A Newbie’s Guide to Designer Shoes

If you’ve been ogling designer shoes but aren’t sure where to start (or whether to make the leap!), this post is for you.  I’ve been reading Tiffany’s blog at I am Style-ish for a few years now, and I’ve always admired the professional but chic way she incorporates designer shoes into her outfits.  She has quite a collection, so I asked her to write a “intro to designer shoes” post for Corporette.  Enjoy! — Kat

Hello Corporette readers!  It’s Tiffany from I am Style-ish here!  I’m so happy to be here while Kat is away enjoying time with her new little one.

I love Kat and Corporette for bringing together so many of us career driven, highly ambitious women.  I also love that Kat incorporates a lot of fashion and style in her blog because I know a lot of us still want to look our best while working our way up to the top ;) I’ve never sacrificed style for my career in HR and I don’t believe that you have to.  Along those lines, although I’m a very career driven woman, I also love fashion and if there is one thing that you need to know about me is that I love shoes.  Not just any shoes, really really tall shoes and preferably with a red sole ;)

a few from Tiffany’s collection!

My first pair of designer heels was a pair of Jimmy Choo pumps that I thought were beautiful and when I wore them, I just felt fabulous!  I caught the bug for designer heels after that pair and I just haven’t stopped.  Even though I worked at a conservative IT Consulting firm, I never felt weird about wearing them, in fact, I got more compliments on my shoes at work than I ever expected!   (In my current position as Director of Operations for a consulting firm, I work from home a lot, but my designer heels always come with me when I travel for meetings.)

I get a lot of questions about designer shoes, what to buy, how they fit, how to get them on sale and are they REALLY that much more comfortable so here are some things that I’ve learned.

Different designers fit very differently and you’ll never know which ones you like until you try them on.  I very rarely order shoes online unless I’ve tried them on before only because sizing can be so inconsistent.  In terms of comfort, my top choices are Miu Miu and Jimmy Choo. For very pretty but not very comfortable shoes, it’s definitely Christian Louboutin.  Dior, Prada and YSL all fall into the middle for me.  These all have exceptions of course as I’ve found that my Louboutin Simple 85 pumps (pictured below) are one of my most comfortable shoes (although in general, I’ve found that Louboutins are not that comfortable — but that doesn’t stop me from buying them!).

Christian Louboutin Simple 85 Suede Pumps

These Jimmy Choos are perfect for the office.  I own many Jimmy Choo pumps as I find that they have the most office appropriate styles.


Jimmy Choo Gilbert leather pumps

Or these Miu Miu pumps are gorgeous!  It’s a 5 inch heel but with a 1 inch platform and perfect for shorties like me that like to feel that we can be a “normal” height sometimes :)

Miu Miu Leather platform pumps

Having a hard time finding shoes in your size or on sale?  Befriend the sales associate!  This part is very important for a shoe lover like me!  When you are trying on shoes, let your sales associate know that you are interested in more shoes that are similar or by the same brand and also if they have a sale on designer shoes, please give you a call.  And then every time after that when you walk into their department, ask for them and buy all your shoes from them.  It’s a win-win partnership as you get the shoes you want and they get the commission!  I’ve had the same sales associate at Nordstrom for the past 4 years and he calls me every time he gets shoes in my size (I wear a size 5 which is a hard size to come by) and he also calls me when they have sales on designer shoes and I get to pick out the shoes before they go on sale to the public.  This in itself has saved me hundreds, if not, thousands of dollars!  If I had to wait for sales to buy my shoes, I’d be stuck with a lot of styles that I didn’t like or I’d buy a size up and try to put in extra insoles hoping it will fit (it never does, I’ve learned to only buy shoes in my size, no matter how much on sale they are!)

