our previous roundups of black pumps? In addition to the several specific shoes mentioned in our Guide to Comfortable Heels, here are our roundups from 2017, 2016, 2015, 2013 (interview pumps AND our low heel roundup), 2012 (under $250) and 2008.

And now to some featured pumps for today:

These $29 pumps from A New Day (basically the new Merona line) are best-sellers at Target. They also come in mint and lavender, and sizes 5-12 (medium and wide sizes). They aren’t marked as being Gemma heels, but I believe Target’s new “shades of nude” line of pointed toe pumps are also Gemma heels. Gemma Pointed Toe Pumps

I like the melding of the d’Orsay cut and the block heel — and all for $59. The shoe comes in five colors, sizes 5-12. Note that because the shoe is part of the Nordstrom Anniversary Sale, the price will go back up to $89 when the sale ends August 6. Sisteen Half d’Orsay Pump

Naturalizer has a bunch of shoes that have been around for a while (for example their platform pump and their crisscross strap pump), but I don’t remember seeing these sleeker pointy-toe heels. They’ve got 81 reviews at Zappos with a 4-star average, they use the N5Contour technology, and they come in a range of nude-for-you options. Huzzah. They’re $99, available in sizes 5-12 and four size ranges. Naturalizer Natalie

I don’t know if we’ve included Banana Republic’s “12-Hour” line in our previous Hunts, but they’ve been around for several years now and seem to be great sellers for them. “Wear them for 12 hours a day (or more) thanks to flexible leather, injected insoles for heel stability, comfort pods at the sole and skid-resistant outsoles.” AND, bestill my beating heart, “insole with added stability in the heel.” Nice. It’s a 3.3″ heel, available in sizes 5-12, and they come in many colors.  Madison 12-Hour

Readers have always been huge fans of Stuart Weitzman comfortable heels — and so for the best several years I’ve been bummed to see that their work heels were kind of waning as the brand seemed to focus on their Nudist sandal and the OTK must-have, the 5050. So it’s good to see that the Azalea pump pictured here is a bestseller at Bloomingdale’s — and it’s on a killer sale today, down to $199 plus another 20% (down from $398). (DSW and Zappos also both have the pump as well.)  Azalea Leather Pumps

I don’t usually like a bow pump — but this side bow from Prada really is lovely and, as Nordstrom notes, it “adds a jaunty touch.” Amazingly this is only a 3″ heel — it looks a lot taller to me. It’s $780 at Nordstrom. Note that Italist has versions with lower heels (some on sale!), as does Farfetch.  Logo Bow Pointy Toe Pump

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