Transitional Wardrobe Essentials

I have to come out and say it: Chicago’s weather is weird! I don’t know where many of you live, but it’s hard to decide what to wear when one day it’s 75 degrees and hot and the next it’s as cool as 58 degrees. If you’re a fellow Chicagoan, you’ll definitely know what I mean. I’ve enjoyed summer and I’m anticipating fall (especially now that it’s September!), but this jumping around makes it difficult to dress one’s self. To make the whole process a little bit less of a headache, today’s post rounds up some transitional essentials for every gal’s wardrobe. P.S. Scroll all the way down to immediately shop my picks!

Mules and loafers

I know, I know, more talk about mules and loafers but I honestly can’t get enough of them. I wear loafers often and mules are slowly growing on me. The one pair I own was a saving grace during New York Fashion Week (more on that soon), but I actually have my eye on this pair from Free People. I’ve tried them on and it’s just a matter of deciding whether I want black or nude (I truly want both)! Mules are especially great for summer to fall weather because they cover half of your foot and are way too easy to quickly slide on. I’d call that a double win.

New denim

Of course, with colder weather, you no longer have the option to wear shorts so denim is a necessity whether you like it or not. For me personally, fall’s arrival is always a good reminder that it’s time to invest in new denim. I recently snagged my favorite black TOPSHOP jeans from Nordstrom for just $40. I’m also a huge fan of J.Crew’s high-waisted denim, particularly if you have a more athletic build. Just note that the washes fit differently and in general, their denim stretches out so get a size too small and I promise they’ll stretch out.

Cardigans and light sweaters

Don’t break out the wool sweaters quite yet! Fall is all about cardigans and lighter sweaters that you can layer with button downs or jackets. Pair with jeans for a casual cool look or wear over top of a summer maxi dress to make the most of the changing of seasons. Even sweaters that are simply thinner than your usual winter ones are going to be a good idea. Mine pictured above is from Banana Republic (see it here) and though it seems heavy, it’s actually quite light. Perfect to wear on a 60-degree day!


Avoid an unreasonably cool breeze by throwing a jacket over your favorite transitional fall outfit like a summer dress and sneakers. Whether it’s a jean or leather jacket, or maybe even a rain jacket, your look will probably look that much more complete. After borrowing one of Lexi’s leather jackets for NYFW, I realized that I desperately need my own. BLANKNYC’s Life Changer jacket is no doubt on my wish list. I’m still kicking myself for not buying it during Nordstrom’s anniversary sale, however, when it was just $50. It would go well with so many of my looks this fall and winter!

Boots and booties

Bye-bye sandals! Boots and booties are one of the main reasons why I love fall. They’re easy to style and can make a simple look stand out if you have the right pair. If you don’t already, you should certainly own a pair of riding, over-the-knee, and ankle boots. I wear these ones on an everyday basis during fall, but I think I might buy these ones next. Whatever you do, make sure they’re comfortable. You might want something neutral to match to a number of outfits and become a wardrobe staple.

What are your favorite clothing items to transition from summer to fall in? Let me know in the comments below! Have an amazing rest of the week everyone 🙂

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