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The Best Shoes and Boots for Fall 2019

by habituallychic

09 . 10 . 19

It’s been cool enough in New York that I’ve started wearing flats and I’ve seen many editors already wearing boots during fashion week. That might be jumping the gun a little but it is a good time to think about your fall footwear. We all know that that by the time you really need a coat or boots, all the good ones have sold out. I’ve put together some of my favorites in many different price points including a few pairs that I bought myself to help get you started.

I love d’Orsay flats and own many pairs. They are a great transition from sandals to real shoes before it gets cold. These green crocodile-effect d’Orsay leather flats are so chic and at the top of my fall must have list. They would look especially great with a black crewneck sweater and black trousers for an office or as a pop of color a tweed blazer and jeans. They are also available in navy.

I posted these Sarah Flint Lana Flats before but they are so good that they deserve a second look. I am mad at myself for not trying her shoes sooner because they have interior padding that make them so comfortable. This style felt a little small in the toe box so I took one half size up. They also come with rubber soles and in navy and black. The Natalie Flats are another great option available in seven different colors and patterns.

I have the leopard version of these suede tassel flats and love them. They also come in black and green and are 40% off with the code STEPITUP until midnight September 10, 2019.

Square toed shoes are having a moment in fashion and most them are terrible. These 90’s flats have a better subtle square toe and are available in seven different colors.

I was so excited to buy burgundy velvet smoking loafers last year but they are so tight that I need to get them stretched again so I can finally wear them. Those of you with narrower feet should consider these burgundy suede smoking slippers. They are 30% off with the code SHOPNOW and come in three other colors.

If you work in an office, I love these modern plaid tassel pumps. They are also 40% off with the code STEPITUP until midnight September 10, 2019.

I also have these leopard calf hair Perfect Pumps. They also have interior padding that makes them extremely comfortable for walking and standing. They also come in eleven other colors and include rubber soles.

These top knot pumps would elevate a grey suit or shift dress for an office job but they’d also be great with grey trousers and an an ivory blouse. They are also 40% off with the code STEPITUP until midnight September 10, 2019.

I love snakeskin shoes for fall but these snake print and suede pumps take the look to the next level.

These pointed-toe color block velvet pumps would make the chicest party shoes for fall. They are 30% off right now with the code SHOPNOW.

I love the olive shade of these suede kitten heel boots. I’d wear them with jeans and an ivory cable knit sweater or tweed jacket but you could also pair them with a long floral dress for fall. They are 30% off with the code SHOPNOW and are also available in black.

I’m so used to uncomfortable boots that I was expecting the same from this Perfect Zip Bootie but I was blown away when I tried them on. The wider toe box means my feet aren’t squished and there is extra padding and arch support that makes you feel like you are walking on pillows. They also have the protective rubber soles that mean you can wear them right away too. I chose cognac suede in the lower heel to wear with jeans and sweaters but they also come with a higher heel and both heel heights are available in black leather.

These pointed-toe leopard calf hair boots are even very chic and 30% off with the code SHOPNOW.

Give your outfit the Chanel-look with these two-tone leather ankle boots.

These black Suede Tassel Heeled Booties would look great with black jeans and with a skirt or dress and black tights. They are also 40% off with the code STEPITUP until midnight September 10, 2019.

Midi length 70’s style dresses and skirts are hot for fall and they look great with knee high boots. These snake-effect leather knee-high boots are my absolute favorite pair.

A more budget friendly option that look high fashion are these Slouchy Block Heel Boots. They also come in black and are 40% off with the code STEPITUP until midnight September 10, 2019.

The chicest of chic boots are these taupe leather knee boots but they are also available in five other colors.

If you’re a fan of floral print midi dresses, these green crocodile-effect leather boots would probably match them all and add a chic pop of color.

Celine sent tan leather and shearling lined thigh high boots down the runway for fall but if you’re looking for a better priced option, I suggest these brown over-the-knee boots in suede. They are also available in black and 30% off with the code SHOPNOW.