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Naughty Monkey Untamed PumpsA glossy pump is a year-round essential, but only during these colder months do fabric shoes receive the same love. These, by Naughty Monkey, combine the luxury of a soft, tweed-like material with the simple, earthy elegance of dark tan synthetic leather. The vamp is adorned with a shapely bow, a cute touch that keeps these heels from being too conservative (you can thank the five-inch heel for that, too). Great with jeans or, if you’re so inclined, at the office, these heels work overtime to deliver fall-perfect style.

$79 at

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It finally started feeling like fall here in the northeast this week and nothing makes me happier than crisp, autumn weather. Why? Because it means that it’s officially boot weather.

To celebrate, I stepped out this weekend in my brand new Timberland Earthkeepers™ Rudston Waterproof Pull-On Boots for a full schedule of some of my favorite fall activities: shopping, eating, pumpkin picking, and walking around town soaking up the fresh air. Not only did my new boots look great, they were also super comfortable — even after two full days of a lot of walking.

I knew these boots were going to be comfortable, thanks to the anti-fatigue footbed and sturdy 2.5 inch heel, but I didn’t expect them to be quite so comfortable after so much walking. Add to that the fact that they are made of full-grain waterproof leather and I may not take them off until summer.

Available in 4 colors, $220.

Timberland® Go out and be you™ Click here to shop now!

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Dr. Scholl's Bobbin BootsThough it’s a label renowned for its comfort footwear, Dr. Scholl’s also turns out a pretty stylish boot. These feel a bit sporty and rugged, yet also exude a certain ladylike quality thanks to the fold-over tweed cuff. It’s an unexpected detail that looks great with the boot’s dark, distressed leather. Also in black, dark grey and taupe.

$79 at
ASOS Strictly Lace-Up Block Heel ShoesOne of the season’s most desirable shoe styles, the lace-up heel is a fabulous addition to your fall wardrobe. This particular version is all dressed up in a low-key tartan print and built with a sturdy stack heel for additional comfort. They’re perfect with nearly anything, from daytime-appropriate skirts and dresses to your weekend basics.

$78.57 at

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Cole Haan Air Tali Lace Ballet FlatsSensible they may be, but there’s nothing Plain Jane about these gorgeous flats. That’s right - gorgeous, and that’s a word rarely attributed to the basic ballet flat. With its patent-dipped toe and cool teal hue, though, this shoe is a standout. Naturally, it also possesses the ever-important Nike Air technology for extreme comfort, so it offers both immense style and practicality with every step. In five colors.

$148 at

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