The Next Step: Shoes

How to Upgrade Your Shoe Collection | CorporetteWe’ve talked about upgrading your work clothes, buying better bags and grown-up furniture — but we haven’t yet talked about different tiers for shoes.  (Of course, we’ve talked in the past about comfortable heels, classic flats, which brands of shoes we love, which brands just don’t work for us, and even about how to find shoes for fussy feet.) I’m mostly grouping these by price, and only including brands that either I or the readers have noted as comfortable shoes — there are obviously a ton of brands that look pretty.  As with the other posts in this Next Step series, this is more of a continuum than a definitive ranking — do you agree with the shoe continuum? Are we missing any major brands?  Without further ado…

Bucket 1: Budget Shoes

(generally under $75, either with their MSRP or a frequently-on-sale price)

Bucket 2: Midlevel Shoes (Trendy)

(mostly known for style, but also reportedly comfortable)

Bucket 2: Midlevel Shoes (“Comfort”)

(mostly known for comfort, but also some stylish or classic picks, generally under $200)

Bucket 3: Upgrading (Trendy)

Bucket 3: Upgrading (“Comfort”)

Bucket 4: Splurges

Ladies, what do your tiers look like — which shoes are worth the splurge? Which budget shoes to you like?  Which tier makes up most of your collection — and if you’ve moved through different tiers, when and why did you upgrade (or fall back to a previous tier)?
How to Upgrade Your Shoe Collection | Corporette


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The Next Step: Shoes


  1. LilyStudent :

    I struggle with spending more than £70-100 on shoes, I think because they go on the ground. Most of my shoes are from Clarks.

    • Same. I have to walk on pavement a fair bit and most of our floors are tile. It kills the heel tips of my shoes. The nicer, more expensive shoes I have I try to wear very infrequently.

    • wintergreen126 :

      I’m the same way. The more expensive shoes rarely show face. The shoes I wear daily will be worn until I wear them into the ground.

    • I walk on concrete, uneven roads and dust so comfort is key. I make sure to update my shoe collection twice per year but I have about 20 shoes total (including boots and running shoes).
      A quick look at my shoe collection gives this:
      02 Clarks: black pumps – Flattish shoes
      02 Sofft: pumps in black and brown
      03 aerosoles: burgundy booties – black flat booties – colorblock pumps
      I also have shoes boots from other brands such as Aldo (uncomfortable) and Comfort Plus or Dexflex by Dexter both sold at Payless.
      But I find myself gravitating towards Clarks and Aerosols. Every time I rotate a pair of shoes out, I see that the replacement comes from one of these 2 brands.

  2. Mix of 2 and 3, mostly purchased with at least some promotion (e.g., friends & family at a minimum). 1’s tend to look cheaper to me and show wear far faster, so I skip them except for commuting shoes that will get beat up regardless. Although 4’s are beautiful, they rarely go on sale, and in any event I’d rather have four pairs from categories 2 or 3 than one pair from category 4.

  3. Team Taryn Rose :

    I am wearing pair of 3″ heels from 2006 but have many mid-heel and flat pairs. Comfortable and so worth it.

    • Wearing my Taryn Rose boots today (that I think AIMS found for me last season, thank you!). Super comfortable, only complaint is not much traction on the sole so I can’t wear them on icy days.

  4. I’m a shoe girl, but I don’t get Louboutins. Other than the red sole, they’re not aesthetically interesting, seem less well-constructed than similar Prada pumps (which can be near-identical in appearance but for said sole), and I find them enormously uncomfortable.

    AGLs are VERY comfortable, but generally (in my opinion) dowdy. I wear them for commuting but take them off as soon as I get to my office. And I dislike Tory Burch just in general – it telegraphs arriviste to me.

    I wear a lot of Ferragamo (which, by the way, I think would probably constitute a splurge for most people – my pumps are typically $450-500, which isn’t significantly less than your splurge bucket) and LK Bennett, with some Ivanka Trump thrown in for fun trendy stuff.

    • I wanted a pair for a little while but was quickly dissuaded after trying them on. I wear 4″ heels to work every day, and I could not walk three steps in those shoes. Since then, I’ve decided I don’t really like the red sole anyway. It seems overdone. But the first problem was how awfully uncomfortable they were.

