Dressing for Work:  Part Three of a Five-Part Series – Shoe Porn

Yup, shoe porn is a thing. I wish I wasn’t addicted, but I am. I have a Pinterest board solely dedicated to Guilty Shoe Pleasures. Like a lot of women (and men), I love shoes. I’ve learned a few things over the years about buying and selecting the right work shoes when dressing as the boss.

Last time, in Part Two – Confidence in Fit & Comfort, we touched on the subject of work shoes briefly when we discussed feet and exposed skin in the workplace. Feet, especially toes, seem to make some people uncomfortable for different reasons.

Be sure to check out the rest of the Part Two detailing what body parts to keep under wraps if you want to dress like a boss and the second question I ask myself each time I dress for work. And ICYMI and want to start from the beginning, here’s Part One.

Today we’re going to talk about shoes and the third question I ask myself:

#3. Do these work shoes read, “I’m the boss?”

When selecting shoes for work, there are so many things women have to take into account:

Weather, walking distance, stairs, parking lots, grass, time on feet, speed, style, culture, carrying heavy items, uneven surfaces, dirt/gravel, snow, rain, condition of feet, socks, color, hemline, pants, injuries, ankles, dressiness, professionalism, etc.

On top of all those factors, when you’re the boss, you really want your shoes to reflect that fact. Orthopedics aside, your shoes matter as much as the rest of your outfit. And can make or break your overall look.

For me personally, it goes back to power and strength again. If I have a cute shoe that works, one that covers all the basic needs according to those factors above, it still might not be enough for me. If it just “works” but doesn’t “finish” the look or “Dot The I” per se, then it’s not accomplishing what I really want. I want my shoes to perfectly complete my look, be the cherry on top and match my position of authority.

I’m going to share a few things I’ve learned and what works for me; just keep in mind I’m super picky, have had foot injuries and expect to be comfortable most if not all of the time – so I’m hard to please in this area!


    • I like to have most of my foot covered. (See Part Two for more on EXPOSED SKIN). Peep toes are one of my favorites. I also love pointed toe slingbacks. I struggle with regular pumps since my heels are narrow, they just slide off all the time. So slingbacks are my go-to instead of pumps.
    • I love a kitten heel with a pointed toe. I’ll go up to a 3” heel for work. A block heel is also “powerful” to me. A tasteful platform will sometimes work, but not usually – they seem to read sexy and/or casual to me. Four inch heels are maximum and only for special occasions, not everyday boss lady stuff.
    • I prefer a heel over a flat slipper shoe. The heel reads more “adult” and “serious” to me. I know this seems ridiculous and so specific, but I’ve changed out of flats so many times it’s shocking I even try them on with a work outfit anymore. Don’t judge me! I’m just sharing my thought process honestly with you 😉
    • I love my brogues (or oxfords – gosh I didn’t know the difference between them until just now) and my dress loafers – these help me balance out the girliness. With my long hair, feminine shape and soft voice, I can wear menswear like there’s no tomorrow. Unlike when I was 10-11 years old, hard to mistake me for a dude these days. I love love love the androgynous looks and designs today. But mostly I enjoy mixing tomboy with classic and edgy pieces for my own personal style.
    • I prefer a pointed toe or squared toe versus a rounded toe, but I’ll still wear a rounded toe here and there. I think that goes back to my “soft” vs “strong” balancing act – where a rounded toe seems softer to me than the others and I’m looking for strength to balance out my natural softness.
    • I don’t wear wedges to work. They feel too casual for me, but most of mine are made with more casual materials like canvas and cork. Most of the wedges that would “qualify” for a professional atmosphere look too “little girl” and don’t read “I’m the boss” to me. What do you think, agree or disagree? Do you have a great wedge for work – post your pictures in the comments!
    • I love boots of all kinds as long as they fit the circumstance. Even over-the-knee boots work, but only with pants, leggings, tights and/or under longer skirts (absolutely no skin showing). I wouldn’t wear work boots to an office setting (the boots you muddy up riding horses, hiking or other outdoor activities). Dress boots and booties rock.
    • No flip flops or flat sandals that show toes. And I don’t like a flat platform for work either. Gosh I’m picky.
    • I do wear sneakers now though! High quality, clean sneakers and tennis shoes with office-like athleisure-wear when it’s appropriate. I don’t wear the same sneakers to work that I wear to workout in. And I like to wear socks or “invisible” footies with my sneakers.
    • I have a pair of white leather slides with a block-ish kitten heel that show my toes a little…I’ve worn these to work before. I call them my “granny shoes.” They cover a good portion of my foot even though they’re technically open toe slides.
    • What have I missed? Share your favorite work shoes in the comments below!


    • Always shop for quality materials and finishings. I can usually tell a well made heel from the sole…it has one piece of leather all the way from heel to toe. Believe it, quality materials are almost always more comfortable!
    • Take your brand new heels to get the bottom of the toe reinforced before you even wear them.
    • I don’t buy strappy shoes for work. Too many thin straps, strings or ties seems to give off the sexy vibe a little too much for me.
    • Make sure the shoes you buy are immediately comfortable when trying them on. They will not get more comfortable over time unless they are more than $300 and made of Italian leather.
    • I like to buy dressier, less casual materials for my work shoes. Leather and patent leather are better than cork and canvas. This can work opposite too though…if I’m buying a very dressy shoe style, it might look cool with canvas and vice versa.
    • Ask about the return policy. You may wear them a whole day and not ever wear them again because they hurt so much or just didn’t fit your foot as well as you thought when you initially bought them.


    • I always have a pair of flip flops in the car for emergencies like that time I had to park uptown in a gravel parking lot and walk a mile to the office for my meeting.
    • I always keep a pair of sneakers at the office.
    • I sometimes use this no-friction bandaid stuff on my heels and edges of my feet with a new pair or a pair I know will rub me the wrong way.
    • I use these sticky heel grip inserts with pumps. They help a little.
    • I’ve tried all kinds of different ball-of-foot pads for heels. They don’t work for me at all and sometimes just make the toes too tight.
    • I heard if you tape your 3rd and 4th toe together, it can help with ball-of-foot pain, but I haven’t tried it yet.
    • I superglue Superfeet inserts into every shoe and heel that will allow them!
    • If you can wear silky footies in your heels, it helps.  
    • Don’t wear the same shoe or exact high heel height two days in a row. My feet die in this scenario.
    • Schedule higher or tighter heels for desk days.

This past year I tore a tendon in my foot. It gets inflamed and I can’t wear anything but Superfeet shoes or my hiking boots on those days between periods of icing it. Pretty sad and disappointing for the time being. But this will NOT keep me off the wagon for long. Is there an addiction hotline for shoe porn?

So, what do you think? Where are your favorite places to buy work shoes or your favorite brands? Do you have any resources, links or ideas to contribute? Remember, I’m not a trained fashionista or stylist or anything…just a girl who loves shoes and has a sh*t ton of dressing for work experience to sharework shoes.

Those are my white granny slides in the picture…the most foot I’ll expose during regular business hours.

Also, stay tuned for the next article in our Dressing for Work:  Dress Like A Boss series. Learn the fourth question I ask myself each day I get dressed for work and how it helps me be a better communicator.

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