It's not unusual to swap out clothing between warmer and chillier seasons, but if only the weather itself was as consistent and organized. It can be frustrating when you just put away your colorful summer shorts for the fall, and bam, it's 75 degrees. Although we can't control the weather, there are certain key pieces you can use in your wardrobe to make the transition smoother.


The Jacket to Layer: Riley Moto Jacket

This chic piece is the epitome of versatility. Because it is 100% organic cotton, it’s easy to fold up and stash in a bag; plus, the sleeves can be rolled up when it’s warm. (Conversely, it would look great layered under another jacket or coat. Think of this jacket as a removable liner to your other coats.) Being a neutral color, it will go with absolutely everything, but it also doesn't scream either summer or fall color schemes.

The asymmetrical zipper provides a nice contrast to a straight button-up or zipper on another layering piece. There’s a lot of talk about mixing textures this fall, and this is a safe, easy way to take on that trend.

$190; available at Perchance, 11 E. Walton St. (at State), 733.244.1300


A Scarf for Every Season: Chan Luu Scarves

Because these scarves are made with 70% cashmere and 30% silk, they are lightweight, keeping you cool in the heat while also keeping you warm in the winter. Available in 17 colors, there is bound to be a color to suit everyone. Virtu only keeps one of each color in stock in the store, so it’s best to call beforehand to secure the color you want.

As for different ways to tie them, there are some helpful ideas on Refinery 29 and The Fashion Spot.

Truly, a scarf helps pull together any outfit and is amazingly easy to stash away (which, we all know, is key).

$172; available at Virtu, 2034 N. Damen Ave., 773-235-3790


Versatile Sweaters: Any from Krista K

No matter your personal taste in sweaters, Krista K has a wide variety of styles and fabrics to choose from that will work in practically anyone’s wardrobe. The options are stock full of smart lines, clever embellishments, neutral colors, leather details, Merino Wool, cashmere (and who doesn’t love cashmere?) and more. These sweaters are interesting without forcing themselves to be the focal point of an outfit.

Any of these knits can easily be layered over long sleeve shirts and peek out from under cute jackets and blazers. When it’s a little warmer, they can be thrown on over a tank or flowing dresses and skirts. If wearing a dress, it’s probably best to go with a cropped sweater, as to not lose a waistline, depending on the cut of the dress.

$108 – $455; available at Krista K, 3458 N. Southport Ave., 773-248-1968


A Second Pair of Tights: HUE

No, it’s not rocket science, but wearing two pairs of tights at once is significantly warmer than just one. They give you the warmth of leggings without the extreme casualness, and look sleek and put together with dresses and skirts. Not to mention, tights are much better to wear under skinny jeans than long underwear because they don’t bunch up. They also cover your feet, providing another layer, whereas long underwear often doesn’t. You can take off the second pair if it gets to warmer without impairing the look of an outfit. Options!

$13.50; on the HUE website, enter your zip code to find local retailers where HUE is available.


A Functional Carry All: Garrison Bag

Winter Session was founded in Chicago in 2010, but now base their business out of Denver. Lucky for us, two stores in Chicago sell their Garrison Bag (above). Their goal is to create bags that are “a balance between utilitarian function, durability and aesthetic appeal”. Not only are their bags functional, but also they have a classic, clean look that will go with your everyday outfits.

The great practicality of the bag is, of course, that you can store, tie, and stuff your belongings on and into it. It’s decorative to tie your scarf onto the strap when you aren’t wearing it around your neck, on your head, or many of the other ways provided above. The trick is to twist the scarf around the strap enough times so that it doesn’t look floppy. With many pockets, you can stash and store with ease. There is even a pocket specifically sized for a phone or iPod.

Because of the bag's durability, you don’t have to worry about adding too much weight, or about it getting ruined/worn out in the elements. The Garrison Bag has more than enough room to stash extra tights or hide away unwanted layers. Each bag has a snap hook key holder so that you never have to worry about losing your keys in a large bag.

$255 – $285; available at Winter SessionThe Haymaker Shop (5507 N. Clark St., 773-681-0798), and Morlen Sinoway Atelier (1052 W. Fulton Market, 312-432-0100)


Soft, Simple T-shirts for Layering and Warmth: Michael Stars T-shirts

These cozy T-shirts come in a variety of colors, including the popular gem tones of fall. The long sleeve shirts would look great layered under a knit (as mentioned above). Cuff the knit and not the shirt for a cool, easy look. Cuffing sleeves almost always makes an outfit look more put together.

Because of how soft these shirts are I often wear them to sleep in and then simply throw a sweater on in the morning before heading out the door. Viola! Easier mornings.

$39 – $120; available at Art Effect, 934 W. Armitage, 773-929-3600