      • Eh, I think Louboutin comfort is a varies-by-foot thing. I’ve worn a brand-new (as in, not broken in at all) pair of 100mm (~4″) patent Simples to a wedding where there was much walking to the church downtown, then walking to the reception, and dancing on concrete at the outdoor patio reception. I wore them for 10 hours total, and my feet didn’t hurt until the walk home. And I wear flats 95% of the time, so it’s not like my feet are used to heel torture.

        • Anonymous :

          Late to the party, but: Agreed. My Louboutins are the most comfortable heels I own – they are just about the only work shoes I don’t kick off automatically under my desk – and my Simple pairs (one black, one nude) have held up as go-to workhorses for YEARS. Thinking about it – I bought these at least 6-7 years ago and they are still going strong (with the red sole replacement, of course). They were a little snug at first, but after an afternoon of wearing them under my desk, they literally molded to my feet. Love. Them. Then again, I haven’t ever bought the 4+ inch loubs, mine are all fairly practical lower heels (3″-3 1/2″ simples, or kitten heels)

          Pradas are great, too, but they don’t seem to want to stay on my feet. They’re beautiful, though. Love my Valentinos but the 4+ inch rockstuds are not the most comfortable (though the fact that I can walk around in them just fine is saying something, as 4+” heels are not my thing; and I still really love them). My Miu Mius are so uncomfortable that I never wear them, they have never broken in even a little; I will never ever buy another pair of their shoes. Can’t find a good fit with Guccis, gave up. I want to like Ferragamos – great quality – but I’ve never found a pair that both looks and feels good.

          I have been wearing my Jimmy Choo boots pretty much every day as my daytime shoes since it got cold, and I wore them pretty much the same way last winter. Commuting to work during the week, all day on the weekends, and if I’m being honest the commuting shoes often become my all-day shoes because I can barely make myself take them off. I don’t have any of their heels though. Somehow they are never my favorites. No Manolos, either.

          Agreed w cbackson re Tory Burch – that is right on. I have a pair of her Reva flats that I absolutely loathe. Insanely uncomfortable, even after being stretched out by the cobbler twice. I finally gave up this year and bought the scalloped Chloe flats in the same burgundy color, and really love them. Another amazingly comfortable shoe.

          I have a lot of shoes. At this point, I really just buy the occasional Bucket 4, and supplement with Bucket 3 (Stuart Weitzman/LK Bennett/Cole Haan) or J. Crew or the like for everyday trendy. I really need to do a closet purge of the bucket 1/bucket 2 items from earlier years but I just haven’t had it in me.

    • Agreed. And what a perfect use of “arriviste.”

  5. I hadn’t really thought about it before, but I do a mix of level 1–love the Payless Karmen and also have some Nine West that I don’t love and then level three trendy–L.K. Bennett (love) and Kate Spade Karolina.

  6. My heels are mostly bucket 4, except for a pair of basic black LK Bennett pumps. Flats are a brand not listed above but probably bucket 4, with some random Loft/DSW pairs for weekends. They’re not nearly as comfortable or long lasting though, so they’re mostly in random patterns or colors to go with a specific outfit.

  7. My splurge shoes are Gucci (which I usually hunt for on sale at the Bucket 3 prices). Wedges, pumps, and flats – they hold up extremely well and the ones I select really don’t go out of style. I’ve also got an assortment of Bucket 2’s and 3’s I wear often (Cole Haan, Brooks Brothers, and Kate Spade probably making up most my shoe collection). I spend more but will keep them for years, get them re-soled, etc.

  8. In the comfort world, I loved my Beautifeels. And I tried on a pair of Gentle Souls recently – my god, the most blissful foot feel I have ever felt:).

  9. A professional woman :

    I am solidly bucket 1 with a bit of bucket 2. I constantly rip the heels of my shoes and I hate messing with changing shoes every time I go outside, so I like owning more “disposable” shoes. I hardly ever pay full price for shoes either. I wear Nine West, Anne Klein, Enzo Angiolini, Franco Sarto, Seychelles, Banana Republic, etc. And I will NEVER pay over $100 for pumps. Usually I pay far less.

