
You probably could have guessed that I have a deep fondness for shoes, especially after posting about feel good shoes in the past. Today I’m sharing some thoughts on shoes—buying them, wearing them, and more.
On knowing your foot type. I have strange feet—wide for a woman, though between B and W, with high arches. (Unfortunately, this makes flats pretty uncomfortable for me. I still wear them—which is probably stupid of me—because heels can be cumbersome and slow. I also don’t have the endurance to go more than a half mile in them usually.) But it’s important to figure out what’s comfortable for you, and find the right fit. Thankfully, with the Internet, you can find reviews for just about everything under the sun.
On picking the right soles. You’ll get maximum use, breathability, and comfort out of genuine leather than you will out of faux leather or other types of materials. You’ll also find yourself with fewer blisters and calluses. About two years ago, I committed to buying only shoes with genuine leather soles. It means you might spend a little more—like $155 for Ann Taylor perfect pumps instead of $80 for ALDO pumps—but you’ll notice a difference in how your feet feel.
On finding shoes you like. Maybe you’re into wedges, which are more supportive. Or maybe you like sky-high stilettos with a platform. You might like feeling the ground firmly below your feet with flats. Trying shoes on, buying selectively, and wearing them with confidence are all part of finding shoes you really like. And once you do find that pair, buy two pairs because these will probably be the shoes you wear the most.
On wearing heels. Even if you have a self-professed hatred of heels, you will find that every now and again you will have to wear them, so start looking for a pair that works for you. Start with lower heel heights and kitten heels. (Personally I found that for me, 3.5″ heels are my max; I get that perfect mix of height, balance, and comfort. Anything higher and I think my center of gravity goes out of control. My favorite pairs of heels: Ann Taylor perfect leather pumps and kate spade Karolina pumps.) Check out veteran heel-wearer Tiffany’s tips on walking in high heels for getting started.
I stumbled upon a book at the library called Women from the Ankle Down: The Story of Shoes and How They Define Us, which is great so far. If you decide to pick it up, let me know what you think!
So tell me: what kind of shoes do you wear? Do you like heels, or do you find them uncomfortable? Feel free to ask questions or show me what you wear in the comments!










I had foot surgery six years ago, so I can’t wear heels at all — it puts too much pressure on that area. It’s probably for the best anyway considering I’m constantly tripping and running into things, so it would just be added risk. So I live in flats!
Is there some kind of insert you could wear with flats to make them more comfortable?
I’ve found a couple of flats with good arch support, but my issue is toe box. :( Still working on finding some more. (I actually own the black pair in the collage, which are great.)
I totally agree with you that leather shoes are the way to go! I absolutely love the AT perfect pumps! I had no idea Kate Spade made shoes. Have you tried those before? I really need a nude pair of leather pumps, but Ann Taylor doesn’t really offer them at the moment!
I own two pairs of the kate spade Karolina pumps (the ones I linked to) and would highly recommend them. They’re the most comfortable heels I own!
I wear mostly flats since I work from home and when I’m not, I am running all over the city and hiking up hills. But when I go to tradeshows or to the main office, I usually wear Cole Haan Air Talia Mid pumps. They’re 2.5″ and that’s about all I can handle if it’s not a wedge. I own them in black, grey suede, and chocolate suede. The trouble is, I can hardly find them anymore. I hope they’re not discontinuing the style. They were a stretch for my budget at the time I purchased, I wish I had been able to stock a couple of extra pairs in the closet! I’ll have to try the Karolinas.
OK, San Francisco seriously looks like the hilliest place on earth. (Still have no idea how houses manage to be on a 45º incline! Killer engineering, maybe.) I’ve heard a lot of great things about the Cole Haan Air series, and those look very comfortable. I think Zappos still has them!
The Karolina pumps are great overall, and I’ve never slipped or had issues with them. They’re expensive, but I think a classic color will last for years to come.
it seems that we have the same feet! i find that i am a great swimmer as a result of the wide foot, but they are disastrous in terms of finding shoes. i also swear by the ann taylor perfect pumps, and the patent peep-toe slingbacks that are currently on sale is my new favorite pair – great neutral color, and very comfy! haven’t tried the kate spade karolinas, so thank you for that tip!
i have one pair of old cole haan ballet flats that i wear constantly (i work in the bronx zoo, so walking a lot is essential!) and they fit my toe box perfectly, the leather is super soft, and the nike air cushion makes them better for longer use.
I’ve never really gotten on board with slingbacks, but if you say the Ann Taylor ones are great, I don’t doubt it. I’ll have to give them a try! And Cole Haan seems to be getting a lot of love from this post—looks like I will have to try something from the Air series.
I am a long time heel wearer, and but have a hard time wearing pumps. At first I said, maybe I have weird feet, and accepted that pumps are not for me. But in recent months, I refuse to accept that there is something wrong with me, and that I was born this way, and maybe there are other people who are just struggling (with pumps) just like me. Perhaps I am listening to too much Lady Gaga? :) I have been searching near and far and researching as much as I can (even at work sometimes.. opps!) online for a good (comfortable, classic style) pair of pumps for work and play. I’m going out on a whim… I am listening to a COMPLETE stranger online about these Karoline Kate Spade shoes and have ordered it on ebay. I even found a coral pink color, very similar color (if not the same) as your Feel Good Shoes. Just want to say… it’s all you… :) Whether it’s bad or good… it’s your fault. haha It’ll come in the mail by next Tuesday it says.. Wish me luck! And… Thank you. Happy Thanksgiving.
PS: Ann Taylor’s Perfect were my first choice, but they do not have my size right now! Ugh!!!! And they even have the 40% off discount going on right now too!!!! :*(
Happy Thanksgiving to you too, Kim! So glad you stopped by, and my fingers are crossed for you that the Karolinas work out for you – they’re still my favorite and most-worn shoe style in my wardrobe. (I also think they fit more true to size than the Ann Taylor pumps!) Be sure to stop by after you get them and let me know what you think. :)