Favorite Trends for Early Fall

Holy cow I really can’t believe it’s already October. Chicago had some warm days at the end of September to say goodbye to summer but as a fair-weather girl through and through even I have been totally smitten waking up to 50-degree weather each morning. I have refrained from pulling out my sweaters quite yet I have been really enjoying bringing some darker tones back into my wardrobe. Am I the only person that in the fall and winter my laundry only consists of darks?

So I’m sure you can guess by the title what this post is going to be about. And I’m sure you’re asking “Jessa, why would you do this when you do your weekly Trend Alerts?” Well yes, I will keep doing them but this is a sneak peek at my must-haves for the season and what you should pick up immediately for these cooler nights and warm afternoons.


Pleated skirts and dresses are really big right now. I was looking at dresses for a wedding I have coming up and there were so many dresses with beautiful pleat details. I love how vintage this feels. The pleats have typically been midi length in some kind of chiffon material that moves and flow so beautifully. Pair these skirts with a beautiful pair of booties for my taller ladies or a fun pair of closed-toed heels even sneakers for my little ladies. Add a fitted turtleneck for those colder days and you have the perfect fall look.

Leather Skirts

This is a look I’m definitely excited about, the leather skirt. You want these to be a pencil skirt mostly but I’m here for all the leather. When my mom passed me this vintage pencil skirt a couple of years ago I almost got rid of it but I’m so glad I kept her around because she is absolutely PERFECT to follow this fall trends. Add a pair of booties or a heal and turtle neck again. Or pair with a band t-shirt and a pair of flats, and a trend I would love to try but of course as a petite size couldn’t pull off would be the knee boot with the midi leather skirt. I think I saw the likes of Tezza rocking this look at fashion week in February and I was obsessed.

Knee Boots

Speaking of knee boots this is a trend you need to run to jump on. Last year was all about the over the knee and yes they’re still cool I’m talking the just below the knee boots, or calf hight? I’m still trying to figure out how to search them so I can find my dream pair. These boots can be fitted like 60s style or a little wider like an English riding boot. Personally I’m on the hunt for something in the middle with a slight heel like a pair I had in middle school… sigh one day. But this trend is perfect for pants and a black bodysuit for a night out or with skirts. I would pair mine with something a little more mini to elongate the legs. They are so versatile and I’m sure will carry us into the later fall and winter months.

Felt Hats

Hats… a very polarizing topic and one I will most definitely be covering at some point… But I LOVE a good felt fedora. They are the epitome of fall in my mind. Pair with a dress, jeans, a skirt anything and you have such a chic look. I love that hats are the perfect subtle statement piece and they look great with a cute sweater and a pair of booties for a great cozy look.


My finally early fall must-have is a good basic cardigan. Like I said it’s a bit chilly in the morning and probably getting cooler on your way home from work or school now that it’s getting darker earlier. I carry around outerwear all year long because I’m crazy and always cold but this is a great time of year to pack a basic cardigan in your bag before you leave the house. My go-to cardigans are a chunky knit and hit around the butt so they can go with anything. I have one in grey, black, and cream to match any outfit.

Now that you are armed with these chilly weather essentials get out there head to your local pumpkin patch and do fall right. What is your favorite trend I’ve listed or something that you’re loving instead! Let me know!


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