I am a shoe gal through and through. They can truly make an outfit and as a New Yorker I put my shoes to work so I’m also sharing in this post how I take care of my shoes + protect them. I invest in my shoes and always want pairs I’ll wear again and again. The shoes below – most of them I’ve had for over five years (it is wild to see how much the prices of many of them have gone up in that time!) and I hope you’ll find this post helpful as you build out a shoe collection you love.

This post has been updated to include my recent additions.

My Favorite and Most Worn Shoes + How I Take Care of Them

White Sneakers

I was convinced to buy these Common Projects sneakers after seeing my friend Jenny always looking so casually cool and put together in them. They are perfectly slim + sleek meaning they literally go with everything I own. I love these sneakers and have worn them an almost embarrassing amount of times since getting them in 2018. I now bring them on pretty much every trip since they are so versatile.

A head’s up that the sizing on the sneakers is funny – I took them in a size 36 when I’m usually a 37 in European shoes. A full review of them is here along with some more affordable look alikes.

Khaite Sneakers

Another favorite pair of sneakers I added to my collection that are a bit more sporty are the Khaite suede paneled low top sneakers. They are perfect to style with dresses or trousers and I’ve even worn them with leather pants for a juxtaposition. I took a half size down to a 36.5 as that’s all they had (they sell out regularly – it took me a year of waiting to have these restocked till I got them!) and they fit perfectly. I could have probably done a 37, too however.

Gucci Mule Loafers

These Gucci loafers are a great staple mule shoe as I think they elevate any outfit. Better yet? They go with pretty much every one of my favorite pair of jeans. I sized up to a 37.5 in these.

Low Block Heel Sandals

I really love the Stuart Weitzman Nudist sandals and they’re usually my go-to for weddings and fancier events during warm weather. But after experiencing some low back issues earlier this year, I started wearing my Nearly Nude sandals with a stacked heel pretty heavily. I wore them to every wedding I went to this summer and with countless other dresses for more casual affairs. These shoes are so comfortable. They’re the perfect height, they are great to walk in and they come in loads of colors. I can’t say enough about these as a worthwhile investment for a comfortable heel.

If you prefer a lower heel, too they have this pair.

This pair is another I love for comfort and style.

Chanel Heeled Slingbacks

Every year for my birthday I buy myself a gift and a few years ago it was the Chanel slingbacks. I thought about these shoes for several years, tried them on several times and never bit the bullet. Now, I can’t imagine my shoe collection without these because I wear them so much! They elevate every outfit and can go with jeans just as easily as they can a pretty summer midi dress. They’re comfortable because of the low, stacked heel and can put up with the many steps I take in them running around. If you like the style and not the price, this and this are more affordable options.

Chanel Flat Slingbacks

The Chanel flat slingbacks are a more walkable version of their famed style and I particularly love how they pair with jeans.

Booties

These booties were the best pair of shoes I bought in 2017 and remain a favorite many years later. I can go for miles and miles without any issues with these little booties and I love styling them with both jeans as seen here or with dresses. I get compliments on them whenever I wear them and truly find myself reaching for them in Fall + Winter at least twice a week. They also come in a gorgeous cognac color and in leather.

A more affordable version is available here.

Knee High Suede Boots

The Sarah Flint Alexandra Boots are so perfect for a walkable boot you want to wear with dresses and skirts. They have some good stretch with the suede shaft and the tortoise heel is a special detail that makes these standouts.

Chanel Ballet Flats

These Chanel ballet flats were another investment pair of shoes I thought about for a long time before I actually bought them in 2016. I treasure these shoes and the sentiment they hold as I bought them while in Paris just before I started my self employment journey. They remind me of a time where I was full of hope and excitement and they always remind me of one of my most special trips to Paris. These flats are so comfortable, have the prettiest design that goes with so much and make any outfit look a bit more dressed up.

I consider these a signature shoe for me and reach for them so often.

I also have them in black:

Over The Knee Boots

I first got these boots in 2014 and while I wear them less right now – I know they’ll be back in style again so I keep my black pair and my brown pair tucked away. These are great to travel with because they collapse down easily. The quality and comfort makes them worth the splurge. They stay up over the knee (a lot of inexpensive brands will constantly slouch down taking away from the elongating illusion over the knee boots are good for) and they’re great over jeans or with dresses. 

