How to Dress During the Pre-Fall Transition

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Hi, I'm Chelsey

Happy Tuesday! Now that we’re in September, it’s officially time to break out those pre-fall transition pieces. You know, the things that you couldn’t wear during the heatwave known as summer?

Later this week, I’ll talk about my recommended pre-fall transition pieces currently on the shelves to help you shop around. In the meantime, I thought I’d show you how I mixed summer and fall pieces together to create the perfect casual pre-fall transition outfit. I wore the same look in two different color palettes while in New York, and I want to know which outfit is your favorite!

pre-fall transition outfit

Outfit Details:

T-SHIRT(s): Zara | SHORTS 1: Zara | SHORTS 2: STS Blue | SUNGLASSES: Quay Australia

 BOOTS: Steve Madden | SNEAKERS: Nike | PLAID: Red and Yellow both from Nordstrom

In the “pack with me” post, I shared the uncertainty I felt while packing outfits for New York. Not only was it my first time visiting the beautiful city, but they were also in the middle of a very rainy summer. While in New York, the local news reported 51 of the 90 days of summer in New York were filled with rain! Rain often leads to cooler temperatures or extreme humidity, so I decided to pack items that could be layered. If the weather was hot, I had a summer outfit. If the weather dropped to cooler temperatures, I could add a few of the transition pieces to stay warm.

As mentioned earlier, I’ll go into more detail about the transition pieces you need in your wardrobe later this week, but today’s outfit post features two items:

  1. The Cozy Plaid or Flannel
  2. The Short Boot

Style 1: The Daytime Duo with Sneakers

The first look is a bright and comfortable option to wear during the day. I wore it to travel back to Texas and you know what? I would definitely wear it again! The graphic tee says “Style is Never Wrong” and should look a bit familiar to you, as it was featured in my Zara haul video. (If you didn’t know, Zara has the best graphic tees for fashion lovers and/or people with a creative spirit.) I specifically paired it with STS Blue denim shorts because they are a thin and stretchy material. The last thing you want to wear on a flight is a pair of true, stiff denim.

The last day in New York honestly felt like Texas. It was hot and humid! Luckily, we avoided the humidity for the majority of the trip, but the last day had other plans. I say that to say, I would have worn the outfit without the plaid if it wasn’t a travel day because the weather didn’t call for it.

That’s the benefit of styling transition pieces in add-on layer form rather than as a true piece to the outfit: If the weather gets too hot, the transition pieces can be removed without totally disrupting your look!

I ended up keeping the yellow plaid because you never know how cold it may be on the flight. This pre-fall transition look is the perfect option for those of you who aren’t quite ready to get rid of the summer style. You can still rock your light and bright colors, just look for the shades in a long sleeved option! This is my first bright yellow plaid and I was surprised by how much more I liked it over the traditional red style I bought.

They say don’t wear white after Labor Day, but I don’t necessarily believe that. I especially wouldn’t apply it to tennis shoes. I fully intend on wearing my white Nikes through the pre-fall and fall seasons. I wore them for the daytime look because wearing shoes that require socks at the airport is a must. Otherwise, I would have made the outfit even more of a transitional style with a pair of studded boots. (I’ll feature these in an upcoming post, but can we just appreciate the beauty of Chloe’s Susanna boots?! I mean, how rare is it to find black boots with gold detailing!)

pre-fall transition outfit pre-fall transition outfit pre-fall transition outfit

Style 2: The Nighttime Duo with Boots

Funnily enough, the first style was worn on the last day in New York, and this outfit was worn on the first day. The weather was absolutely beautiful but much like LA, NY gets cool at night.

If you’re the opposite of the summer lover, then you probably can’t wait until fall! To quench your thirst for fall fashion while it’s still a little hot in the daytime, incorporate darker shades of summer clothing into your look! I did this by choosing a black graphic tee instead of my usual white selection. The tee reads “Fashion inspires My Life” and much like the first outfit, it is from Zara.

I didn’t pack any jeans for New York because they aren’t the most comfortable to walk around in, so I paired the outfit yet again with stretchy denim shorts from Zara. With the temperature dropping as the sun went down, the transition pieces definitely came in handy. When I wasn’t wearing the red plaid as a mini blanket on the ferry or as a jacket on the walk to the train, I tied it around my waist for convenience.

One thing you definitely can look forward to wearing as we transition to pre-fall and fall is the boot selection! I knew I needed closed-toe shoes in New York after hearing that the bottom of your feet will be black with dirt after walking around all day, so I purchased a pair from Steve Madden right before heading out of town. Luckily, they were comfortable while still having a small 2-3″ heel for a little extra height. Pairing boots with shorts is a combination pretty much reserved for pre-fall transition fashion, so take advantage while you can! Depending on where you live, you may have to swap your shorts for jeans in a few weeks!

pre-fall transition outfit pre-fall transition outfit pre-fall transition outfit

Which pre-fall transition style do you prefer?

Are you still loving all the bright colors that came with summer fashion, or do you prefer the muted fall colors instead? I’m actually a mixture of both! While I love the boots and shorts combination, something about that yellow plaid just calls my name!

Shop pre-fall transition pieces:

Love this post? Check these out:

tips for trying trends and boosting your styleElizabeth and James Nirvana Black Perfume


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