A Walk In 7 Shoes: What I Learned From 7 Days Of 7 Pairs Of Fabulous Footwear

Every morning, I reach for the same pair of shoes. Almost without fail, I slip on a trusted shoe-of-the-season: In the winter, it's usually a pair of black booties; in the spring, probably a cute wedge; for the summer, a strappy sandal; and in the fall, booties again. What's more, regardless of the season, all the shoes have a similar look and feel: Most are black or brown and each has some sort of heel to lift me above my 5'1" frame.

So this week, I decided to switch it up. For seven days straight, I forced myself to actually wear the different shoes in my closet as opposed to simply resorting to the same pair. Now, I don't have that many shoes, but I do understand that I am lucky enough to own even just one pair, let alone enough to last me an entire week without repetition. For this, and the more selfish reason of just wanting to up my wardrobe game, I planned to give this experiment a go. I mean, how many of us have a pair (or two) of shoes worn once, only to have them immediately overtaken by a possibly tamer, certainly more comfortable default?


I embark on this journey in a frigid New York City with a great deal of trepidation. When it's cold, it's easy to just slip on my booties and call it a day. But no, I've committed. I'm doing this. Who cares if it's not going above 20-degrees Fahrenheit today? I can do this. I CAN do this.

Since I'm not back at work yet, today proved a bit easier than expected. I decided I'd head out for a day at the Brooklyn Museum, as it isn't too far from my house — a walkable distance if the weather is relatively pleasant and, of course, if I have the appropriate footwear. Due to a decent snowfall and some freezing rain a few days before, this meant Bean Boots.

A stalwart of the LL Bean brand for years, I — like many others of my generation — only just recently discovered the leather-top, rubber-bottom, lace-up Bean Boots when the Polar Vortex of 2014 meant snow every other day and subsequent patches of black ice and deep pools of slush. I never really like snow boots, always too heavy and/or too tall for my admittedly short legs. But Bean Boots changed the game. Lightweight, but perfectly insulated with a cozy sock and falling at just the perfect height, my Bean Boots take the top spot when it comes to my winter wardrobe favorites.

So, my walk and entire day spent in Bean Boots was an expectedly good one. I felt comfortable and confident, especially because I knew that the chances of me falling on my face were slim to none.


Another freezing cold day in New York City. As with most Saturdays in the wintertime (and most times, to be honest), I spent the majority of 10th holed-up in my apartment watching Netflix, so no shoes were needed. By 9:00, however, I needed to get dressed and head out for a night celebrating my and my good friend's birthday.

Now, having a winter birthday means that I have grown accustomed to ruining outfits by wearing a jacket all night, to messing up a blow out with a beanie or earmuffs. Living in a city, I've also now begrudgingly accepted the idea that I have to walk in the cold to wherever the celebration destination may be. Up until the 10th, I let the weather dictate my footwear — but not this time.

For my 2014 birthday, I decided to wear the fancy designer heels that my mother gave me when I graduated college. Since May, they've been sitting in my closet unworn, subsequently plaguing me with guilt. So just slipping them on, I immediately felt a bit better, at least psychologically. Of course, the shoes were beautiful, adding just the right amount of celebratory look-at-me-it's-my-birthday sparkle; plus, for all the heel, they were surprisingly comfortable.

That being said, I probably won't be wearing the shoes again anytime soon. Precisely because they were a perfect "birthday shoe," these heels will be tucked away in my closet until the next occasion where I'd allow myself to take an Uber instead of the subway.


Ah, Sunday, brunch-day. After spending the night out, my Sunday proved pretty easy-going, but I wanted to keep this experiment strong, so I went with another pair of shoes that have barely seen the light of day: All-over bright pink Converse.

I'm always wanted to be someone who wore Converse on the regular, but I never feel that I could really pull them off and any pair I wore always seemed to give me blisters. Yet, I keep going back hoping things have changed and as this Sunday proved, I guess things maybe have.

Of all the shoes I wore throughout the seven days, these shoes garnered the most compliments. I'm sure a lot of that had to do with environment — waiting to eat and eating brunch at a cafe serves as a rife environment for casual conversation, at least much more so than the office — but I'm going to consider the 11th a Converse victory nonetheless. Not only were the shoes casual and comfortable, but more so than the run-of-the-mill design, their unique style (and platform) fit better into my style and made the whole day a bit more fun.


On day four the true test came: I would have to commute to and from work, plus, you know, actually work in whichever shoes I chose to wear. Easing myself in, I chose to go with a pair of fancy flats I normally reserve for warmer weather, making the experiment more about whether or not I could successfully transition shoes from one season to another.

For some, this surely proves an easy task, but as has already been made extremely clear, I remain entirely inept when it comes to winter footwear. Perhaps it's some sort of post-traumatic stress from the winter days in high school when I would wear flats without any sort of sock, essentially walking around barefoot in below-zero temperatures, but I'm so afraid to wear shoes with any sort of over-the-foot opening from November until March, fearing my feet will freeze off over the course of the day.

As any sane person would guess, however, such was not the case on Monday. Even when wearing thick tights, my feet still can't stay warm in the winter if I'm wearing a standard flat, but when I wear slipper-esque flats like those pictured above, with a bit more structure and insulation, my feet do just fine.


The time has come to wear heels. Like many women, I keep a pair of heels beneath my desk in the office, but I never wear them on the commute there and back. In an act of solidarity with all those women who somehow manage to get to work wearing heels, I walked out the door with my heels on an never looked back — but boy, did I want to.

Not even a minute in, and I could feel exactly where my feet would throb for the rest of day. Moreover, while I don't usually consider walking in heels difficult, traversing sidewalks in dire need of resurfacing and climbing up and down crowed subway staircases didn't exactly help matters.

In the few random moments I forgot about the pain, I did, however, feel a bit fancier, a bit more powerful — working in a casual office, I sometimes forget the empowering spell heels cast upon self-confidence, as I don't ever feel the need to wear them. But as much as I loved those moments, I don't think I'll ever really wear heels to-and-from a place of work ever again, unless, of course, I have the ability get a car to take me there.


After putting my feet through absolute torture, I decided to give sneakers another go. I've always been keen to Vans, having more success with them than any other casual shoe. This pair goes perfectly with a favorite outfit, their galaxy print adding an unexpectedly kitschy touch. Like the Bean Boots before them, I knew these shoes would not give me any problems in the comfort department, particularly in comparison to the day before. What I wasn't counting on, however, was the change in confidence from one day to the next; wear a pair of Vans after wearing a pair of heels and you'll feel the difference.

Certainly, such a feeling is subjective and again, it's not all bad — having the ability to walk definitely helped my overall happiness. Yet, there's something to be said about heels over cool sneakers or even fancy flats. Heels just make me feel more professional, more powerful. Some women can absolutely pull off shoes like these and make it work, but as I discovered on the 14th — feeling shorter than ever before — I am not one of them.


And on the last day, back to boots. These are not my usual go-to booties, but they are admittedly quite similar. More often then not, I go for things much more basic than these studded, pointed toe boots, however such tendency toward simplicity is a common critique I receive from friends and of course, my mother. They say I need to add more to my wardrobe, and these shoes were my attempt, a compromise between their "more" and my "less."

Overall, I really liked the day I spent in these boots. They were warm, they garnered me a few compliments, and I really did love what they added to my outfit. I will say, though, that they were not among the most comfortable boots — they seem like the type that needs some wearing in. But that shouldn't be a problem, because I think I'm going to start wearing them (and a few others) a lot more often.

Images: Melissa L. Haney