Stylish, Comfortable Shoes That Are Made to Last

Salvatore Ferragamo Carla Pump | CorporetteFor some women it makes more sense to splurge on “investment” shoes for work that (hopefully) you can wear for years, rather than choose cheaper ones that you’ll keep having to replace. Reader M wonders:

I am struggling with my shoe game! I would like to invest in shoes that are stylish, comfortable, and long lasting. I notice that guys purchase one expensive pair of work shoes but they last their entire careers. I work in the finance area in a young company. Have you seen any gems lately you would like to share?

I’m curious to hear what readers think here, because I have mixed opinions about this. First, the “classic” black pump does change — right now toes are pointy; in recent years they were almond-shaped instead. Second, beware of pregnancy, aging, and feet — many women find that their shoe size will change throughout their lives. Personally I gained about a half size with each pregnancy, which — after having to donate the vast majority of my shoe collection — makes me happy I never committed and spent the money on that pair of Manolos or Choos. Even just with aging, your arches may fall and your feet may widen. So: I kind of don’t believe in “lifetime” shoes for women.

That said, I do think that a well made shoe is worth your money and will last a lot longer than most inexpensive shoes, particularly with proper shoe care — and I generally think they’re more likely to be comfortable heels. If you apply our fashion math to neutral shoes you wear 1-2x a week, the cost per wear really does come down significantly. We recently rounded up black pumps for work, as well as beige pumps; the following brands and particular styles are ones that I see readers note over and over again as being worth the splurge:

If you’re a fan of flats, definitely check out AGL flats and the Ferragamo Varina. In a slightly lower price point, I’ve continually heard readers praise Brooks Brothers shoes (right now these leather pumps are marked to $59-$124), and while the newer Cole Haan shoes are getting mixed reviews, you can still check out eBay for older Cole Haan Air shoes at a steal.

Readers, what are your thoughts on “investment shoes”? Which brands and styles are your favorites? Where did you start; where did you draw the line? How long do you expect a pair of investment shoes to last?  

(Pictured at top: Salvatore Ferragamo ‘Carla’ Pump, available at Nordstrom for $550.)


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  1. Cosign the Stuart Weitzman platswoon. Always look polished and they last for years as long as you get the heel taps redone. My old pairs with shredded heels become pants-only heels. So comfy and such good quality.

  2. We are going to a wedding next weekend and the couple isn’t registered anywhere. They are good friends, and just writing them a check isn’t sitting right. I ordered an engraved bottle of champagne with their names/wedding date and want to include something else. Ideas? Or is that plus a check right? We are suburbanites with a young family and they are still the jet-setting city dwellers we once were :)

    FWIW we are in a HCOL but the friends marrying are well off, well established in their careers and mid 30s– that’s part of why the check feels funny. They are going somewhere tropical for their honeymoon but didn’t even register through “honeyfund” or the like- so there isn’t a “buy a [x] for the honeymoon” type option.

    • Anonymous :

      Write them a check and call it a day. That’s what they want. It’s not at all weird.

    • too late to edit- just realized this is in the wrong thread. I will repost elsewhere!

    • Cash is the best gift. There’s only so much stuff anyone needs, and unless they truly have not established themselves as adults with a household yet, they don’t need things. They probably didn’t register because they’d really prefer cash.

    • Anonymous :

      I don’t disagree that they WANT cash, but I think it’s incredibly tacky to basically ask for cash by not registering or giving the name of a place for donations. If it were a young person just starting out, I’d roll my eyes and cough up the cash but when the person is mid-30s and very well off, something about being asked to give cash really rubs me the wrong way. I’d probably just pick a houseware gift. It may not be what they want, but that’s what they get for not registering. Alternatively, if you know where they’re staying on the honeymoon, you could send alcohol to the room, arrange for a romantic dinner on the beach, or give them gift certificates to an activity you think they would enjoy (e.g., sunset boat cruise).