    • +1

      Also, generally, I’d hesitate to put Naturalizer in the same group as Rockport. I’d buy a Naturalizer pump over a Rockport pump just because of the price tag.

      I never spend over $100 on shoes, ever. I think the most expensive pair I ever bought was maybe borderline $80. And I usually buy shoes when necessary – as in, when my current pair of shoes dies in some way. Which is why I don’t have more than one pair of black, closed-toe pumps. I have bought shoes only if I don’t have a certain style that I think is necessary staple – like I bought a pair of black peeptoes because, well, I didn’t have any peeptoes! :) I’m solidly in the Bucket 1 category. And I must be a violent walker or something so it is probably a good idea I am in Bucket 1 where a dying pair of pumps is less painful than a dying pair of Bucket 3 or 4.

      And for the record, I work in an office where I’m the only attorney who wears heels.

  10. If you’re into bucket 4 and in NYC, Varda is AMAZING. Manolo quality but in conservative styles that are perfect for the office.

    • Second Varda. Extremely well made, which means: (1) very comfortable and (2) last forever.

      • Actually, I’d be interested to read about what makes for a well-made shoe, rather than a list of brands. I know how to look for well-made clothes but not so much shoes, especially when so many can be legitimately labelled ‘handmade in Italy’ and in fact be produced by migrant workers in Chinese-owned factories outside Milan with cut-rate leather. Men’s shoes are easier – ‘good year welted’ and other terms do actually mean something specific.

        • I find it easiest to answer this in the form of why I like Beautifeel since I have limited understanding of how a cobbler would describe the features I like. Here’s what I love about the Beautifeel booties:

          They have steel shanks — sets off the airport security, but worth it because it means the shoes absolutely hold their shape over 100s of wearing.
          Foot support — they encase most of the foot, so you have stability when walking on uneven streets.
          Adjustability — the elastic inserts allow foot support with the ability to adjust to the width of your feet
          Heel you can walk in — the heels have a base around 1″ in diameter so your foot is stable.
          Good communication — Beautifeel is precise in giving heel height, so you don’t accidentally buy something too high for comfort.
          Leather quality — the leather is smooth, attractive, but not thin — so it wears extremely well. The shoes can be polished, but rarely need to be.
          Construction — seams are beautifully contoured and double stitched for strength.
          Simple design — I won’t pretend Beautifeel looks like Prada, but the shoes are simple and elegant.
          Size stable — if you wear a 39, every pair will fit you the same way. You can shop on line.

          • A lot of these sound like aspects of design (the enclosed design of a bootie, the low heel) and brand management (consistent communication and sizes), rather than quality in the construction, but thanks anyway.

  11. Galo Shoes :

    Any other Galo shoes wearers? So surprised to see them close. Has anyone found a good replacement?

  12. Maddie Ross :

    I am the biggest Platswoon fan. I have found them to be super comfy as well as stylish. I have a ton of heels and was previously really wed to the Ann Taylor “perfect pump” and “perfect platform.” Now that they are not using as quality leather, I’ve moved away from AT though.

  13. I’m confused. Brooks brothers and Cole Haan are pretty much the same price but in different buckets

    • West Coast :

      Agree, Cole Haan is more of a bucket 2. I would definitely not put them in the same bucket as Stuart Weitzmans or Ferragamos.

  14. If I’m a Cole Haan fanatic, what should be the next brand I should step up too?

    • anon-oh-no :

      Stuart Weitzman. Not that much more expensive in general (regular prices around 300-350, but can often get on sale).

      • I am firmly in bucket three. I wear a size 10.5 or 11.0 N, so my options at lower prices Do not exist. Stuart weitzmans are comfortable and stylish; love Ferragamos, they have become pricey, but I have some Varas and Varinas that I love. I also like Amalfi and sometimes Van Eli’s. All have comfortable options…I work in retail and spend a lot of time on my feet.

  15. Little Red :

    I guess I’m Bucket 2: Mid-Level (Trendy) and Bucket 3: Upgrading (Trendy) shoe shopper. Interesting, I wouldn’t have put Ferragamo into Bucket 3. It’s only their very basic shoes (plain black Vara) that are under $500, most other styles are over that price point.

