My Favorite Fall Wardrobe Transition Pieces

My Favorite Fall Wardrobe Transition Pieces

This past weekend’s mid-60’s temps have gotten me in the mood for everything related to fall – bonfires, spiked apple cider, Halloween, reading a good book in the sunshine without sweating my ass off, and pumpkin flavored/scented everything. (That reminds me, I need to get my Starbucks card loaded and scented candles out ASAP.) I’m not sure how it’s possible, but I think I’m even more excited for fall fashions! I love the freedom of being able to throw on my Birks and head out the door in the heat of summer, but as a thick girl who is perpetually sweaty, I’m ready for weather that warrants wearing more clothes.

Fall always makes me have more intention with what I’m wearing. If I know I’m not going to be miserably hot, I have more freedom to think about what prints and patterns and colors and textures I want to wear instead of focusing mostly on the practicality of an outfit. (See, I’m getting giddy just thinking about it.) I’m especially looking forward to dark/vampy berry tones, fun textures like flannel and corduroy, chunky knits with dark-wash denim, and of course my favorite booties.

I have a feeling it’s going to get warm again before it cools down for good, so for now I’m serving up my favorite transition pieces to help me transition my wardrobe into fall.

Short Taupe Booties

short taupe booties stairs

Taupe suede-ish booties with a low heel are my all-time favorite summer-to-fall shoes. Whether I’m dressing-up a cuffed pair of jeans or dressing-down a satin-y dress, these boots can bring a completely different look to a whole outfit. They’re the perfect neutral and they’re in that Baby Bear sweet spot of inter-seasonal comfort.

Peasant-Style Bell-Sleeve Blouse

Blouses like these are one of the reasons I look forward to fall. They’re longer and a little heavier than the ones I can get away with wearing comfortably in the dead of summer, but when the temp starts to drop a little, these are the first things I break out of my boxes of fall/winter clothes. Plus, the color of this one is everything and I have been so obsessed with embroidery lately. Comfy + cute = happy Kaiti.

peasant sleeve top looking left

Dark-Wash Denim

black denim hand in back pocket

Now, I’m the first to admit that pants suck. Like. I hate (almost) everything about them. But sometimes dresses and skirts and stretchy spandex pants get a little boring – so it’s nice to add a little variety every once in a while. These bad boys from Ava & Viv are specifically tailored to curvy bodies, so they’re a lot more forgiving when you’ve got some junk in the trunk.

Black Jersey Knit T-Shirt Dress

looking right

I have an embarrassing number of black dresses. They’re each a little different in fabric and style, but this one is my #1 gal. She’s soft and flattering and above all, comfy. I don’t know when comfy became a priority in my wardrobe, but I hardly ever wear anything that makes me want to change after a few hours. Dresses like this are so versatile and perfect for almost any occasion!

Denim Jacket

black dress denim jacket black rain booties looking off

As you might recall, I’ve been on the hunt for a good denim jacket for quite some time now. After finding a few that were okay but not superb, I finally found this one on Poshmark and I am in love. It’s perfect for layering and goes with just about every outfit. Especially when it’s a little prickly outside, this jacket is perfect to take for just in case.

Black Rubber Rain Booties

looking down at booties

Speaking of Poshmark, these booties have an interesting story as well. Before I went to college, I bought a pair of tall Hunter rain boots that were supposed to be wide-calf because, well, I have supremely wide calves. They fit kind of okay, but they were a little tight so they made everything below my knee turn into a sauna every time I wore them. Which, during these in-between months is less than pleasant. So, when I found these rain booties, I sold my tall Hunters on Poshmark ASAP. Now I can dance in the rain and not feel like my toes took a vacation to the Amazon rainforest.

Are you ready for fall? Do you have any clothes you wear on repeat when the weather gets a little… unpredictable? Leave a comment and let me know!

black dress denim jacket black rain booties looking at phone

Note: I may receive a small commission if you make a purchase from some of the links in this post. I understand that might make some people uncomfy, but just know all of my opinions always have been and always will be my very own. Like the fact that I think mustard is a government conspiracy to thwart the condiment industry and I AM NOT AMUSED.



  1. Theresa Norton Greco
    September 17, 2017 / 1:14 pm

    I love reading all of your blogs! You have such a talent!!

  2. Sahra
    September 18, 2017 / 10:25 pm

    Love this! I feel like I could liiiiive in tee shirt dresses!

    • September 20, 2017 / 6:12 pm

      SAME girl! Especially this time of year – give me a denim jacket or a flannel and some boots or booties and I’m sold.

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