In the past, my shoe closet was always fraught with emotion. A literal spewing of myriad desires and whims. It’s peculiar how this category is one where the most stylistically balanced amongst us can lose their shit. This unguided indulgence of mine came at a cost - physically and mentally. Physical in the sense that I had no business wasting so much on pieces that never made their way to the light of day. Or that worse, when they did, sent a bizarrely confusing message about who I am as a person. My chaotic choice of shoes sent vibes that left me feeling “incredibly uptight”, “fussy”, or just flat out “dull and basic”.

But here I am today - three years under my belt now of analyzing my style, thinking about my actions emotionally and analytically, and how I can better articulate the why behind what I, what we, choose to wear. I smile when people thank me for the unselfishness I exhibit when imparting all of this style knowledge because, at the end of the day, it’s helped me personally - so much. Once I distilled what I buy into three categories, the Without Fails, the In & Outs and the Had to Haves, (chapter in book here) it allowed me to step back and really look at my choices objectively. I had created a system for evaluating what consistently works for me as a Creative Pragmatist. Like most of you, I’m someone who really really thrives when fully understanding my personal style. It became clear that for me too stop leaning in to every whim of a trend, I had to first understand how to describe my personal style (chill, modern and classic) and second, recognize what items would help me show that visually. In every facet of my life, not just when I’m on vacation or at a special event. The three categories needed to look like a pyramid - turn it upside down and you see it resembles a spinning top. And that’s how you feel when your Had To Haves become the biggest player in your closet

I quickly realized my clothing was fairly balanced - especially in the Had to Have category - I was able to exhibit control. But shoes? It wasn’t just a spinning top but a full on tornado. Every luxury name, the most important trends of the season, and sometimes in sizes that had no relationship with my actual foot. Why was this so out of hand? Through this unpacking of my style thoughts, I realized that with no real measurement for how to identify when a shoe would be the shoe I would actually wear, I was just simply working off of emotion. Did it tug at me? Goosebumps? Yes? Done. Sold.

When I started researching the wear vs. investment of my purchases, the shoe that really made me pause and think was this one here, from Celine, I bought nearly ten years ago:

At the time, I thought I was buying into a trend. I scolded myself as I handed over my Amex card, thinking, wtf am I basically buying a designer trendy riff on a Birkenstock. But I wore them out of the store. And then I wore them a ton. Not because of comfort ….. though they were. But they oddly seemed to go with everything I owned. A pair of skinny trousers? They made them cooler. A dress? It took it down a notch. Suddenly I found myself wearing skirts I’d owned and rarely worn - because they seemed too fussy with a heel and too feminine with some of the blingy sandals in my closet.

At the time, I couldn’t put the words to why I was wearing them a lot. I thought I had “good luck” buying the right shoe trend and didn’t have a road map for how to recreate that success. Now I do.

The Celine shoe was the epitome of unfussy: a strong black faille upper, a strange shape, the dark burgundy rigid footbed. That’s it. I realized that most shoes like this have a contrast colored sole that’s distracting to the eye and making outfits feel less sophisticated, messy even. Go look in your closet - if you bought a shoe you thought you would wear a ton, but the sole is a contrast color to the upper - I bet you don’t wear it anywhere near as much as you’d hoped. It’s why when I buy a Birkenstock, I choose the Arizona style that is all one solid color. Quiet - but a statement at the same time.

Know this - I’m not saying you should never buy a shoe with wildly contrasting colors. I’m just helping you set your expectations on how much wear you will get out of them. Ok?

Approaching my shoes in the same way I do my clothing, I’ve been able to distill the commonalities in the ones I will live in (my WOFs) , the shoes I’ll wear a little and try to not regret having dipped in to the trend (my in & outs) and the ones that I’ll appreciate but rarely every put on my feet (my had to haves). And if I’m smart (which I am, now, I promise) I will have just a few of these HtH’s in my closet as I’ve learned the difference between love and lust. Love is real and stays around for the long haul.

The WOF shoe checklist:

I'll give you an example of an ultimate WOF for me:

I’ll break it down for you - show you how this one shoe hits on all these elements - for me. Now remember, all this utility without the visceral love is no good. You do need to love the shoe you’re buying - this isn’t a pack of batteries here that simply serve a function. But LOVE coupled with the ultimate in PRAGMATISM = a ton of wear. Every time. See? I’ll break it down for you how this one hits on all these elements - for me. Now remember, all this utility without visceral love is no good. You need to love the shoe you’re buying - this isn’t a pack of batteries here that simply serve a function. But LOVE coupled with unbridled PRAGMATISM = a ton of wear. Every time. See?

The shoe layers up for a lot of months (a,b). The neutral color adds depth to an outfit (b) - this outfit would have been just fine with a black sandal. Fine. But a good strange neutral makes it….more. The shoes are clearly made for walking. That’s obvious. But an eased shoe like this, worn for evening (c) makes you feel like you’re in on a secret. Slightly smugly chic. You don’t need to brag, but it’s good. These shoes give the nice slim to something big (a) or the nice skin when your look has a lot of coverage (c). All the marks in one shoe. Plus the love. All good.

Shoes can surprise you, in their functionality. Employing them for the technique of one/ton/none, or the good irony and friction is a form of functionality. Thinking of them as tools will allow you to know when to employ them to build the vibe you’re hoping to give.

A simple slide in a leather that’s brushed to give interest without taking all the attention. With all denim, the navy shoe gives really good “one.” I love a navy shoe - I find it far more interesting than a closet filled with practical black options. The square toe, the mock brogue details give good friction to anything quite feminine. The balance here of a dress that has all the refinement and prettiness I’m drawn to is fully righted and in my zone when paired with a shoe that has a masculine vibe. This is the balance I’m always striving for - I purposely kept the sole and welt here quite narrow - too much chunk and it would have veered too one dimensionally muscly. This one is….just right.

When I was conducting my “shoe research” in my own closet, I realized the immense satisfaction in a really worn out sole. It felt so good to know that I got such use out of a shoe. Conversely, it really pissed me off seeing how pristine the bulk of my shoes were. No scuffs, no worn in heels. And that’s not because I’m delicate on my feet. My cost per wear was astronomical. On heavy rotation in my closet was the animal printed shoe- but in a modern shape. The print itself is so classic that anything too expected can make you feel a bit basic. But with an exaggerated toe shape, a peculiar footbed - this type of shoe is one I often rely on to give the good strange or dimension to an outfit. Especially when it’s in a material that is decidedly year round, like pony hair. This zebra makes a suit more curious, a classic black dress more interesting, and it grounds a mini by making the whole look effortless. Never trying too hard. The key is that the tones are neutral - it’s definitely a moment without being overly momentous.

So go through your shoe closet and see if you see the same patterns I do. Recognizing the composition of what works and doesn’t will help you make better decisions in the future. And please know this - I love an indulgence. The peach feathered Bottegas from last year are staring at me right at this moment just wondering when I’ll bring them out for a spin. And that’s fine, because these purchases are far and few between. I can recognize now the difference in my goose bumps - the ones that come from the appreciation of sheer artistry vs. the bumps that come as a result of discovering the fine balance of creativity….and pragmatism.