The Hunt: Strappy Pumps for Work
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Sure, we all know what basics 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.
I've said it before, I'll say it again: I find classic pumps challenging in tights (damn my narrow heels!). As the weather gets colder, though — particularly if you're commuting in rain boots or snow boots — tights become more practical.
My way of dealing with this has always been to keep strappy pumps at the office. They've become some of my favorite shoes over the years because I find them much easier to walk in.
We haven't talked about strappy pumps in almost a while, though, so let's discuss…
Readers, what shoes do you wear with tights in the winter? Are you a fan of strappy pumps for this purpose — or do you prefer to wear booties and shooties? Bought any great ones recently?
Our Latest Favorite Strappy Pumps for Work
As of 2025, these are our latest favorite strappy heels for work — also check the brands J.Crew, Valentino, and Jennifer Chamandi for strappy pumps. If you’re looking for strappy commuting shoes with heels to maintain a hem length, we recommend Dansko, Eileen Fisher, or FLY London.
Our Latest Favorite T-Strap Pumps for Work
As of 2025, these are some of our favorite T-strap pumps for work — Nordstrom also often has a bunch!
Our Latest Favorite Mary Jane Pumps for Work
Mary Jane pumps are on the comeback in 2025 — Manolo Blahnik has had this heeled Mary Jane for years, and Nordstrom and Jennifer Chamandi both have a lot of options, as does Valentino. In terms of affordable options that are less than $350, Rothy's has a version, and Amazon also has these affordable Nine West pumps. (Also, take a look at the trend of Mary Jane flats…)
Our Latest Favorite Ankle-Strap Pumps for the Office
Ankle-strap pumps can be slightly hard to find in 2025… one of our longtime favorites is this affordable option from Anne Klein, and Nordstrom has a surprisingly large selection of ankle-strap heels right now, including this nice pair from Naturalizer. If you prefer flats, Dream Pairs has a bunch of options (such as this or this), and Eileen Fisher usually does as well.
Great Strappy Flats for Work
Stylish strappy flats can be hard to find! As of 2025, these are some of our favorites — also, in general, check J.Crew, Boden, Jennifer Chamandi, Manolo Blahnik, and Valentino (on the pricier side, obviously). Nordstrom also has a surprisingly large selection!
The Best Mary Jane Flats for Work
Our general favorite Mary Jane flats for work in 2025 include Dolce Vita, Sam Edelman, and Manolo Blahnik. We also like comfort-first styles from Rothy's, Vionic, and Dansko. Looking to splurge? Manolo Blahnik just started making their classic Mary Jane heel as a flat, as well.
Some Specific Strappy Pumps for Work We Love
Naturalizer
These T-strap pumps from Naturalizer are a great bet for strappy pumps for work — and even better because T-strap pumps are hard to find. You can find the shoes at Nordstrom (where they also have an ankle strap style from the brand, also).
Easy Spirit
I primarily think of East Spirit as a comfort brand, but they do have cute shoes from time to time — such as this strappy heel! Not only are they affordable, but you benefit from the comfort — there’s arch support and a cushioned insole.
The heels come in 9 mostly neutral colors, but as of this writing there are the red patent heels as well as silver and tortoiseshell options.
The shoes come in sizes 5-12, in regular and wide sizes (in some colors), for $49-$99. Note that this Calvin Klein pump is very similar if you're hunting for an option in a different color or size.
Anne Klein
Another longstanding favorite strappy pump is this ankle-strap pump from Anne Klein... over the years it's come in a bunch of colors and materials, including party shoe options, as well as some pale beige options, and it's almost always under $75.
You can find the Anne Klein heels at Zappos, Amazon, and others… a close dupe that's a bit more affordable are these Dream Pairs ankle strap pumps that are highly rated on Amazon.
Calvin Klein
These Calvin Klein pumps with an asymmetrical strap look great — the way the strap crosses the vamp of the foot is really flattering, and I like how the outside of the shoe has a d’Orsay look.
The shoe comes in 9 colors at Zappos (including two beiges and a brown, if you’re hunting for nude-for-you heels). They come in sizes 5-11, and are $99.
Jennifer Chamandi
These green lizard-effect heels from from Jennifer Chamandi are stunning. It seems so simple but I honestly can’t remember a strap clasp being on the top of foot instead of on the side — I like how it almost takes the place of a minimal bow or other decoration.
The brand has a lot of strappy heels in neutral colors, but these green ones jumped out at me. Gorgeous, gorgeous.
They’re available in Italian sizes 36-41 at NET-A-PORTER for $840.
Vionic
These low, affordable, comfortable heels from work only have a baby Mary Jane strap — but they could be just what you're looking for if you need a higher vamp. These shoes have been a reader favorite for years and years but are getting harder to find — right now Amazon has the biggest selection of colors and sizes, starting at $27. (Also keep an eye out for them on resale sites like eBay!)