  16. Strictly a bucket 4 girl. I’ve mentioned this before on a previous post about tiers of bags, but this kind of stuff does matter and others do notice. I have overheard plenty of women execs commenting on so-and-so with the latest Valentinos or the Louboutin Pigalles or So Kates, etc. Again, I’m not condoning it nor am I condemning it. I’m just stating what I’ve experienced. Keeping in mind, again, that I’m in PR (not an uber corporate law firm), so perhaps things are different in my industry.

    On a personal note, I love a good shoe and I feel a marked difference in my comfort and quality when I wear pumps that are not top notch. If I’m on my feet all day, running press up and down a red carpet or so forth, that is priceless.

    • Blonde Lawyer :

      Depends on your location too. A lot of people where I live have never heard of 80% of the high end brands.

      • It depends where you live. I live in a walking city that gets snow. People tend not to wear shoes that they wouldn’t want to get caught in cobblestone or get salt on

        • I’m in NYC. People wear these to everything.

          • I think it’s more an industry than location thing. PR people wear them to everything. Public interest lawyers, even in NYC, do not.

      • I live in Pittsburgh where anything above Bucket 2 is probably considered expensive or splurgey by most people. Granted, I work in construction/engineering, which isn’t exactly the pinnacle of fashion, but I work downtown and rarely see people wearing higher end designers while I am out and about.

        I personally have mostly Bucket 1 now, but am slowly upgrading towards better quality Bucket 2/3 when I need to replace items.

    • Anon Lawyer :

      I agree with the industry thing – I ended up in a conversation with some of the male partners a couple weeks ago about Louboutins and they were stunned when they heard the prices. I think they would definitely have some questionable judgments (not saying they’re warranted) if I showed up with a pair.

      Part of me wishes I was in an industry where it would be a good thing that I wore designer pieces – I try really hard not to make my wardrobe look like I spend too much on clothes.

    • I’m in DC (law) and no one I know cares about, or even seems to know about, brands like that.

      • A professional woman :

        Agreed. I am in DC too and no one wears super high end anything. Our NY office is another story – the women up there carry Celine and Chanel handbags and wear Louboutins all the time. But here in DC, we carry Kate Spade and Michael Kors and wear Bucket 1 and 2 shoes on our feet.

        • That is my experience as well. Celine, Chanel, Louboutin, Jimmy Choo, Prada, and Burberry trench coats. Anything less is looked at as being “unsuccessful” or “not in touch”.

          • And actually… it’s quite stressful to stay competitive and “dressing the part” in this environment.

          • Interesting, since some of those brands seem significantly overexposed (and therefore, no longer “in touch”) to me.

        • In my city, Kate Spade is considered high end. The only person I know who has a Kate Spade purse always rushes to say that it was a gift when someone notices it, because she doesn’t want anyone to think she bought it for herself. If I did wear Bucket 4 shoes or a purse, I don’t think anyone would recognize them, but if they did I don’t think it would reflect well on me.

          • I find it hard to believe that there are not many successful female lawyers, even in NYC, who do not wear Bucket 4 shoes and who frankly do not care if some other gossipy women are talking about their shoes or not. Believe it or not, you do not have to be the epitome of high fashion or spend half your assistant’s paycheck on shoes to be successful. I am sure that there are plenty of other successful women attorneys who would agree.

  17. Diana Barry :

    I mostly wear bucket 2, but my choices are really constrained by what brands are wide enough for my foot.

    • Sydney Bristow :

      Me too.

      I’d add Cobb Hill brand to bucket 2 (comfort). They are owned by New Balance and their flats have quite a bit of cushioning an support. I have a pair of flats that have lasted longer than anything I’ve bought in the last few years.

  18. Donald J Pliner are amazing. Big fan.

    • +1

      I have a couple pairs of DJP flat boots that are absolutely amazing.

