Stylish Work Sneakers For Women (And Advice On What Should Women Wear While Canvassing)

stylish work sneakers -- and advice on what should women wear while canvassingWe recently got this question from a reader who’s running for judge (woot, you go!), and it raises an interesting issue of what is casual but professional footwear for women — for weekends and other outings outside the office. Can you be professional in sneakers? What are some other options besides work sneakers? In a bigger sense, what should women wear while canvassing or otherwise politicking for office? We tried to talk about the casual-but-professional-uniform a few years ago, but I still feel like it’s an issue. Reader K asks:

Kat, I am a 42-year-old lawyer, mother of two, and am running for judge [locale redacted, but suffice it to say somewhere hot]. I made it through the primary and am in a runoff on May 24. There are occasions (like when I’m working the polls) that I wear my campaign t-shirt and a pair of jeans. I have worn boots with my jeans (in February), but now that it’s getting warmer, I think I need a pair of sneakers. The problem is I have running shoes, boots, flip flops, or dress shoes. Do you have any suggestions for stylish, comfy sneakers?

Congratulations, and good luck!  As to the question about what women should wear while canvassing: very interesting.  Comfortable, stylish, but vaguely professional sneakers: I’m curious to see what readers say here. I’m a diehard Chucks girl myself — they’re classics! But aside from off-white Converse, I would worry that they show a bit too much personality — I associate black ones as being an outsider/artist/comedian kind of shoe, for some reason, and colorful ones being too young/wacky. (I currently wear gray ones on weekends, which perhaps is my way of saying “I used to feel like an outsider but now I’m a mom and have no feelings of my own.”) Instead, I might steer you toward a few other options for work sneakers and other casual-but-stylish shoes:

What should women wear while canvassing or otherwise campaigning for office? More women than ever are running for office, but striking the right mix of "professional but relatable" is, as always, difficult. One reader who was running for judge wrote in wondering specifically what shoes she should wear while canvassing in hot weather. (Hooray for women in politics! Go go ladies!)

What Shoes to Wear While Canvassing

First, the sneaker/oxford type of look: I’d go for the Onitsuka Tiger, which is hugely popular both on Zappos and among readers here — it has a low profile, a zillion color combos to choose from, and fits the bill of a comfortable shoe and work sneaker. The second option: Cole Haan’s OS Grand, which is extraordinarily lightweight and comes in sneaker-y versions as well as more oxford-y versions. The plus side of having a more business-style oxford is that you can wear it with cropped pants, whether they’re khakis or denim. If you’re daring enough to try canvassing or just standing for an extended time in a heel, consider another Cole Haan staple, also ridiculously lightweight: the Tali. (It used to be part of their collaboration with Nike Air — on my last visit to a Cole Haan store the SoHo salesmen confirmed that it’s still one of their best sellers.)

Second, I feel like the high wedge/espadrille heel is a very Kate Middleton-walking-a-lot-outside look — there are some cute options from Seychelles, Clarks, or these highly rated Toni Pons now; SperryLoftFree People also have some cute espadrille flats. (Flashback time: Years ago people used to sing the praises of Kate Spade wedges for this very purpose.) I don’t really think it matters for these purposes if your toes are exposed, but know your demographic. (I would also note that if making the time for a pedicure or plain, well groomed toe nails isn’t high on your priority list, I’d stick with a closed toe shoe.)

Finally: of course you can wear ballet flats if those are comfortable for you for walking (they wouldn’t be for me, but that’s me!) — people swear by the comfort of AGLs. There are sportier versions of this look as well, such as Crocs’ ballet flats or these Lands’ End bungee ballet flats (recommended by readers just this past weekend!).

General Advice on What Women Should Wear While Canvassing

As for what else to wear: I still think a dark rinse denim looks best. I used to think I was dating myself by preferring bootcuts over skinnies, but the crazy thing about trends moving so fast is that I think anything goes at this point. I think skinny jeans are the elder statesmen of the bunch, while bootcuts are “back,” flares are in, and there are a zillion different cropped styles (boyfriend, skinny, flared, flared crops!) that everyone is still getting used to. I believe it’s important to stay up to trend on your denim style, but for this particular purpose I’d stick with an established look — to me this means full-length boots or flares, in a dark blue rinse with as little distressing as possible. If you’d rather go with skinnies instead, I might steer you towards ankle boots — with just a touch of ankle showing, which is certainly fine through May. The Sam Edelman Petty is still going strong for a flat option; check out our most recent roundup for other booties. If you worry about overheating, you may want to look into some of the trendy cut-out booties, such as these perforated ones from Jeffrey Campbell or these highly rated $79 Rebels booties. I always like a blazer with jeans, even if there’s a campaign tee beneath it (ooh, or have you considered having a custom scarf made with your campaign logo on it? Might look great worn long and loose with the blazer, or wrapped once around your neck).

Ladies, what are your thoughts on what women should wear while canvassing? Perhaps more importantly, what would you expect a future judge to wear on the campaign trail(or to not wear)? Any super comfortable flats, sneakers, or summerish boots to share? 

Pictured, clockwise: Cole Haan OS Grand, Onutsuka Tiger, Sam Edelman Petty, AGL ballet flat, Lands’ End bungee ballet flat, and the Cole Haan Tali

What ARE the best comfortable, casual, professional shoes to wear if you're on your feet all day doing something career-related like canvassing? A reader who was running for judge wrote in for advice...