Valentino
Valentino's Rockstud shoes have been around for years, and they're definitely distinctive, with a bit of a “tough girl” vibe. If that appeals to you, go for it — they're one of the most reliably stylish T-strap pumps with a closed toe. You can find them at any upscale department store (Nordstrom, Neiman Marcus, Saks) as well as on resale sites like eBay and Etsy.
Manolo Blahnik
I think Manolo Blahnik's classic Mary Jane has been around since the earliest days of this blog — and it remains one of the most sophisticated iterations I've seen of the Mary Jane. It comes out in different colors and textures — keep an eye out at spots like Bergdorf Goodman, Nordstrom, and Net-a-Porter. (You can also sometimes find it at resale shops like eBay and Etsy!)
Like this feature? Check out other recent installments!
More of Our Latest Favorite Work Heels
The Best Office Heels In General
Hunting for comfortable work heels? We've got a whole guide just for that, but as of 2025 some of our favorites include Marc Fisher LTD, Sam Edelman, M.M.LaFleur, and Cole Haan. On the pricier side, check out Ferragamo, Stuart Weitzman, and Sarah Flint. For comfort-first styles, look to Vionic, Sofft, and Naturalizer.
Our Latest Favorite Low Heels for Work
Some of our favorite comfortable low heels for work as of 2025 include Sarah Flint, M.M.LaFleur, Ferragamo, CK Calvin Klein, Trotters, and Sam Edelman!
Where to Find the Best Nude-For-You Heels
Some of our latest favorite nude heels for every skin tone in 2025 include the following — see the full post for all the details!
Our Latest Favorite Investment Heels
Hunting for investment heels? Some of the bestselling, highest-rated designer heels for work in 2024 include Ferragamo, Stuart Weitzman, Sarah Flint, Jimmy Choo, Manolo Blahnik, and Prada.
Where to Find the Best Budget Heels for Work
Stay tuned for a roundup of the best affordable heels for the office! In general as of 2025, good brands to know include Anne Klein, Bella Vita, Comfort Plus by Predictions (still around even though Payless has closed), LifeStride, Sam Edelman, and Trotters.
The Best Comfort Dress Heels for Problem Feet
If you're seeking “comfort heels,” check out brands like Clarks, Naturalizer, Trotters, Cole Haan, Sofft, Vionic, and Lifestride! If you definitely want a stable base, check out funkier brands like FLY London, Dansko, Eileen Fisher, and Børn — they're great as commuting heels (because you can maintain height for pants hemmed for heels), but they may also be just the ticket if you want something more comfortable.
Some of our latest favorite comfort heels for 2025 are below…
The Best Wedge Heels for Work
As of 2025 there are a lot of wedge heels for work lately that look great for commuting or learning to walk in heels… Other brands to look for wedge heels include J.Crew, Vionic, Vivaia, Nine West, and Bandolino.
Our Latest Favorite Heeled Ankle Boots for Work
As of 2025, some of our favorite general boots for work outfits include the ones below…
Our Latest Favorite Heeled Knee-High Boots for Work
As of 2025, knee-high boots with a heel are back! Some of the best-looking options include these from J.Crew, Schutz, Veronica Beard, Staud, and Stuart Weitzman. If you're looking for an affordable alternative to try the style, check out these boots at Loft, or these boots at Amazon, both under $100.
I need someone to remind me that company’s that are hiring operate on their own schedules. Short take: Final interview on Friday, told I could hear as early as Friday afternoon or Monday (today). I know even being told that, that’s a highly compressed timeline and I need to sit on my hands and distract myself for at least a week. But it’s HARD.
Just sit tight. And good luck!
I’m in the same boat as Kat; my heels are narrow in proportion to my forefoot, so in tights, pumps tend to fly off my feet. I’ve always done strappy heels or boots most in the winter, but I may have a new solution. I just put pedag’s “Girl” anti-slip pads in two pairs of pumps, and they are life-changing (despite the name)! I tried them with tights, although not for a full day, and I didn’t walk out of them. I’m getting pairs for all my pumps now.
The anti-slip heel pads are awesome! I have them in nearly all my heels — whether I wear tights or not, my heels slip out of my shoes. I already wear a 6.5 which is hell to find to start with, so now I can customize pretty much all my shoes to fit! YAY!!!!
Which reminds me…. I should stock up for fall/winter. Occasionally you do have to replace the darn things.
I just like how strappy shoes are cute and a bit different without going off the deep end.
Apropos of nothing, I love the “wear a suit at least once a week” advice. Had a big presentation today; wore a suit; looked both presentation-appropriate and like “me.”
I actually think most of these wouldn’t look good with tights — the ones without edges are too “summery” to wear with tights.