Work Shoes – Demystified


I mean, I guess work shoes aren’t all that mysterious, but I feel like they can be. Do I have to wear heels? What if I have foot problems? How do I manage the dirt of public transit without suffering the slings and arrows of ruined shoes?

Well, fear not, Fashion Fledglings, it’s time to talk shoes. Specifically, we’re going to talk about how to find cute, comfortable shoes for your standard business-casual office, even if you’re generally a flip-flops or sneakers kinda girl. Affordable, appropriate, comfortable, beneficial shoes do exist for people of all sizes and sensibilities, so let’s go over some basics and look at some links.

  1. To Heel or Not To Heel. Fashion mags and runway shows always have ladies in these spiky heels (SPOILER: it’s because the heels make the models stand and walk all sexy), and when you think of ‘dressing up,’ you picture heels. Even if you’re not a fan of them, you might have one pair stuck in the back of your closet, in case you ever need to ‘dress up.’ So how does a business casual dress code factor in? I say, wear heels to work only if they meet the Fashion Bird Acceptability Test in all four categories. That means that if they’re killing you by lunch time, they have failed the Comfortable part of the test and therefore they don’t get a pass. Don’t wear uncomfortable shoes to work, and the reasons are twofold: A) It’s bad for your health. Uncomfortable shoes can lead to stress injuries and chronic foot problems, and no shoe is worth that. B) Sitting around your office barefoot is SO unprofessional, and there’s really no way to explain how much ‘your shoes hurt but they were so adorable’ to your company president who swung by for a visit and found you with your shoes off. If you can’t wear those heels all damned day without pain, then skip ’em.
  2. Flip-flops? Maybe. This is a good time to read that HR-provided dress code, look at what your boss is wearing, and maybe ask if flip-flops are okay. I’ve worked in offices where ‘nice’ flip-flops – ones that are made of leather or embellished somehow – were completely fine, and I’ve also worked in offices where HR put an unequivocal kibosh on any shoes that go between your toes. Sometimes it’s a safety or health code issue, and sometimes it’s because a bunch of people showed up in dirty drug-store shower shoes because the dress code said sandals were acceptable, and those jerks ruined office footwear for everyone. If in doubt, wear more substantial shoes, but it never hurts to ask. The worst thing they can tell you is ‘no.’
  3. Travel Wisely. Taking the train to work for a couple of years absolutely murdered my poor shoes – running up and down rough concrete stairs, walking on dirty train floors, and dealing with the capricious Texas weather meant that my work shoes were wearing out far more quickly than my budget allowed for. I took a look around, and saw loads of ladies on the train wearing pencil skirts, silk blouses, blazer jackets…and running sneakers. They were obviously wearing their gym shoes while commuting, then changing into professional shoes when they got to the office. I started commuting in some crappy, torn-up ballet flats and keeping some nice shoes in my desk drawer at work. I’d change when I got there, and change back to crappy shoes when I left. If you’re not super into having different shoe options, one pair in a solid color that goes with all your outfits is a good way to achieve this, and them sitting in your desk outside work hours means they’ll last approximately forever, which frees up your dollars to buy more flip-flops for the weekend.
  4. If you Can’t Walk in them, Don’t Wear Them. Seriously though. Falling on your butt in front of your coworkers is embarrassing, but doing it in front of a client or executive will make you want to hide in your cubicle for the rest of the day. Don’t set yourself up for that. Buy shoes that you can walk in, quickly if needed, with confidence and without fear. Make sure you can take stairs and stand for a bit without wobbling. That mincing baby-giraffe walk that some women do when they’re unsteady in their heels is not the way to let your office know how tough, smart, and capable you are.

Professionalism Tip: If your company executives are coming through the building, if new clients or customers are showing up, or if you have a big meeting to attend that day, wear your nicer shoes. That’s the time to look polished, and switching from sandals to some low-heeled closed-toe wedges can elevate your look so that you feel – and everyone else feels – like you belong in that meeting, not like you’re the college-student intern who wandered in there by mistake. Dressing for the occasion says that you knew this was coming, and you put effort into preparing to be there. That goes a long way reputation-wise.

So you hate heels, can’t walk in them, not gonna do it – what’s a Fledgling to do when she wants to look like she’s at work to get stuff done? Let’s go to the internet for some examples.

  • Ballet flats – the BEST go-to work shoes, in my opinion. Flat, comfy, cheap, available in tons of colors and decorations or just plain black. You cannot go wrong here.
  • Low wedges – absolutely wonderful for looking juuuuust a lil’ bit fancy, but not having to toddle around in tall heels all day. I find they even help my foot pain if my heels are achey. Bonus: a lot of times higher wedges are easier to walk in than shoes with a thinner heel (think stilettos), so if you want to add height, a wedge might work better for you in the being-able-to-walk department.
  • Boots – we all need a good pair of boots, whether for bad weather, or just to feel cozy during pumpkin spice season. Some low-heeled, neutral-colored boots will pair great under a dress, slacks, with leggings, without…you got options with boots.
  • Dress sandals – okay, so the jerks in shower shoes made work say ‘no flip-flops,’ and where do we go from here? there are plenty of dressy sandals out there, from earthy to blingy, so take your pick of the comfy options, get/give yourself a pedicure (gnarly toenails are not impressing anyone), and get to work! Summer doesn’t have to mean sweaty feet if you have good sandals.

‘Why are you putting all these non-discount shoe brands in your links?’ I can hear you asking. So far I’ve given links to more discounted stores, so I get it. The main reason is this: You get what you pay for with shoes. Moreso than any other article of clothing, the money you put into your shoes will come back to you in longevity and comfort, and when we’re talking about your foot and back health, that’s worth an investment. If you hate shoe shopping, a really good-quality pair that goes with all your work clothes is all you need, and if you invest in that quality, you won’t have to go shoe shopping until those guys fall apart, which will take a lot longer than the $8 Old Navy ballet flats. I’m not telling you to skip those cheap ballet flats, but I am saying you get what you pay for, and they will wear out after a few months of regular use, which will bring you right back to the shoe store to spend more money and replace them. Do yourself a favor, if you can, and go for a higher-end brand of shoes, especially if you suffer from foot pain or have any medical issues that cause foot problems. You’ll be thanking yourself after a day of running errands when your feet don’t feel like they’re going to fall off.

Alright, here’s my last note on shoes for this week: If you have a medical condition that a doctor has diagnosed (this includes pregnancy), and the only shoes you can wear are non-work-approved, talk to your HR rep and get their sign-off to wear the shoes that accommodate your condition the best. It’s a small thing to allow, and most companies are perfectly okay with it. Don’t suffer for the dress code if you don’t have to, and definitely don’t ignore your doctor’s orders for the sake of the dress code. Not at all worth it when a company is legally required to work with you if you have a medical issue but can still do your job.

Happy shoe shopping, Fashion Fledglings! Next week we’ll talk about bags and purses, and how to go from college student to professional grownup just by getting a new bag.


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