      • Anonymous :

        Nope! They aren’t asking for cash! They’re just indicating that there are no particular housewares they need. This is 100% not rude. Please do not let your own needlessly curmudgeonly preferences make couples thinking of doing something perfectly appropriate reconsider. And by all means get them a giant metal chicken if that’s how you show your love, but not registering is 100% A-ok.

        • This is why no one can win when it comes to weddings. If a well-off, established couple in their mid-30s had registered somewhere, someone else would be commenting about how tacky it is for a couple to have everything and still register for more gifts.

          • +1.

            If I care enough about you to attend your wedding, then I will buy you eight pairs of fluorescent orange sneakers if that is what you registered for.

            When did the shift in impressions of wedding registries/gift suggestions go from “This is a useful tool to make sure couples receive something they really want” to “HOW DARE YOU INDICATE YOUR GIFT PREFERENCE?!?!”

          • +1, As someone getting married next week (although admittedly as part of a not-well-off couple), I am really turned off by your approach to, and judgement of, your friends’ wedding.

            How is it any more or less tacky to ask for gifts via a registry (which you would spend cash on either way)? I really do not understand the logic here, at all. If they are well off, they don’t need your honey-fund contribution any more than they need your cash contribution. Do they really need you to pay for some tourist-trap dolphin swim or dinner at their hotel? And most people live together before marriage anyhow and already have everything they need for the house regardless of income level.

            I think a cash gift is implied to help pay for your ‘seat’ at the wedding to offset costs. You think people didn’t sign checks at the wedding of Ivanka Trump or Chelsea Clinton? Give me a break.

      • “but I think it’s incredibly tacky to basically ask for cash by not registering or giving the name of a place for donations. ”

        Wouldn’t it be tackier to register (when they don’t really want / need anything) and/or give the name of a place for donations — which suggests that they expect you’d be giving a gift? I

        • Anonymous :

          If you say “we have everything we need, no gifts please” I agree it’s not tacky (and that’s a classy way to do it because you’ll probably still get gifts from a lot of people). Otherwise, no, still tacky because a gift is expected and if you don’t say “no gifts” and you don’t register, you are asking for cash.

      • “If it were a young person just starting out, I’d roll my eyes and cough up the cash…”

        So pretty much a cash gift is ‘tacky’ to you regardless of the couple’s income level. The couple has to pay ~$200 for you to attend but instead of helping the couple pay for their wedding and avoid debt, you still rather force clutter on them that they don’t need regardless? If this is your approach, you shouldn’t attend weddings at all. I wouldn’t want curmudgeons like you at my wedding if this is your level of anticipation of the event. No need to eye-roll or cough up anything… just stay home and save the couple the busywork of returning your Tiffany gravy boat!

    • Must be Tuesday :

      Or skip the gift altogether. They didn’t register because they don’t need anything. Go and celebrate with them. They invited you to the wedding, so your company is what they truly want.

    • Maybe I’m weird, but I am reading this as the couple genuinely does not want presents. They are a dual-income, well-off couple who are merging households… what do they want, their friends with kids, single friends trying to make a go of it, or friends in non-profits (or less remunerative careers) to run up their credit card bills buying them stuff?

      If you feel really weird about it, buy them really great baby gifts if/when she gets pregnant. Otherwise, don’t worry about it.

    • I always feel strange giving cash to people who are already well off or very close friends. I think a bottle of champagne is perfect. If you don’t feel its enough maybe a gift card to a great restaurant or tickets to something that they are known to be interested in.

      • What is so strange about it? Did you not want your friends and relatives to give you money at your wedding (or would you not want it at your future wedding)? Would you really rather receive 100 pots, pans, toasters and vases?

        If everyone takes this advice, the couple will be swimming in booze and have an overflowing calendar full of social obligations to people who found it too ‘strange’ to sign a check to their loved ones.

