I remember when tall boots were just starting to come back into fashion and everybody started tucking their jeans inside the boots. I wondered if this was something I’d ever really do since boots were already hard to fit with my thicker calves. Then skinny jeans happened, which was nice because there was less bulk to stuff into those boots. The best thing ever was when I discovered a brand of tall boots that had wide calf and fit me perfectly. I now own multiple pairs of this brand, and don’t see it stopping anytime soon (seriously, they’re that awesome).

Earlier this year, I went out to New Jersey for a quick 2 day trip. Since it was such a quick trip, I wore these boots on the flight, and packed a couple outfit that would also go with them. Thanks to a couple nor-easters, that trip became a bit longer so off to the store I went. As I looked for other business casual outfits to wear the following week, I knew that they had to go well with these boots because it was literally the only pair of shoes with me. Thanks to a weekend of shopping New York City, I was successful in this endeavor, and found a few great winter outfits.

Now that the weather has cooled down, I’ve enjoyed pulling these boots back out of the closet and even packed them for my most recent trip to the east coast.

So what are these magical boots? They’re the Sam Edelman Penny Boots (available in regular and wide calf). One additional reason that I love these boots is that they also come in a wide foot. I ordered my boots in both wide foot and wide calf.

On this most recent trip, I channeled some great fall colors to pair with these boots. I got these DL1961 Olive Jeans (similar) last year during the Nordstrom Anniversary Sale. The ones that are currently available are similar, but they have a frayed hem instead of a sewn hem.

I bought this top from Loft earlier this year. Unfortunately it is no longer available; however, Loft has lots of other great blouses currently on their website.

I use a Louis Vuitton Palermo GM whenever I travel because it can hold everything. This large size also makes it a great laptop bag for everyday use. This bag is discontinued, however, there are often a few available on Fashionphile. If you’ve been around here a while, you probably know how awesome I think Fashiophile is. Make sure to check out their discounted section as well (bags get marked down once they’ve been on the site for 30 days).

I look forward to wearing this outfit throughout the fall (and into the winter, although I’ll need to add a jacket for that). The great fall colors pop in this outfit and it is super comfortable. What is your favorite way to wear brown boots?