Fall Booties You Can Stand In All Day & Still Look Chic


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Cropped booties are all over the place this fall and I’m on board with the trend. The right pair of cropped, heeled booties can transition from summer to fall and even go into winter and spring. Plus, if you choose wisely you can score a few pairs that are extremely comfortable. Yes, even I look for comfort sometimes.

I have three brands that I’m loving for fall booties. No, these aren’t bargain brands. Since these shoes are meant to be worn regularly without causing you pain, I’d suggest planning to splurge on the right pair and save the bargain shopping for pieces you won’t wear as often or for as long. I’ve tried all three of these brands and can confirm that even with the heels you can wear them all day foot-pain-free! In fact, they even offer pretty good arch support.


Sofft Wesley Anthracite Distressed Foil Suede Boot

Sofft Wellsley boots are comfortable and stylish
Sofft Wesley Anthracite Distressed Foil Suede Boot ($110, from Zappos)


The stylish silver distressed coloring and attractive stacked heel on these Sofft Wesley Anthracite Distressed Foil Suede Boots is what immediately caught my eye when I was browsing Feet First, an awesome shoe store in New Orleans. Upon closer inspection, I realized they were made by Sofft, a company that’s dedicated to combining fashion-forward design with comfort technology. The color is light enough to be worn with bare legs now, but can easily also pair with jeans or black pants as it gets colder. If you can’t hop on a plane to New Orleans, you can also order these booties from Zappos.

After a day standing on cement floors led to a night of back and hip pain, I wore these boots the next day when I ended up walking a total of about 5 miles all over the city of New Orleans. My feet, back and hips all felt completely fine, making these a definite win!




Vionic Booties

My mom actually told me about Vionic shoes when her podiatrist suggested she try some to help with some foot issues she was experiencing. I ignored her for a while. Yes, she told me they were cute shoes and I generally trust her fashion advice, but if a podiatrist suggested them I pretty much assumed they must be ugly. After multiple mentions from her and my realization that I needed a few pairs of shoes I could wear to factory tours, trade shows, and other all-day-standing events my work requires, I finally checked Vionic out on Nordstrom and, okay, mom was right.

The selection of boots and flats is both stylish and well-made, plus every pair features orthopedic technology to alleviate foot pain and provide proper support.  I ordered the Vionic Windon Weather Resistant Zip Bootie ($159.95) in Natural Snake.

Vionic Windom Weather Resistant Zip Bootie ($159.95 from Nordstrom)

NORDSTROM - Shop Women's Shoe Steals


I love the slight western styling on these boots, plus the weather-resistant nature means they have a little sheen in real life. They are available in black and brown suede as well if you don’t want to go quite as crazy. However, I wore the snake pair last week and got plenty of compliments.


Madewell Classic Black Billie Boots

Madewell Billie Boot (on sale for $175.50 from Madewell.com)
Madewell Billie Boot (on sale for $175.50 from Madewell.com)

I picked these Madewell Billie Boots up on a whim when I was in Miami, it was raining, and the only closed-toed shoes I’d brought were giving me horrible blisters. I wasn’t really looking to spend so much money on a quick replacement pair of shoes, but I really liked these and didn’t see much else to go with the rest of what I’d packed so I decided to splurge. I’ve now had these booties for about two years and they’re still in perfect condition, plus they are extremely comfortable. I throw them on anytime I want a classic, chic look I can wear all day and still enjoy a little heel height. They are on sale right now, so if you’re interested it’s a good opportunity to buy.


  1. Hi Megan! I need help! How do i wear booties with straight-leg/skinny pants? Should the pants just hit the top of the bootie? or do your pants go inside the top of them? Should you be showing a little ankle? WHat about when it gets cold? xoxoxo

    1. Hey Erin great question (and perhaps future post!). On me, since I have a curvier figure, I like the pant to overlap the top of the bootie just a little (this looks best if the pants aren’t super super skinny). I think you would look awesome with the pants cuffed to show a little sliver of ankle (this is my favorite look for those lucky enough to have long skinny legs). If the jeans are dark and really skinny you can tuck, especially if boots are a little loose. In winter you can get away with tucking thick skinny black pants or leggings as well. Also for winter, I’m seeing some cute looks placing a visible thick sock between the boot and pant but have yet to experiment with it on my non model frame!

  2. Ouuuu how fun! I need new boots. I’ve been searching for a pair just like that first one you have. I’m looking for a cute, trendy pair that is also comfortable. I have lovely bunionsđŸ˜”that restrict me from buying the shoes I usually want! Thanks for sharing.

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