  19. Manhattanite :

    I keep going back to naturalizers for heels. They are just so comfortable. I know they are ugly, but just too comfortable to pass up. I have one pair of rockports — lendra — that are very comfortable and slightly more on trend (skinnier heel, pointier toe). I have trouble paying more than $100 for heels. I tried cole haan’s after hearing good things on comfort, but they crunched my toes too much. I think my foot is too narrow at the middle, but not a true narrow.

    • I agree about Naturalizer. Many styles are ugly/ granny, but the basic pumps look just fine to me. I think they are well-priced for the quality, and they fit me well.

    • Naturalizer has been my go-to for work flats lately. And I don’t feel bad throwing them out when they are worn or stinky.

    • (Former) Clueless Summer :

      The Lennox pump is my go-to black pump. No, they’re not sexy but they are perfect for days when you need to be presentable but are walking somewhere with male partners who walk too fast, standing all day, out of the office all day (so no chance to change shoes) or any other day where foot pain or a turned ankle just won’t fly. I find them super sturdy and well-made feeling, plus the sole is a bit grippy, so you won’t slide on marble or wet sidewalks.

  20. I’m comfort bucket 2 all the way. My most worn pairs of shoes are Danskos, Clarks, and Birkenstocks. I got a relatively fashionable pair of Danskos, and wear them all the time, alternating with my Birkenstock clogs.

    It helps that a lot of the people I work with think that an appropriate transition from summer to winter is adding wool socks under their Birkenstock sandals.

  21. I’m an engineer working in an industrial environment so most of my day-to-day shoes are bucket-2 comfort Clarks. I wear heels very infrequently and but have a few plain bucket-2 heels comfortable enough to wear for the entire event but versatile enough to wear with lots of different outfits. (I saw someone at a wedding wear super-hot shoes to the ceremony and then switch to flip-flops the entire reception. It felt a little disrespectful to me that she didn’t stay in wedding-appropriate clothes the entire time.)

  22. I’m solidly in Bucket 2 (Trendy) for pumps/flats/sandals, but I will splurge on Stuart Weitzman (Bucket 3) for boots, because they look great and last for years and years.

  23. I have a mix of buckets 1, 2 and 3 (both comfort and trendy). My only non-negotiable is that have to be leather unless they’re some type of fabric (cotton, satin, etc.).

  24. Calibrachoa :

    I have been craving Fluevog shoes for years and years, but until I get to actually visit a shop, me and my strangely-shaped, canoe-sized shoes will stick to things I know will fit my really, really, REALLY wide feet – generally, Doc Martens (thank you, casual office!) and Evans shoes.

    Overall, I find myself sized out of most brands either in plain size of width or both :(

    • It’s worth the wait… I’ve been wearing ‘Vogs for 25 yrs and still get giddy going in to the store. Spend a couple of hrs & you’ll learn which lasts fit your feet. It’s worth planning a vacation around a shopping trip! The DC store is great, but Vancouver is always a treat.

      • Calibrachoa :

        My sister lives in Seattle so once I get across the pond to see her…. :D

    • I think Fluevogs tend to be narrow.

      • Calibrachoa :

        I’ve heard it both ways from people so that’s why I want to check them out in person.

  25. Anonylicious :

    I’m definitely a Bucket One/Two if it’s on sale person. I love shoes, but I have a hard enough time talking myself into spending over fifty on a pair. I think a hundred is my upper limit psychologically.

    Also, I keep misreading “Midlevel Shoes” as “Medieval Shoes.”

  26. I feel lucky in that Bucket 4 brands don’t make shoes in my size (10AA). So I’m not tempted to spend that much, ever. I’d add Sesto Meucci and Renzo Fontanelli, both of which make extended widths. I guess they are Bucket 3, though I always buy them on sale, so I’m not sure of the sticker price.

  27. anon-oh-no :

    This post is so up my alley; I’ve always been a shoe girl — the more pairs the merrier. though when I was younger payless was my go-to source. now I am a 3-4 bucket all the way. Of the 150 or so pairs I own, probably half are Stuart Weitzman, Manolo Blahnik, Prada, or Ferragamo. I have a few pairs of most of the others (Cole Hahn, Jimmy Choo, Kate Spade, Valentino, LK Bennett, and Miu Miu), but these 4 brands are by far the most comfortable, so they are what I stick with. I also find Enzos very comfortably and stylish, so I have a number of pairs of Enzos.