Comfort wise – I think that the comfort levels are different in designer and non designer shoes.  I do think that designer shoes are more comfortable because of the craftsmanship.  The insoles which are made with leather are much more comfortable and cushion your foot as opposed to non-designer heels which can be made with manmade materials and that are stiff and can feel like you are walking on a piece of wood. When designer shoes are uncomfortable it’s because the arch of the shoe may be a bit too high, which Louboutin is guilty of but that’s also why your foot looks so damn good in his shoes.  He does an arch like no other.  It’s definitely something that you have to get used to and I usually reserve those types of shoes for evenings when I know I’ll be sitting most of the time.  I’m not going to say that all designer shoes are comfortable but with my experience I’ve had very little issues of getting blisters because the shoe is rubbing me the wrong way.

Are you a shoe lover as well?  What brands are your favorites?

And if you’re interested in how I store all my shoes, check out my shoe closet video!


Interested in writing something similar for Corporette? Check out our guest posting guidelines.


  1. SF Bay Associate :

    What a great topic! I haven’t stepped up into the realm of true designer shoes like Tiffany, but I 100% agree that more expensive shoes are more comfortable. All of my work heels are Italian or Spanish made because I have found the quality to be so much better than China or Brazil. I would much prefer to have a quarter as many shoes, but only high quality ones, than the same amount of money in cheap shoes that hurt my feet.

    I have found that upscale shoes seem to run a bit more narrow than some of their less expensive peers. My work heels are Ferragamos (in wide for his heels, which seem to run a bit narrow for me), Kate Spades (great toebox space every time; note they tend to run a half size smaller than other brands), and Weitzmans (some styles run narrow, but are also often available in wide). They are well made, well balanced, and comfortable. Kate Spades are my absolute favorite.

    I’ve tried on Louboutins and did not get the hype at all. They weren’t that comfortable, especially for costing twice as much as Weitzman or Kate Spade.

    • As a fellow wide-shoe person, thanks for the advice. I find that my options are limited in wide shoes. Why must all shoes pinch me in the toebox, even when sizing up? Ugh.

    • Ditto on Kate Spade shoes – I also have wide-ish feet and find them the most comfortable shoes I have.

      On a funny note, my husband for my birthday thought he found a great bargain when he purchased a pair of “Louboutins” for me from some website in China for $150.00! Poor man…needless to say, they were definitely NOT real Louboutins. The overwhelming smell of rubber cement/glue when I opened the box about knocked me out! We still laugh about this, but it was a sweet gesture.

      • It has been on 60 Minutes ( aired twice) on China making famous fake brands like: Nike, Reebok, Juicy Couture, Prada, Micheal Kors, Versace, etc. The list goes on for miles. I avoid anything from China. I buy from India, Italy, etc when I can afford it, which is once in a blue moon.

    • I agree with Loubs not being that comfortable, but I do still want a pair, for which I judge myself. I really like Stuart Weitman, and I have heard great things about Ferragamos (like, people moaning when they talk about how comfortable they are). I have a couple of pairs of Kate Spade casual shoes but no work shoes yet. Her stuff is adorable, though, so I see it in my near future. I also really like Cole Haan, although those certainly don’t fall into the true designer category.

    • found a peanut :

      I don’t think Loubs are meant to be comfortable (although I have the same caveat as the poster – my Simple 85 pumps are really comfortable), they’re meant to be sexy. Many of his designs are also not office-appropriate, which means that I won’t buy them.

    • I love Kate Spade shoes – they are so comfortable. Cole Haan, on the other hand, not so much (for me at least).

    • MaggieLizer :

      Kate Spade and Weitzmans are my favorite higher-end shoes, too. I was hesitant about Kate Spades because they feel flimsy, but they’ve actually held up very well (although the heel cap that comes with them wears out faster than any other shoe I’ve ever had; I now get them replaced before I even wear them).

      The most comfortable pair of going out shoes I have are DVF’s Zia. I haven’t tried their work appropriate selection, but I’m keeping an eye out for any sales.

    • Has anyone tried stretching their CLs for a little more room in the toe box? I find my CL Simple 85s a little tight in the toe box but have been hesitant to take them to the cobblers. TIA!

      • found a peanut :

        Mine were also a little tight and I wore them with gym socks around my apt. One pair was literally so tight that I was losing circulation in my little toe, but after a few gym-socks wears they loosened up. I’ve taken other shoes to be stretched at the cobbler and have had very good results.

