As one season comes to a close and another one begins, the transition between the two can often feel sluggish. There's a fear of committing to retiring favorite styles of clothing and shoes because they're beloved pieces. But there's also the reality that while one day can feel like fall is here to stay, the next day, warm summer-like temperatures can again demand your attention. In order to embrace the in-between of the next few months with your footwear, consider rounding out your bootie collection with a new pair (or a few) from Target's latest fall drop.

If there is one shoe you're likely eager to bring back into your everyday rotations as cooler weather arrives, it's boots. But riding boots can sometimes feel a bit too warm and constricting as the new season gets underway. Rather than solely relying on flats, get your boot fix with help from booties, which traditionally rise a few inches above your ankle. This season, think about a heeled bootie that's perfect for going back to the office, a clog bootie to embrace the latest trend, and a classic Chelsea boot that will carry you through many seasons to come.

Because Target's boots are typically quick to sell out, we narrowed down the search for you with these nine affordable, comfortable (think: memory foam insoles), on-trend picks.

Fall Booties to Shop at Target:

Shop now: $35, target.com

If you're looking for a bootie that can easily transition from the weekend to the work day, consider the Universal Thread Kennedy Ankle Boots. Available in three colors (cognac, bone, and brown/leopard), the Kennedy has a 2-inch block heel and a 4.5-inch shaft height (the height of the shoe, excluding the heel). The inside of the boots features memory foam for added comfort, and the exterior has a zipper, which makes the boots a breeze to take on and off.

Shop now: $30, target.com

Chelsea boots are perhaps one of the most classic and iconic bootie styles, and the A New Day Ellie Chelsea Boots definitely hit all of the marks of this timeless look. Similar to other booties, the Ellie Chelsea Boots also feature a 2-inch block heel, to allow for a comfortable fit while walking, and a 4-inch shaft height. The boots are available in brown and black, and both include extra elastic to ensure they're easy to take on and off even without a zipper. Keep in mind, shoppers suggest sizing up a half size if you're planning to wear thick socks, or order your normal size if you plan to wear thin socks.

"They are a 5/5," wrote one five-star reviewer. "They are so comfy and so cute. I love how the top of the boot isn't too pointy so your toes can breathe and not be smooshed. The color is beautiful and the heel is the perfect height…If you have these in your cart, check out now."

Shop now: $30, target.com

It's always fun and a bit unexpected to add texture and a light color into your bootie collection, and an easy way to liven up any outfit. And the Universal Thread Sylvie Ankle Boots do just that. Thanks to the shoes' versatility, you can dress these 2-inch block heel boots up and down, which means they're ideal for everyday use. Plus, they have a tab on the back to make taking them on and off a breeze. Shoppers have gone ahead and declared the boots a win because each pair is so comfortable, and they're purchasing them in multiple colors."I took a chance and purchased the black and the beige colored boots. I love them," noted one reviewer. "Whenever I purchase shoes, I know I have to share them with my daughter. We both agree they are very nice and comfortable. Yes, we can walk around in these boots for a good while, as they are true to size and a workable height."

Shop now: $40, target.com