    I also just got a pair of SJPs that are quite comfortable and I think would fall into category 3.

  28. All my shoes are Ferragamos, Stuart Weitzman or Bally. I once owned a pair of python Gucci heels that were so comfortable that I literally wore them out. I will spend money on shoes but…never, ever buy (even good shoes) unless they are discounted/on sale. I feel “good” shoes are more important when “success” dressing than a handbag.

    I am not impressed with “red bottoms”. My Mother-in-law gifted me a pair for Christmas one year. I’ve wore them twice…totally uncomfortable on my feet, the red soles seemed to wear easily and I kept stumbling in them.

  29. I’m glad you did this post on shoes. Can you do one for Professional boots? I’m having a hard time finding something that will fit under my work slacks that don’t have a high heel.

    • I second this. I have Raynauds and I’m in Chicago so I need to wear thick socks in the winter to keep my toes warm otherwise I lose feeling. I’m also 5’11” and not interested in heeled boots because I don’t feel like being 6’2″+ or finding longer inseam pants. I recently tried Fitzwell Julie Booty from Zappos and the quality and fit seemed lovely. I also tried Sam Edelman Petty which fit just like my Penny boots so they also felt amazing but the heel was a tad bit taller than I wanted. The slightly higher heel did look good with the pants. Created the illusion of an even higher heel.

      I like the look of taller boots with skirts but this goes with my need to be warm.. I prefer my legs covered. That way I can layer with leggings underneath. I’m very cold all the time

  30. GoldMedallion :

    Bucket 3 purchased at Bucket 2 prices. I very rarely buy Stuart at full price and wait for discounts/specials/stalk the designer shoes at Off 5th/Nordstrom Rack. I do have one pair I bought full price (Fever cognac) because at the time I wanted them so badly I could hardly see straight.

    I have one pair of Loubs I got at a consignment shop and found them to be strangely comfortable. I’m in NYC and work in financial services (as a consultant), so seeing a 24 year old at a client who probably spent half her rent money of her Upper Upper East Side walk-up on a pair of Loubs is, while ridiculous, not surprising. My purses are Gucci (consignment) when I carry them, but I usually carry a wristlet (I hate big purses!) tucked into my Tumi bag, purchased on sale and b/c it kept my stuff better organized (and looked more professional to boot).

    I have noticed that if I’m good to my shoes, they last a very very long time. Polish, heel replacements… I bought a pair of patent leather Delman flats in 2007 and they still look brand new.

    Boy do I wish I could wear Birk’s and wool socks at work…

  31. I love my Fluevogs and have been buying them since there were just a couple of stores in Vancouver. The “Promise” is the most comfortable heeled shoe I’ve ever worn and never fails to draw a compliment. I loved the short “Malcolm” boot so much that I have it in brown and black–another compliment magnet. Same story for the higher shaft boot named Oscar. They always have 2 great sales a year , you can often save 50% if you have the patience (and guts) to wait for the prices to drop. These shoes are beautifully made and last for years— I’ve got a couple of pair that are older than my interns!

  32. Just wanted to suggest adding Banana Republic to this list – they make excellent shoes. They are appropriately stylish, comfortable (always have cushioning on the bottom no matter how high the heel), and last forever. They are also very affordable – I would say bucket 2. I have three pairs in rotation right now, and have had others in and out over the years. They are one of the first places I look for shoes now. Beyond that, I’m basically all bucket 2/trendy – I have a few pairs each of Coach, Calvin Klein, Sam Edelmen, and Via Spiga. I also have some more designery shoes, but most of those are from DSW when they had the designer section.

  33. This post couldn’t come at a better time. I’m currently looking for black pumps, no more than 2.5 inch heels that are super comfortable because I stand for 3-4 hours each day. From either buckets 1, 2 or 3. Any suggestions?

  34. Mostly bucket 3, driven by foot issues. Stuart weitzman, cole haan and Ferragamo are all great for wide feet…I have found. For weekend wear, I like l’amour des pieds. The most comfy sandals I own. And they’re pretty too.