    • I’d suggest taking them out to dinner somewhere fun and footing the bill. Maybe add tickets to a show if that’s more along the lines of the amount you intended to gift them. I had a friend take me and my husband out to a spectacular dinner as a double date with her and her husband for our wedding present, and we had an amazing time and delicious food and wine. I don’t remember who bought us random appliances and knick knacks for our wedding, but I do remember how much fun we had dining with our friends.

  3. Anonymous :

    Guys don’t purchase one pair of shoes that lasts their whole career. Like, not at all. Many of them repurchase the same style over and over but not like one pair forever.

    • Anon tax lawyer :

      Also a guy thing (and a me thing): buying a pair in multiple colors

      • +1. I like Ivanka Trump pointy toe flats. I wear them almost daily. I have one pair of black and one pair of camel in current rotation, and two extra brand new pairs of each color sitting in boxes, waiting for the current model to wear out.

        • Cardi love :

          Oh I was just looking at these. Are they comfortable?

          • I love these too! I find them very comfortable. I wear the black patent leather pair almost every day, and like Anon above I keep a back up box :)

          • Super comfortable. I’ve been wearing them for probably the last 5-6 years (not the same pair, obviously). Huge thumbs up.

        • ooh, thank you for the tip! do these run true to size? I’ve been looking at a pair and debating which size to order.

        • Are you talking about the “chic” flats? I’ve been eyeing them, but also hadn’t pulled the trigger.

      • I bought a Söfft pump in black and brown and they were my workhorses for 2-3 years.

    • Mountain Girl :

      Just bought my first pair after looking at them for several years and skipping over them – not exactly sure why. But they are really comfortable and I should have taken the plunge much earlier. They are great shoes and I highly recommend them.

  4. I have started wearing Cole Shaan grand os oxfords, which are sneakers that kind of look like oxfords. I am to the point where comfort is my main priority. If someone would design office-appropriate Birkenstocks, I would be so happy.

  5. Anonymous :

    This is why I splurge on handbags not shoes. Plus they’re easier to keep in good condition.

  6. I don’t think shoes are ever investment items. Women’s heeled shoes will never last as long as men’s shoes because the soles are thinner and the heels are easily caught in grates, cracks, etc. Also, styles of women’s shoes change quicker. To me, the SW Poco looks incredibly dated.

  7. I think the most important thing is to make friends with your cobbler and have him treat your shoes before you even wear them. Every pair of shoes I’ve done that with has lasted me a lot longer and I walk a lot in all seasons and am pretty hard on my shoes. That said, I have learned the hard way to not spend too much on shoes with certain details like leather wrapped or embellished heels in hard to match colors, etc., because no matter how much I try it’s just too easy to ruin the shoe in a grate or a crack in the sidewalk. I have one pair of croc-embossed heels that I’ve made into indoor shoes that I basically only wear at the office, but where’s the fun in that?

    I do like to “splurge” a bit on a well-made pair, but even my “splurges” tend to be on major sale. I think the most I ever spent was ~ $240 on a pair brown suede Givenchy kitten heels. I’ve managed to find other brands (Miu Miu, SW, Ferragamo) within or even well under that price range as well. I also can’t bring myself to pay full price for lower priced shoes, somehow that feels like it is more of a waste, if that makes sense.

    • This is such a smart comment, I have very littel to add. I alway’s get shoe’s ruined in the city, whether by stepping into grate’s or scuffing them against the curb, or catching dog poopie on them, so I now wear Nike Air’s to work and to court, then change into my good shoes once INSIDE. Mason carries my shoes when I go to court, and the ONLEY time I have to wear my shoes out is when I go out to lunch with the manageing partner and a cleint in the middel of the day when I can NOT carry my shoe’s and wear my Nike Air’s. FOOEY b/c that is when I ruin my shoe’s.

      The best shoe, therefore, are Nike Air’s. I walk and my fitbit registers every step and dad is happy b/c he sees the result’s with my tuchus getting smaller! I hope to have a tuchus like Rosa before July 4. YAY!!!!

