To chat about our favorite boots for the fall season, I teamed up with Sarah Collie from District Damsel, a Washington, D.C.-based blog that has showcases how to dress like Vanity Fair on a twenty-something's budget.

Over-the-knee boots have been on every fashionista's Instagram this fall, most likely the gorgeous Stuart Weitzman Highlander boot, which boast an $800.00 price tag. Considering that's close to my monthly rent, they were not even an option for my budget, but I found an amazing lookalike pair for a fraction of the price.

I've always been a fan of the over the knee trend, pairing knee socks with booties to emulate the look, or that time that I bought two different pairs of boots from Rue 21 in college that looked like they were props from the Pretty Woman wardrobe (if you know what I mean.) This season's hot boots are suede and fitted all the way over the knee, which gives it a classier look than leather or boots that flare open at the top.

I like pairing mine with flirty floral dresses or skater skirts, but since they are sexier, I think it's important to balance out the look with long sleeves or a conservative neckline. Personally, I don't think these boots belong in the office, so I would stick to date night or a night out on the town to bring these bad boys out. As Cazey mentions below, "the weak do not wear boots", so if you're going to go for the over the knee look, you better werk that look and own it. Nothing ruins an outfit more than not being confident, especially when you're wearing such a statement-making shoe.

Boots | Steve Madden

Dress | Forever21

Bag | Rebecca Minkoff

Photo cred: Andrea Viza

Many guys lack shoe game. And we’re not talking guys who wear white socks and slip-on sandals. I’m talking rolling up to the bar in sneakers. I say this as someone who used to do the same. Then, one day, I saw a guy in my math class wearing Chelsea boots and knew I wanted those. Of course, at the time I didn’t know they were Chelsea boots, but so began my affinity for boots.

Boots are an easy way to step up your fashion game. They not only look stylish (people will compliment you, I promise), they can add some confidence to your step. The weak do not wear boots.

These men’s harness 8R Frye boots are my go-to boots. Now I know, they’re expensive. They’re Frye. This was an investment and took me many sleepless months and consultations with cobblers to decide to click “Purchase”, but I have never regretted it. I plan on having these for another two decades, and people constantly comment on my footwear. Pair them with almost anything – except business casual. 

After I got my first pair of Fryes, I told myself there was no way I would ever let my wallet bleed like that again. Then I saw these, and I had to have them. So three years later, my wallet and I had a heart-to-heart and out of it came these: men’s engineer 12R boots.

These Penguin chukkas are arguably not boots at all. This style of shoe has a lot of names: Chukkas, Clarks (because Clarks popularized the style in the 1950s for you history nerds), or desert boots. Basically, this is your gateway drug to wearing the real deal. The best part about desert boots? You don’t need to wear pants. By that, I mean you can wear shorts with these bad boys. (Please have some sort of covering)

The question with boots is, of course, tuck or no tuck? If you have baggy pants, please don’t! You look like Sigourney Weaver in Gorillas in the Mist – not what you’re going for, I promise. If they’re skinny jeans, definitely tuck. I don’t think you even have an option. Otherwise, it’s a coin toss. Boots are gorgeous feet shrine that need to be seen, so tuck if you can – but you need to be able to pull it off, which includes feeling comfortable in what you’re wearing.

Harness Boots | FRYE

Engineer Boots | FRYE

Chukkas | Penguin