Suede Knee High Heeled Boots

These Larroude boots are gorgeous and so comfortable. They pair beautifully with dresses and skirts.

Converse All Star Sneakers

I bought the Converse All Stars in black after seeing French girls style them in so many cool ways. They are perfect for wear for me in Paris and New York in Fall & Winter. I love that you can now also customize the colors on each pair you get when shopping on Converse.com.

Timeless Loafer

A comfy, buttery leather loafer never goes out of style. I love this affordable pair by Sam Edelman.

I also have the investment pair by Gucci:

Errand Sneakers

On weekends I reach for these sneakers a lot. They’re more stylish than a pair of Vans, they’re super comfortable and they’re great with jeans or, let’s be honest, leggings. They’re my go-to for going to/from my workouts and running errands in my neighborhood. 

Espadrilles

These comfortable espadrilles look just as good with jeans as they do with dresses and skirts. I’ve worn them so much in the Spring and Summer. They are super comfortable and look designer without the designer price tag. They come in a variety of colors and heel heights, too. The flat pair is on my list for this year. 

I also have the black pair.

The Perfect Pump

One of the most comfortable pairs of heels I own = the Sarah Flint Perfect Pump. Expertly crafted with comfort in mind, the soles feel like little clouds which makes scooting around town easy, breezy in these. I also love that they come in three heel heights and multiple colors. I own the Black, Taupe, Espresso & Red. 

Veja Sneakers

These Veja Esplar sneakers are a more affordable alternative to my Common Projects and I got them in a beautiful brown suede to wear with all my ivory sweaters in the Fall and Winter. They’re not as buttery soft as my Common Projects by any stretch but you can wear them in and get them feeling good in no time. They are a great shoe for travel as they can go with jeans and/or skirts and dresses. I also own them in the Black colorway.

Kitten Heels

These little kitten heels allow me to feel put together and dressed up but don’t sacrifice comfort. I size down to a 6.5 from my usual 7. This pair is similar.

The Feminine Flat

The Sarah Flint Natalie Flat is a go-to shoe for me for its feminine silhouette and comfortable design. I own this shoe in multiple colors and have blogged about this great shoe here, here & here. I reach for these flats time and time again – they are so worth the investment. (I have 3 colors!) 

The Staple Sandal

The Hermes Oran sandal are the most effortless summer sandal to wear with everything. 

A more affordable lookalike can be found here.

The Sporty yet Chic Sneaker

These APL Techloom sneakers were a best buy of 2019 and I haven’t stopped loving wearing them. They are so comfortable and I love that I don’t have to wear socks with them. They are the shoe I reach for every time I am heading out for a long walk, going on a light hike or want to be extra comfortable in a sneaker that doesn’t sacrifice style. I sized down half a size to a 6.5.

The Suede Heeled Bootie

These heeled Marc Fisher boots are so good for Fall and Winter that I now own them in two colors. They look as good with jeans as they do dresses and are comfortable for toting around town.

Chic Snow Boots

My favorite boots for Winter, these Marc Fisher boots are as stylish as Winter boots come. They are warm, so chic and crazy comfortable. They sell out every single season for good reason. I now own them in two colors. 

The Sleek Neutral Sock Bootie

These Inez booties are so comfortable and I love the perfect neutral color of them. A full review can be found here. My new code for 15% off your purchase is WITWHIMSY15 when you purchase using this link.

Golden Goose Sneakers

My favorite sporty-chic sneaker. These Golden Goose sneakers are so easy to slip on and I love how they look with everything from skirts to dresses to jeans and leggings. I own a pair with silver and also brown. Definitely some of my most worn shoes. 

The Walkable Neutral Bootie

A low heel makes these Rag & Bone boots easy to trot around town. They are extremely well made and comfortable. They’re the perfect neutral color to wear all year round, too!

The Dress Bootie

Every girl’s closet needs a pair – the perfect dress bootie to wear all Fall & Winter. This pair is so sleek and yet comfortable. I reach for them particularly during the Fall and during the holiday season as I love how they look with little dresses and tights.