  1. I am a big fan of casual shoes at work. I am currently an intern at a publishing house, so wearing flats is a must, since I am literally on my feet all day. There are times I wish I had more support, but wearing running shoes is out of the question. What do others who must be on the move all day wear?

    • Anonymous :

      I think you need to invest in really good flats that have the support and comfort of a sneaker. Cole Haan and Geox are good brands.

    • Flats with arch support. My personal favorites are LL Bean skimmers. In the winter, Dansko makes adorable ankle booties (although last season was pretty frumpy), but those are a serious investment (although well worth it in my opinion).

      • I just did a post on flats with arch support, actually! On the off chance that it’ll help someone here.

        • I clicked over to this blog, and wanted to say that it’s great. Well written, informative, and interesting topics. You’ve got a new reader in me!

          • Aww, thanks for the compliment, anon! I’m glad you find it informative and interesting. I started the blog largely because I wanted to make it easier for other people to find things I’d found hours researching.

        • Anonymous :

          Another new reader here. Great blog!

    • Anonymous :

      Cole Hand ZeroGrand oxfords. They are basically sneakers.

      • I use arch support inserts in all my shoes, flats and heels. Makes a huge difference!

  2. workingmomz :

    Good luck reader K!!!!!

  3. Anonymous :

    I put a pair of Superfeet black insoles in a pair of nothing special Banana Republic ballet flats and the support is GREAT for walking.

  4. Anonymous :

    Sketchers Go Walks are the best slip-on sneakers. They are insanely comfortable. Some styles are a little more athletic/utilitarian looking, some are a little more stylish.

    • I just bought a pair of Asics MetroLyte slip-ons, and they are so comfortable and received so many compliments that I bought a second pair to keep at the office for lunchtime walks.

    • Philanthropy Girl :

      +1 to Sketchers Go Walks. I am notoriously hard on my shoes, but have found them comfortable, stylish and durable.

  5. I just bought the Cole Haan Pinch Weekender loafers in fuchsia leather (impulse buy while walking through Nordstrom on my way to another store), and I love them. I don’t see them online at Nordstrom in that color, but Zappos has them for $100 in more sedate colors as well as the pink. I’ve worn them out on weekends either to accent pink in my office or with jeans and a navy or black top and gotten tons of compliments. My sister says they are old lady shoes and I may have matched a two-year-old at dinner, but they make me happy.

  6. I like my all black Vans. They are comfortable and look cute with either bootcut pants (as long as they don’t drag) and with ankle length skinnies.

  7. I have a pair of basic black TOMS for just this. They go with everything, and are super comfortable. They don’t provide a great deal of arch support if you need anything like that, however.

  8. I just bought a pair of the new Chuck Taylor IIs (in grey) and I absolutely love them. That memory foam insole…. so good.

    • omg this is huge thanks for posting! I love my Chuck Taylors and I prefer them to unsupportive ballet flats if im going casual but Chucks with memory foam.. I need these.

  9. If you want to look (quasi, ertzatz) professional in sneaker, I recommend all-white. K-Swiss, Adidas, even Keds.

  10. What are the thoughts on this shoe?

    • Anonymous :

      I like them.

    • I just bought them. I do not need new sneakers. So that is what I think of them.

    • I own these in white. Bought them after getting blisters walking everywhere in Chicago on a trip. They are cute and dos the job.

  11. Try some Vionic by Orthaheel shoes. OMG so comfortable! I can’t wear regular flats. They essentially gave me plantar fasciitis from too much running around in nonsupportive ballet slippers.

    • I’ve been meaning to give them a try! How are Vionic shoes’ uppers, though? I’ve heard they’re kind of cheap and uncomfortable.

      • I have some Vionic (brown ballet flats) I bought at Sierra Trading Post. Leather but faux croc upper. Very comfortable but after only 6M wear, very scratched up, finish rubbing off. Need to see if polish will help or not. I fear not. Very sad!

  12. Supergas, Tom’s, or Vans would work for this.

  13. these are REALLY expensive for a sneaker, but so comfortable.

  14. Anonymous :

    You can never go wrong with the classic black and white checkered vans. With skinny jeans and a black (or colord) tunic top, it’s a perfect combo.

  15. Anonymous :

    I wore Dansk clogs while canvassing for office. Stability and padding were good. They have some perforated styles that might work for summer.

    ordered these in nude and black and they’re amazing. i see that others have caught on because nordstrom is running out of them. Stan Smith’s are really popular right now but theyre so neutral and go with anything

  17. Black keds. Simple, timeless, and available on amazon prime.

  18. Former Female Candidate :

    I’m a former political candidate who ran in the spring, and I disagree about routinely wearing jeans (unless you know you’re headed to a casual event where jeans might be a tad more formal than the other guests). When knocking doors, you need to look professional. No shorts, no jeans (unless they are black and look like dress pants). I always wore biz cas, even if with sneakers. (I did usually wear the Tiger sneakers, which I already owned, if I had to wear sneakers.) I also wore ballet flats often. Just prepare to have tired feet. Find a hot tub (if you ever get the time).

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