      • Mine always start out a little tight, but mold to my foot after a few wears.

  2. Beautiful shoes!

    I just found a perfect cardigan/blazer at Banana Republic. It’s a sweater that’s structured like a double-breasted blazer that’s substantial enough to not lose its shape. It’s in a dark gray and $98. It’s not online and the sales guy said it was selling out fast.

    It won’t work for more formal areas of the country but it will be a staple for me in the Silicon Valley.

  3. Nice Post!!! I also read Tiffany’s blog at I Am Style-ish. She really does have great advice on shopping for designer items. I’ve saved lots of money by using her tips.

  4. Nice to see you guest posting, Tiffany! I check out your blog periodically — you have a gorgeous shoe collection! You should amend your post to link to the video where you talked about shoe care (and bag care if you talked about it, I don’t remember) — I thought it was informative. I fear that I am developing my own addiction to designer shoes — and I love me my Jimmy Choos! Thank goodness the sizing is consistent!

    So this post was a pick me up from a pretty blue funk — particulary as I was going to be a ray of sunshine and share the following:

    1. While I am not a particular fan of the book, my heart sank last night when I read that NGDGTCO is going to be made into a comedy show. I’m sure it is going to spun as positive for women but, seriously, this could be bad — the main character is likely going to be a walking, cliched disaster. See http://www.tv.com/nice-girls-dont-get-the-corner-office/show/69237/summary.html.

    2. Added to that, I then saw a post about this lovely shirt for girls: http://www.care2.com/causes/jc-penney-pulls-im-too-pretty-to-do-homework-t-shirt-after-social-media-uproar.html. My face looked like this after seeing it –> :( . At least they stopped selling it.

  5. Diana Barry :

    I don’t have any fancy designer shoes – the fanciest I get is Cole Haan (from the outlet, usually). I can’t wear heels for any extended period of time (bunions), so I only wear them to networking events. I can’t really imagine spending $500 on a pair of shoes that I would never wear.

  6. found a peanut :

    I have a pair of Jimmy Choo Gilbert pumps (the ones shown above although I do not have them in black leather) and I actually find them kind of wobbly. It could be the material they’re made off – the leather does seem thinner to me than normal, which makes for very soft, comfortable, but unsupportive shoes. They are cute though, and I got them on sale.

    My favorite brands for shoes are Louboutin (but I promised that I would never buy a pair over 100 mm again, unless there is a platform involved), Bottega and Chanel for heels, and Chanel and Lanvin for flats (Lanvin flats are the most comfortable flats ever). I look forward to the day when I can just walk into the Barney’s shoe dept and buy everything my heart desires…

  7. Jimmy Choos were the most uncomfortable shoes I’ve ever worn. I got my $600 back for those, pronto. Stuart Weitzman, on the other hand, well worth the money for me, although like the previous poster mentions, they really don’t get worn all that often (business casual office)

  8. I pack my lunch for work every single day and translate the savings to a new pair of shoes every 8 months or so. Between Manolos, Loubs, and my Choos I would say I have been happiest with my Choos. The Manolos tend to cut up my feet a lot so strategic band aid placing is often necessary.

  9. housecounsel :

    Threadjack just to say that there is no dress in the world that doesn’t look better with my new Spanx cut-out bust bodysuit. And that I have never bought any shoes more expensive than Tory Burch, but someday I will have red soles. I will never buy Manolos, though, after I went into the NYC store a few years ago fully intending to buy some, and was treated like garbage, Julia Roberts in Pretty Woman style. And I was not wearing either a scrunchy or a fanny pack.

    • Having had 3 kids, I find the idea of a Spanx bodysuit appealing. But – and I’m honestly asking – can you/how do you pee without getting undressed. I’d hate to have to give up my coffee habit!

      • the full cleveland :

        There’s a “gusset” (i.e. an opening) at the crotch! No need to give up the coffee habit.

