I love the pleats. Somehow, they make the bag look more feminine. I think because of the shape, without the pleats, it would look like a bowling bag. I knew a girl in high school who used to wear bowling shoes to school. That’s cute and all—when you’re in high school. Let’s not allow bowling fashion to become a trend, mkay? The Bea is made from 100 percent coated nylon, so it will stand up to the fall and winter weather. It has leather trim, and a satin lining inside. The interior also has an inner zip pocket, and a few slip pockets. There’s also an extra little detachable purse that could be used to hold change or a few small cosmetic essentials. At 15 inches wide, 11 inches high, the purse has enough room to hold anything else you may need to carry. The bottom has little feet to keep it sturdy and clean, the top zips closed, and the dual handles give the bag a 7.5-inch drop. Get it for $385 at Piperlime.com.

Budget Saving Alternatives

If you’re saving up for a vacation to warmer climate once the weather turns nasty, take a look at a couple of lower cost options. I’ve talked about Harveys Seatbelt Bags before. The novelty hasn’t worn off for me yet. They’re made from real seatbelts! I think that’s very cool, the epitome of creativity. This large satchel is called Forever in Blue Jeans. Whoa, hold on. The Harveys people named a handbag after a song by Neil Diamond that probably only my grandma would listen to? I mean, that’s the only way I know that song. I would never listen to Neil Diamond on purpose. Really! Ahem. Moving on. I like that rather than using just one color belt, this bag is a pretty combination of classic fall and winter colors—navy, gray, and icy blue. The flat bottom has feet for protection, and there’s a top zip closure. The interior is fully lined, and boasts a back wall zip pocket, as well as a few slip pockets for smaller things. Dual shoulder straps offer an 11-inch drop, perfect for shoulder carrying. Buckle up for $142 at Zappos.com.

Sometimes simple is best. There’s not always a need for a standout bag, especially if there’s some element of your ensemble you’re trying to highlight. No one wants to be upstaged by their handbag. If that’s the case, consider the Hobo International Lola shoulder bag. Sleek lines, and a slender silhouette accentuate this classic shape. It’s made from 100 percent leather, glazed to give it a nice sheen. The interior lining is polyester, with a back wall zip pocket, and wide slip pocket just below it. It’s 12 inches wide and 7 inches high, with an 8-inch drop. I like this indigo, but it also comes in olive, which looks more like tan to me, and a color called tmoro, which is, uh, brown. Way to confuse one of the most basic colors, guys. Take Lola out for a spin for $138 at Endless.com.