Ah, Spring in Chicago. Does it exist? No, actually. Not really. In the Midwest, we basically shift back and forth between winter and summer until it evens out. Until that happens, getting dressed is all about the art of transitional dressing. I’ve pieced together three different outfits that work well no matter what the weather (okay, outfits that will work when it’s cold in the morning and blazing by noon).

A shift dress is the best way to tackle crazy weather. You can throw a coat on in the morning and it’s light and breezy enough for the afternoon. While I’m normally an all-black outfit person, another neutral is okay (in this situation). Pair it with over the knee boots for a comfortable but sexy look!

Over the Knee Boots (Similar Style), Tobi Alecia Shift Dress, Christopher Kane Buckle Clutch

This top is one of my favorites because it tackles a cut-out shoulder, without being off-the-shoulder (which is already a bit over done). That also means it technically has sleeves and is warmer than some of my teeshirts for chilly mornings. With an asymmetric skirt and a snake skin sandal – it’s a crowd pleaser that also keeps me from being too hot once the day warms up.

H&M Skirt (Similar Style), Tobi Bethany Cold Shoulder Choker Top, ASOS Snake Skin Sandals (Similar Style) 

Of course – a wrap shirt and a high-waisted skirt is perfect for transitional weather. This top is perfect with a tank top underneath it for the office, or a bralette under it for after hours. Pair leopard with stripes for an unexpected, but coordinated, effect.

Striped SkirtTobi Draped in Tunic Top,Leopard Boots (Similar Style), (Similar Style)

I’ve been spending my chilly evenings inside and dreaming of rosé along the Chicago riverwalk, browsing websites and shopping for summer Friday’s. One of my favorites has been Tobi.com, where I found a lot of inspiration for these looks. If you try any of these looks until it warms up completely, be sure to let me know!

This post was generously sponsored by Tobi and clothing mentioned was gifted. Opinions remain my own. Thank you for supporting brands that make Haute Tempered possible!