        However, I highly recommend against the Spanx if you’re going to eat anything that might make you a little gassy. I’ve never been so uncomfortable as the hours I spent in economy class, wearing Spanx, after a nice big salad with tons of black beans on top.

        • Not to get too far into the land of TMI, but out of curiosity do you actually use that gusset thing? On the rare occasion I wear spanx I always take them off to use the restroom. I just don’t trust it.

  10. a passion for fashion :

    I mentioned this last week, but ultimately try the shoes/brands on and figure out which ones work for you. Unlike some other posters, my Choos are my least comfortable, with coach a close second and faragamos just dont fit my feet well (they run very narrow, and in fact often carry extra narrow sizes for those hard to find sizes). but I have about 15 pairs of SW and 10 pairs of manolos and they fit wonderfully and are totally comfortable, even the 4-5 inchers. I also have 2 pairs of miu mius that are great. I have a couple pairs of gucci shoes that arent bad for 4 in heels, and a pair of D&G’s that I love. Oh, and i find prada to be very comfortable as well.

  11. I don’t wear high heels to work, and I love my Jimmy Choo and SW kitten heels. Both very comfortable.

  12. Totally unrelated threadjack PSA:

    I can’t vouch for ASOS personally because I haven’t ordered anything from them, but I just came across this website that has some potentially promising (longer-length & office-appropriate) dresses:

    tinyurl [dot] com [/] 3phqbg9

    • Corporate Tool :

      And now I am coveting the Ponti Midi Dress with Flared Skirt. 3/4 length sleeves+ modest neckline? I’m in.

    • ASOS is an amazing website. It is originally a UK thing and it became a very very expensive habit while I lived in London. While in London you could count on your package arriving within a few days, it takes much much longer here in the US (I think they are actually still shipping from the UK despite having a US website now). However returning things is insanely easy so I often buy several things with the intention of trying them all on and returning a few. Their actual ASOS line is pretty decent too!

      • As a newly pregnant lady, I also have to say I love that they have a wide selection of maternity wear that is cute, fashionable, (sometimes) work appropriate, and a lot more affordable than some of the other lines out there!
        FWIW – I got my package in the US from them within 4-6 days, and they processed a return in about the same amount of time. No complaints at all about the quality – for the price its nicer than H&M and about as good as Zara.

    • WHAT THE WHAT??? I love those dresses! How did I not know about this site?

  13. Thank you for this post Kat & Tiffany. I’m not quite ready to leave my DSW shoes behind, but I do have one pair of Stuart Weitzman’s and they are my tallest (and most comfortable) work heels. I can’t wait to try Kate Spade or Jimmy Choo next, and of course the red sole of the Loubi’s will always be enticing, even if they aren’t a 10 on the comfort scale.

    Kate – great idea about packing your lunch and rewarding yourself with designer shoes!

  14. I’m curious if Tiffany has any advice on vegan/ nonleather shoes. There are some beautiful choices now — it’s hard to know where to start.

  15. I just can’t justify spending that kind of money on shoes. One: I don’t have the budget. And two: I hate shoes. It’s the one item that I have real trouble with. I’m size 6 wide.

    But I’ve got a question. I’ve asked this of my friends, too. If you could afford to buy either a pair of Louboutins or a Birkin bag, which would you get?

    For me, it’s the Birkin, no question. I’ve always thought Loubs looked really uncomfortable and the rest of you have confirmed that for me.

    • I wouldn’t feel comfortable spending that much money on either item, but if pressed, I’d get the Birkin. If you take care of it, you can carry that sucker for decades and pass it down to your daughter. Can’t say the same for Loubs. Then again, Loubs are a fraction of the price of a Birkin, so putting aside the whole wearing out from street-contact and foot-contact issue, they can’t be expected to last as long.

    • MissJackson :

      I’m not ready to own shoes or a bag that cost more than what my car is currently worth. But I think that the question is a little skewed — because for the price of a (“cheap”) Birkin, you could buy 10 pair of Louboutins, at least.

