Layer Up With October's Most Coveted Fashion Must Haves

I like a bag that does not overpower my overall look, and this A.P.C. bag ($435) is just that. I love the nod to the '70s with the delicious caramel color and long shoulder strap.

Blame it on Fashion Week's street style crowd — now, I don't think any Fall look is complete without a great felt fedora, like Madewell's floppy version ($75). Is there anything easier, or chicer, to throw on with your jeans and flats?

The only problem with this Gap plaid panel cocoon sweatshirt ($45) is that it doesn't come in every color. For now, I'll take the red version and hope more are on the way . . . as I plan to live in it for most of Winter.

I'm addicted to art deco whatever the season, but as cozy knitwear and simple separates come out for the colder weather, there's never been a better time to invest in a serious statement piece, like the Kate Spade imperial tile necklace ($248). While it may be a bit much teamed with a busy dress, add it to a cashmere sweater or a simple turtleneck, and it lifts a look from boring to "Oh my God, where did you get that?"

When colder weather rolls around, my number one goal is to be as cozy and comfortable as possible, no matter where I'm headed. These Sea silk jogger pants ($355) are chic enough to rock at the office but still make me feel like I'm spending the day in pajamas.

Isabel Marant's next It shoes ($1,130) are here, and like every iteration before them, they're undeniably cool. With every wear, I'm hoping to get that much closer to embodying the brand's effortless Parisian-cool vibe.

I fell for this navy Topshop pleated panel shift dress ($190) from the label's Boutique collection the minute I saw it hit the site. Perfect paired with tights, I'm hoping this will get me through a lot of those uninspired mornings when I'm flinging clothes from my closet, wondering why I don't have anything to wear.

For me, wedding season is far from being over (will it ever really end?), and I've grown a bit tired of sporting the same ol' LBDs. I've decided that for the next nuptial, I'm opting for something fun and colorful, like DVF's blue, long-sleeved jumpsuit ($428). It'll stand out in the crowd without upstaging the bride, and pants mean I can get a little crazy on the dance floor without worrying about a wardrobe malfunction.

My new jewelry obsession? Front-back earrings. They're kind of like your everyday pair with a bit of a twist, and Rebecca Minkoff's pyramid studs ($48) are a great way to wear the trend without being too over the top.

I'm ready to hop on the poncho bandwagon, and I think this Theory design ($555) has just enough edge and just enough structure. The buckle detail underneath the collar is what really seals the deal.

Every once in a while, a dress comes along that is so popular it spans the seasons, reappearing in new styles. This ASOS kimono is just that, and I'm calling it early: this is the easiest dress of 2014. Perennially popular, it must be on its fifth or sixth run, with new colors and prints dropping all the time. For Fall, I love the new dark green option ($80) teamed with black tights and heels.

The moment I spotted Alexander Wang's Fall 2014 collection come down the runway last Spring, I was stuck pining over the crazy color-changing bags. Now, with the new heat-sensitive Rocco duffle ($1,150) on my wish list, I'll never look at a black bag quite the same.

One of my all-time favorite holidays has to be Halloween. Not only do I love dressing up, but it's also an excuse for me to eat as much candy as I want without too much judgment. So, when I saw these Charlotte Olympia heels ($895) from the label's limited-edition collection, I couldn't resist. The candy-filled straps look sweet enough to eat.

Not until I saw Olivia Palermo wearing hers did I really think I needed a denim pencil skirt in my closet. Now, I'm convinced this Black Orchid skirt ($124) will give me the chicest take on denim-on-denim. Ever.

I know a sleeveless vest may seem a bit impractical with cold weather on the way, but this double-pocket vest from Zara ($100) needs to be a part of my life. It's actually a great layering piece for when the temperatures drop.

I spend a lot of time on airplanes, and I'm always looking for that perfect piece to wrap myself in. This Mara Hoffman sweater coat ($374) is cozy and extralong — perfect to throw over jeans and a tee for maximum comfort.

Black and white will never be boring in this Alice + Olivia skirt ($346). The details are crisp, and the asymmetrical hemline is a teensy bit statement-making. The perfect piece to add intrigue when we have to start — groan! — wearing tights again.

While I've strayed toward dainty, barely there chains for a while, I'm now entering a bohemian stage, and I'm ready to get chunk(ier) with my jewelry. This Eddie Borgo tassel pendant ($125) will help me pull off the transition. Plus, it totally conjures images of all the fringe we've been seeing on the Spring 2015 runways.

Although I've been saving up for a real-deal leather jacket for a while now, I'm not quite ready to splurge just yet. This faux option ($60) from H&M looks way more expensive than it really is, keeping my wallet happy and my outfits just as trendy.

Why not inject a little color into our Fall wardrobes by investing in a bright blue bag? I just got this mini Pashli by 3.1 Phillip Lim ($695), and I adore it.

I'm really digging the loafer trend at the moment, and this classic, monk strap pair from J.Crew ($288) looks superchic, not to mention comfy. I think I've found my new go-to shoe.

I love an LBD that can carry across all seasons. This black embroidered dress from Twelfth Street by Cynthia Vincent ($365) is ideal for transitional months like October and March. Perfect for wearing with sandals or layering over tights and boots!

I've never worn an over-the-knee boot, or even a knee-high style for that matter. The truth is, as a short girl, I never thought I'd be able to pull them off. But this Fall I'm throwing all doubts out the window, because I can't stop thinking about these Stuart Weitzman Lowlands ($785).