Planning on going southwest probably means a more tropical destination, certainly, than the Chicagoland area, if you're wearing something like our model is wearing. If you're looking to come to Chicago during the fall, you'll need to wear outfits that are for cooler weather now, because you're likely to come while the frosty northwest winds are causing a frigid wind chill this fall.
So being the tourist in Chicago now means going to museums, perhaps, because the fall colors have brought weather that doesn't include wearing sandals and transparent or airy tops. Spending the day in the Art Institute on Michigan Avenue certainly doesn't mean bundling up inside but getting there, whether by taxi, your own car or public transportation does mean wearing, at the very least, fall jackets and slacks or tights. You may see a Chicagoan wearing boots, either ankle boots or the longer version, up to the knee. She might wear a trench jacket over a sleeveless top inside, since layering really is the fashion these days, or a lacy sweater like our model is wearing for a quick stop outside. However, if you're dressing to be comfortable and plan to go outside for a while, a leather trench jacket with a hat and gloves would be appropriate to wear, of course.
If you're planning a trip to Los Angeles or another western destination, layers will be good just in case the temperature dips a little bit but the palm trees won't be withering like some of the outdoor plants might be in Chicago. Taking the withering plants in here, if it means working on the porch or deck, if that's where your garden is, will certainly mean wearing a sweatshirt or a heavy vest.
If you don't have outer layers yet, now is a good time to shop for outer layers. Black and white are certainly stylish colors and designers like Calvin Klein are definitely featuring black for the fall. A dress like a Ralph Lauren can be used to dress up or dress down with the right separates, increasing your outfits if you use separates. With that in mind, checking out some Lee jeans at Sears may not be glamorous but it will be a staple for your wardrobe if they fit well. So even if you're only heading out to the southwestern suburbs of Chicago, layers will work, of course, this season.