I have long considered shoes the most important finishing touch to any outfit. The right pair of shoes can make or break a look in my opinion and so often it can be easy to wonder which shoe goes with each outfit. It is why I have also built out a closet of timeless shoe styles that I have worn for many years. It’s also why I invest in brands that make high quality shoes that put up with lots of wear. As a New Yorker I walk thousands of steps every day and my shoes need to be able to hold up.
If you’re looking to invest in your closet and build out a shoe capsule wardrobe of essential styles, you’ll find today’s post helpful.
27 Must–Have Shoes For Women
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. I wear them with dresses, with shorts, with jeans – you name it. I wore my first pair so much over three years that I have since bought another pair.
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.
Another similar style to consider: the 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.
A sleek, stylish white sneaker is truly a shoe every woman should own.
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 for the past several summers 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. I can’t say enough about these as a worthwhile investment for a comfortable heel. My style seems to always be sold out nowadays but I did spot this similar style the brand is making now.
If you prefer a lower heel, too they have this pair.
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.
Woven Leather Sandals
I rely heavily on a pair of cognac sandals and a pair of black sandals to pair with all my favorite summer dresses during warmer weather. The YSL Tribute Sandals are sleek and timeless in style. They are not my most comfortable but they are good for shorter outings.
Per recommendations, I sized up half a size to a 37.5 in these.
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 wear them with jeans, with shorts and with dresses.
I consider these a signature shoe for me and reach for them so often.
I also have them in black:
I love a metallic sandal with a small heel when I want a dressier sandal with a particular look in warmer months. This pair checks all the boxes I want in a fancy sandal.
Suede Knee High Heeled Boots
These Larroude boots are gorgeous and so comfortable. They pair beautifully with dresses and skirts.
Converse All Star Sneakers
Love a sportier sneaker? There’s a lot of reasons the Converse All Stars have been iconic sneakers for decades.
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. I made myself a pair of all-white ones to wear during Spring and Summer.
As the shoes are unisex be sure you consult the size guide before ordering!
The Calf Boot
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:
You can get the look for less with this Sam Edelman pair.
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.
I also have the black pair.
The Perfect Pump
An iconic shoe in any woman’s closet. I love how a pointed toe pump elongates your leg and can go with jeans, skirts and dresses.
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.
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.
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.
Related: The Best Shoes for Summer
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. APL has so many styles and colors, too if my pair aren’t your vibe.
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
My number one choice for shoes for Fall is a comfortable heeled sock boot.
You can use code WHIMSY15 for 15% off your purchase of Inez shoes.
I also have a a pair in black that get a lot of wear. 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.
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! I took my usual size of 37.
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.
This style also comes in a lower heel height if that’s your preference.
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.
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.
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!
Also available here.
I also have a similar Lug Sole Boot in leather as well.
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.
The Slouchy Knee High Boot
These knee-high slouchy boots are great on-trend for 2023 boots. They hit right at the knee so pair well with skirt and dresses that are a bit more casual.
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