Recently, after moving from one tiny apartment to another, less-tiny-but-still-tiny apartment, I had the pleasure of taking on one of life's most annoying yet necessary tasks: Organizing my shoes. My new coat closet has a handful of built-in shelves, and I figured that was the perfect storage solution. I planned to make things simple for myself — the pairs I wore most often would be placed toward the bottom, so that they were easy to grab, and everything else could be stacked above them.
I was somewhere between playing Tetris with all my boots and shoving long lost high-heels into a corner when I made a sad discovery. Despite have a whole collection of fun shoes, I still wear the same eight pairs over and over again, and they're versatile styles that have been in my rotation for years, maybe even decades.
That's not to say my other footwear options don't serve a purpose. My workout routine may currently be slacking, but I know that fitness-type sneakers definitely come in handy (and between weight and other details, that shoe category is a whole separate beast). Plus, I'm fairly confident that, at some point in the future, there will be an occasion where I say "Wait — this is a job for silver stilettos." There's also a few weeks during the the year where I'm thrilled that I own super practical snow boots, rather than having to risk breaking a bone while walking on ice.
However, as someone who works in fashion and essentially shops for a living, often influencing myself to make a purchase, it's surprising that I haven't tried to stray from my go-tos. Even as I experiment with questionable trends like carrot-leg jeans and pully tops, I'm reaching for the same shoes I pair with pleated skirts and leather pants.
Ahead, I'm breaking down the eight pairs of shoes I can't live without. The rest are just chilling on my top shelf.
To be honest, this is a fairly new development over the past year, but I would be lost without UGG boots. I do have multiple pairs, from a short navy blue style to your average chestnut brown option, but after Selena Gomez wore her Bailey Button II Boot on set, I dug mine out from hiding and they're now my favorite pair. While I went monochromatic here, I tend to enjoy the contrast between these shoes and an overall simple or slightly-dressy outfit. I've even worn UGGs with skirts and dresses.
Shop now: UGG Bailey Button II Boot; $180
Dr. Martens Chelsea Boots
For a while, every influencer on Instagram seemed to be wearing these big white boots. At first, I winced at the $180 price tag, but eventually, I caved — and I do not regret it one bit. Sort of like my UGGs, the bulkiness of these babies helps to tone down the fanciness of skirts and dresses, making them seem more casual, but I also reach for this pair when I'm hoping to give jeans and sweats a fashion-forward twist. The lug sole adds a bit of height, which at 5'0, is a welcome bonus for me.
Shop now: Dr. Martens White 2976 Quad Chelsea Boots; $180
When I say I've kept a pair of silver boots in my closet for years, I mean it — I'm pretty sure I bought my first pair in 2015. There's just something about a metallic shoe that adds unexpected flair to any outfit, and I'm even guilty of choosing them over heels for special occasions, including weddings. As long as they're clean, they look kind of retro and fun with an LBD (I've got the proof here).
Shop similar: All Saints Sara Western Boots in Silver, $224.00 (Originally $371)
Sleek White Boots
I know I already included white Dr. Martens on my list, but white shoes have a leg-lengthening effect, so I also keep a thinner, foot-hugging pair in my collection at all times. Even when I'm styling photo shoots, I have to stop myself from adding white boots to every look — they're so sleek and elevated, and mysteriously go with every outfit, whether it's simple jeans or a sequined design.
Shop similar: Marc Fisher Jarli Bootie; $189
I've been wearing Converse Chuck Taylors since high school (middle school?), and a crisp white sneaker is a year-round staple for me. However, the platform feels like a fresh, more modern take to me, and I find they look even better when combined with the current long, scrunched-up sock trend.
Shop now: Chuck Taylor All Star Platform Sneaker; $65
During the pandemic, they've become my preferred dog walking shoes, but before then, my checkered Vans were my problem solvers. They're easy to slip on in a rush, can be worn in just about every season, worked as a neutral, but at the same time, provided a pop of print, taking my outfit to the next level. And, of course, you can't beat that $55 price tag.
Shop now: Vans Classic Sneaker; $50
Despite having a decent selection of sandals in various colors, my most-worn picks of the season tend to be neutral, easy, and versatile. For years, it was all about my strappy gold block heels, but then Birkenstocks came along and took the top slot. They're perfect for both daytime outings and the beach, and after celebrities started styling them with socks, I'm tempted to test them out in colder weather, too.
Shop now: Birkenstock Arizona EVA Sandals; $45
Technically, this outfit is a Halloween costume, but preppy style has had a resurgence and I've started to seriously wear many of the pieces in this photo — loafers included. They're classic and sharp-looking, not to mention are the perfect companion for my khakis and other non-work, 'work pants.' And, once the weather gets a little warmer, I really do plan to throw knee-high socks in the mix, channeling iconic '90s characters.
Shop similar: Brother Vellies Troubadour Loafer in Midnight; $595
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