How To Transition Your Summer Dresses To Fall

Sep 25, 2017

red off the shoulder dress


Dress: SheIn (c/o) | Jacket: Free People (similar and similar – on sale!) | Handbag: Welden (c/o) | Shoes: Everlane (c/o) 


Hello from Kentucky! If you have been following along we made it to Trevor’s hometown on Saturday and are excited to spend a little time here. I’ll be sharing updates on Instagram and some adorable pics of Zain on the blog soon. As for today, I’m sharing some fun from our recent trip to Portland and how easy it is to keep those summer dresses in your fall wardrobe.

Our trip to Portland came at a great time temperature wise and I was excited to start busting out my fall gear. We actually found the weather to be a lot like Arizona once we landed. I know the city was a bit smoky from the wildfire but it was cool in the morning and evening and pretty hot during the afternoon making layers essential. 

After we landed and checked into our Airbnb, things didn’t go as smoothly as we liked. We realized our place didn’t have AC, my dress for the wedding that had been delayed from being delivered to Chicago was now not being delivered to Portland either and I missed Zain terribly. All of these little inconveniences we obviously not a big deal but they seemed to keep piling on from the day before and that on top of all my mixed emotions about leaving Zain led me to a mini meltdown. 

Trevor wanted to get me out of my funk so he convinced me to walk to the closest pub and sit down for lunch outside. We stumbled upon Chapel Pub, which is a brewery and pub inside a chapel and found the perfect corner seat in the garden. After a good burger, fries and beer I seemed to be in better spirits. Amazing how much fries can do for my well being, right? 

We decided to sneak in a quick nap before we headed downtown to find dinner. I was excited to finally wear this dress that I had bought for the end of my pregnancy. The stretchy material was perfect for my changing body and I thought it paired wonderfully with my faux leather jacket. It’s so easy to transition those favorite summer pieces to fall with just a few tweaks. Throw on a cardigan or moto jacket over your dresses and pair your favorite tops with booties instead of sandals to make everything as versatile as possible. I rounded up some of my favorite moto jackets below that are perfect for this transitional weather and fall! 

With no reservations, we were a little scared as to what we would find to eat. I normally scour reviews, articles and the internet to chose where we eat and make reservations weeks in advance. Unfortunately, life with a newborn seemed to prevent me from ever getting around to that so we were just going with the flow.

Living in Chicago makes it hard to be impressed with food when we visit other cities but we actually had some amazing luck. We stumbled into Lechon and they happened to have an open table for two by the bar. The food ended up being amazingget the empanadas (we ordered them twice) and the grilled octopus! It had been quite some time since Trevor and I had enjoyed a night out and it was lovely to have a glass of wine and spend time chatting with him again. 

After our delicious dinner and banana cream pie dessert we headed over to McMenamins for Jess and Neal’s welcome party. What I thought would be a low key evening turned into us closing the bar down with Kelly and Mitch and having the best time! I can’t tell you how much we needed that night out and I’m so glad I wore this easy and comfy dress. 

Hope you guys are all having a great Monday and make sure to follow along on Instagram for all our Kentucky adventures! 


off the shoulder dress

chicago style blogger

faux leather jacket





welden saddle bag

how to transition your summer dresses to fall




Leave a Reply

Your email address will not be published. Required fields are marked *