Manolo Blahnik Maysale 50 Kitten Mules

These heels are so timeless, so chic and truly the perfect ladylike shoe. Whenever I share them on social media I always get questions about their comfort. These are *not* my most comfortable shoe. Heeled mules in general are not a shoe I would reach for when it comes to wearing them for a long period of time or when I am planning to do a lot of walking. These are much more a shoe I wear out to dinner, to an event or that I’ll throw in a tote and swap into as I reach my destination if I plan on doing a lot of walking beforehand. 

I don’t find they slip off and have truly had no issue walking in them – but keep in mind every foot is different! I just walk more slowly in these then I would a lot of other go-go-go shoes on this list!

I sized up half a size in these.

Manolo Blahnik Ballerimu Mules

A chic and timeless mule in a great neutral. I love the modern take on the ballerina flat of these Manolo Ballerimus.

I sized up half a size in these.

I have a similar pair by Margaux as well.

I sized up half a size in these.

The Waterproof Lug Boot

Water resistant suede? Yes please! These Freda Salvador boots are so lightweight making them perfect for travel and oh so practical. Super comfy, too. I wear my true size. If you’ve never bought a pair of Freda shoes before, you can use code WITWHIMSY15 for 15% off!

The Riding Boot

I looked for what felt like years to find the perfect riding boot. I wanted something unbranded (read: no logos!), something that felt really timeless, was comfortable and was slim. When I saw these Khaite Riding Boots I loved them but not at their price point. But by some stroke of luck and a tip from a friend, they were briefly marked down on Saks during one of their sales and I scored them for over 40% off. 

I took my usual size 37 in these and I did have to bring them to my cobbler to have the shafts stretched as I found them rather narrow.

. . .

Love my shoe collection? Shop My Bag Collection and My Favorite and Most-Worn Jeans.

Now, onto the care of my shoes as I get asked about this a lot over on Instagram! As you can see, I buy rather nice (and therefore pricey) shoes and I do this because of comfort and because of longevity of wear. If I’m dropping a lot of $$$ on my shoes I need them to last – a long, long time. And, living in New York City, I walk a ton. I really put a lot of miles on my shoes – particularly those showcased above.

When I was first introduced to the concept of adding a protective sole to my shoes before I wear them it was a game changer for me. I’ve been taking my shoes to Firm Shoe Repair in Union Square for over a decade and upon repairing a few pairs of my shoes the guy told me I really needed to be getting protective soles put on before wear not when the sole starts to have already worn down. He told me most shoe manufacturers don’t put proper soles on the shoes so that they wear down faster and have you purchasing more. Adding a protective rubber sole protects the actual sole of the shoe and will allow for you to really get a lot more use out of the shoe.

It is insane how much this piece of rubber helps.

Now I get the rubber sole added immediately when I buy a nice new pair of shoes and have faith afterwards that I can walk a ton in them. It’s what has allowed me to keep wearing shoes like my Chanel ballet flats for 6+ years. Protective soles also help when wearing your shoes out in less than desirable weather like rain and snow. If you don’t have a protective sole the water can seep in through the stitching and cause damage and break down threads and leather.  The $10-$15 addition of the soles will save you a lot of money in the long run.

If I buy suede shoes I often ask the cobbler to weather proof them as well while I’m in getting the protective sole. Alternatively, I’ll use something like Scotchguard or a spray like this at home to further protect the fabric and ensure I’ll get longevity out of the pair. (Weatherproofing your shoes will go a long way in easing any anticipated anxiety of being stuck commuting when the skies suddenly open up with rain or it begins snowing before you do, in fact, make it home.)

Other helpful tips for longevity on your shoes?

I keep my investment shoes in their boxes to avoid dust getting on them and when I travel with them I always pack them in their duster bags and keep tissue in the shoe so they don’t get smashed and out of sorts.

In short, all these extra steps are worth it. More than half of the shoes shown above I have owned for more than 5 years and they still look rather close to brand new. (I was prompted to share all these things after someone remarked on how my Chanel ballet flats looked brand new still when I was wearing them in Paris the other week!) Good thing, too, because I love wearing each and every pair ;).

I do these days miss my former affinity for stilettos that I used to wear way more often but these days I choose comfort and function over fashion. (My mother always told me this day would come…!)

Shop My Shoes

 

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