      I guess I have a hard time suspending my disbelief, because (although I’d rather have a Birkin), I think “If I could afford to buy a Birkin, I would instead buy one pair of fabulous Louboutins and invest the other +8K!”

      I also don’t think that the two are comparable luxury goods. Lots of Corporettes have Louboutins (as evidenced by this tread!). While I’m sure there are some Corporettes out there that have a Birkin, it’s got to be a smaller number, right? (Perhaps none of us would ever fess up after the epic Birkin bag threadjack, though.) I think of Louboutins as something I might buy some day. I think of a Birkin as something I’ll probably never buy. Admitidly, this is all completely price dependent, so perhaps it’s entirely personal.

    • I have the money but this bag and shoe thing is completely lost on me.

    • I’m not willing to spend that much on shoes just because I’m very hard on my shoes. Walking around D.C., I often get the heels stuck in cracks. It’s painful enough when it happens to a pair of Cole Haans but I think I’d cry if it happened with a pair of Loubs and Choos.

    • I’d have to say Loubs. They just make me happy (though I don’t buy the sky-high ones – the lower-heeled ones are super comfortable for me).

  16. My dad gave me a pair of Prada pumps for my birthday, and ever since then, I’ve been lusting after another pair of designer shoes. I can wear them all day with minimal discomfort, and for 4.5 inch heels, that’s saying a lot! I also get more compliments on them than any other pair of shoes I own, and my girlish side loves the little gold charms on the soles.

    Unfortunately, I’m a mere 18 months out of undergrad, so they’re a little out of my budget for now. But it’s nice to have something to work towards (and maybe ask my boyfriend for for Christmas :p).

  17. Anon Canadian :

    I bought my first pair of high(er) end shoes this weekend at Marshal’s. These Tahari peep toes http://piperlime.gap.com/browse/product.do?pid=889247012&tid=plsp1r&kwid=1&ap=14 in red patent leather for $52 cnd!!Before these shoes my most expensive were from Nine West. I love the way high heel shoes look and I do own some but because I rarely wear them I don’t like to spend too much money on them.

  18. So disclaimer: spending that much for a pair of shoes kind of freaks me out (the most I’ve spent is ~$200 for Cole Haan), but ignoring that, I have a question for you ladies, especially those of you in law. I tend to find the Louboutin red sole to be a bit off-putting — I find it weird to essentially advertise how much one spends on shoes. (I find logo-covered designer bags similarly unappealing.) Do you think that there is any professionalism concern with this? Is a woman likely to be judged (positively or negatively) for wearing the recognizable red sole, especially a younger (late 20s/early 30s) woman?

  19. I bought a pair of sky high Louboutins a couple of years ago and it took a while to break them in, but now that I have…they are extremely comfortable and I can wear them all day. I do have a question though. I am 5’11 and I LOVE heels (I never wear anything less than 3 inches) but I sometimes wonder if it’s off-putting that I am so tall. I know there is nothing I can do (nor would do) to change my height, but how does my height affect shorter, male superiors? I recently interviewed with a substantially shorter male partner and heard through the grapevine that he had a Napoleon Complex and that my height would most likely intimidate him. Needless to say, I didn’t get the job.

    • Wear them! It’s really unfortunate if you didn’t get the job because of a petty man’s insecurities (which would be just as true if it was a woman), but you should own your height! My best friend is 6’1, and when she wears heels she comes across as incredibly confident. If you like wearing heels, you shouldn’t wear flats just to appease hypothetical or real insecurities in other people.

    • Wear them, but not for interviews :)

  20. yankee peach :

    I love Kate Spade, but I’ve never tried her shoes, but there is so much love for them here, I think I want to give it up and try a pair. Would anybody like to share how they run? I’ve got very boxy, small feet (6-6.5). Also does anyone have an opinion about Tory Burch shoes in terms of fit and comfort?

    • I love my Tory flats, and think they are a good value. However, just wanted to add that I also have a Tory tote and do not think it was a good value. (It’s canvas with synthetic, not leather, details, and cost $225.) I mention this, because since purchasing that tote I have been very cautious about Tory purchases based on a quality concern.

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