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Womens/Shoes/Flats
Top 10 Pointed Toe Flats

Comfortable, Feminine Flats To Go With Every Look

Comfortable, Feminine Flats To Go With Every Look

The perfect flat is hard to find, especially when you introduce a pointed toe silhouette. You want it to be comfortable and offer a bit of support without looking extremely bulky. We aren't ones to sacrifice style, so we had the Rank & Style algorithm find the best pointed toe flats under $100. Whether you tend to reach for the ballet-inspired flat or opt for the classy D'Orsay style, the following flats won't break the bank and will last season after season. Some are so chic that they're a great replacement for heels on special occasions, and some will pair effortlessly with your casual jeans and t-shirt looks that will then be elevated to a sophisticated level. Whichever you choose, your feet will thank you! And if you need extra support, don't fret. All easily accommodate a slip-in insole! Opening image: @rothys

Love our 10 Best Pointed Toe Flats Under $100? Check out our 10 Best Comfortable, Stylish Walking Sandals for more top-ranked finds!

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May 29, 2019

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Top 10 Lists serve as unbiased shopping guides to the most trusted product recommendations on the internet. Products are scored and ranked using an algorithm backed by data consumers find most valuable when making a purchase. We are reader-supported and may earn a commission when you shop through our links.

The Rankings


Old Navy d'Orsay Flats

Our Score

STYLE WITH: Go classic and cool with a pair of cropped jeans and a white button down.

FUN FACT: This style of shoe was designed to be worn by men, with the cut-out sides being used to accommodate wider feet.


Bella Vita Vivien Pointy Toe Flat

Our Score

USERS SAID: "These are the most comfortable flats I've ever owned. They are incredibly soft, yet supportive. I wear 8 hours a day at work and now own 3 pair. Bought many, many flats through the years but, honestly, these have been the best!"

BEST FOR: These simple, classic flats are perfect for both your workday and cocktail hour.


Marc Fisher Analia Pointed-Toe Flats

Our Score

LOVED FOR: A simple yet subtly feminine silhouette 

HELPFUL TIP: These shoes run small and narrow, so size up.


Caslon Luna Pointy Toe Flat

Our Score

WHY YOU NEED IT: These preppy tweeds will inspire your inner Chanel for under $25.

USERS SAID: "I walk a lot at work. I was able to wear these for an entire shift without any discomfort. They really dressed up my outfit. I’m planning on getting the same shoe in different colors."


BP Sasha Flat

Our Score

WHY YOU NEED IT: The Sasha flats come in two neutral colors that will get a ton of wear in your wardrobe. 

HELPFUL TIP: Simply slip in insoles if the flat doesn't feel supportive enough on its own.


Naturalizer Samantha Half d'Orsay Flat

Our Score

LOVED FOR: A flat that's as comfortable as it is classic

BEST FOR: Being on your feet all day


Steve Madden Feather Loafer Flat

Our Score

USERS SAID: "The quality and style of these flats is just gorgeous, and I love the modern take on the classic loafer with the pointed toe and raised seams... These feel like a dream to walk around with and don't pinch anywhere, and the rubber sole will be especially great for lots of walking."

STYLE WITH: Embrace the street style look with a printed blouse, pleated midi skirt, and pair of statement earrings.


Free People Royale Pointy Toe Flat

Our Score

LOVED FOR: A unique, boho design that you can wear with pretty much anything

STYLE WITH: Keep it casual with an oversized sweater and a pair of skinnies.


Sam Edelman Rodney Pointy Toe d'Orsay Flat

Our Score

USERS SAID: "I wore these flats all summer and loved them. They are stylish and super comfortable. The elongated shape and pointed toe makes them elegant but still wearable all day. Can dress them up or down."

LOVED FOR: A silhouette that exudes sophistication and can be dressed up or down


Rothy's The Point Flat

Our Score

WHY YOU NEED IT: These flats are versatile, designed with sustainability in mind, machine washable... The perks go on and on. 

AS SEEN ON: You too can dress like royalty with these Meghan Markle-approved flats.

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