  8. I really, really love that Brooks Brothers shoe with the asymmetrical vamp. Do their shoes tend to run narrow or wide? Suddenly I’ve become a 9.25 instead of my normal 9. 9.5s are usually too big but I’m struggling with toe crush.

  9. Anyone have luck breaking in Ferragamo heels or flats? My mother has gifted me two pair–both flats–because she thinks they should be the ideal professional shoe (she doesn’t wear them…she’s retired and mostly in casual wear). I find them extremely uncomfortable. Length-wise and width-wise they should be fine, but the leather is SO STIFF. Wearing them all day makes my feet ache! Any tips on getting them to be more comfortable?

    • I have two pairs of Varas in patent – one pair of flats and one pair of kitten heels. You just gotta keep wearing them around the house and one day they will mold to your feet. I used to wear them while watching TV.

  10. I love Taryn Rose. I have the same style in black and brown and they are basically all I wear with suits. They are a splurge (for me), and the brand doesn’t always offer classic pump styles every year, but mine have lasted a very, very long time. When I realized how well my original pairs were working, I invested in another pair of each color.

  11. Tod’s for life, especially if you get the shoes with all rubber soles (cf. the gommino drivers).

    I got my first pair when I was 18 and wore them year after year. Still wearing them now (just dropped them off last week at Leather Spa for some cleaning), and I am almost 30!

  12. For those willing to go with flats I warmly recommend E Porselli ballerinas. They are so very comfortable and look amazingly good. I bought 3 pairs so far (black stone and powder) and wear them with dresses to work every day!

  13. I totally agree with AIMS. Make friends with your local cobbler! Some of my most beloved – and classic looking heels – aren’t designer shoes at all. In fact, I purchased some at DSW, but thanks to my shoe repair guy – they still look brand new (and expensive). A good polish, repair and heel tip replacement will do wonders!

  14. Anonymous :

    I love my Varina flats; however, after one season’s wearing, they are shot — I’ve worn through the leather soles. That being said, this is a small price to pay because as much as I’m on my feet (lawyer/lobbyist), I never felt crippled this spring like I would have if I’d been in heels in the marbled-hall Capitol. It hurts to pay this much for shoes, but it hurts more to hobble around on sore feet all of the time.

    • Have you considered getting your Varinas topied? It will prevent the soles from wearing out so quickly.

      If that’s not for you, then check with your cobbler about getting them resoled if the rest of the shoe is still in good shape. You would be surprised at how much a good cobbler can save you :)

  15. I never used to “splurge” on shoes. I have difficult feet – wide in front but narrow in the heel, and it never made sense to me to spend a lot on shoes. After buying so many pairs of mid-priced shoes that ended up being uncomfortable or worse, I finally bought a pair of SW chic pumps, and they have lasted for years. They look the same as the day I bought them, and I can wear them all day without feeling any pinches, etc. Last summer I bought AGL low wedges to wear as travel and commuting shoes, as well as with more casual clothes, and I am in LOVE with them. Incredibly comfortable, look good, and have held up amazingly well. I recently was on a one-week work trip to Europe and did it with only those 2 pairs of shoes – the SW for work and dinners, the AGLs for travel and walking around the cities during my free time. Worked out amazingly well. I just bought a pair of Arche sandals and wore them all day, every day on a trip to Santa Fe – the most comfortable sandals ever created. So now, I’d say I am a convert to more expensive shoes, as long as they have the comfort and fit that I need.

  16. Decklededges :

    After seeing them on this website, I bought a pair of Ukies. They are amazingly comfortable and I’m hoping they release more styles. I’ve only had them for a few months (so can’t speak to whether they are lifetime lasting), but I wear them at least 4 days/week. They still look completely brand new. Worth every penny.

  17. Looking for experts help identifying brand sole marke SWSWSWSW made in Spain – women’s thigh-high boots

    • I am no expert but I have a pair of Stuart Weitzman chocolate brown knee high stretch suede boots (8.5M) that have SWSWSWSW on the sole. Inside there is a tag 3W 39386. I purchased them at Saks Fifth Avenue.