09/26/2012 08:16 am ET Updated Nov 26, 2012

Fall Fashion: How My Recent Trip To Chicago Got Me Excited For Sweaters, Scarves, Boots And Jackets (PHOTOS)

In New York City, the weather seems to change from the peak of summer to depths of winter in the blink of an eye, leaving only a few days for true autumnal fashion in between. While I am excited to abandon my shorts, tank tops and frequent grooming habits soon, I have to admit: I am not quite ready to transition summer clothes to fall, or really, to face the end of summertime.

On a trip to Chicago this past weekend, however, I was forced to fast-forward to fall. Keep this picture in mind: On the day that I left New York, I was wearing a cotton mini dress and sandals. This look was entirely appropriate for the near-80 degree temperature at home, but upon arriving in Chicago, I was suddenly glad I had heeded the advice of the friends I was visiting. I immediately added a trench coat and wool scarf to my look, two items I haven't worn since mid-April, and became worried about what I had packed.

Although I knew logically that it was colder in Chicago than in New York, I wasn't ready to commit to fall fashion when I was packing. Instead, I tried to compromise: I brought one pair of jeans, one pair of high-heeled boots, a trench and a sweater. The rest of my suitcase was filled with sandals, mini-skirts, silk dresses and tank tops -- basically everything that I have loved wearing this summer.

Let me just say: none of these warm-weather pieces were wearable over the weekend. They were just along for the trip and never made it out of the suitcase. Fortunately, the one pair of black high-waisted skinny jeans that I brought are perhaps the most versatile item in my wardrobe. I could pair them with a tank top and my jacket and I would be good to go. But, this did mean I would have to wear them for four days in a row. (It was a much-needed long weekend.) My footwear presented another problem: The brown heeled sandals I had worn on the plane were not going to fly for a cold, rainy day and the same went for the pair of flat black sandals I brought in my bag. So, 4-inch-tall black heeled boots it was. For the whole weekend, which included a trip to a farmer's market in the park, a walk down Michigan Avenue and several nights of dancing. (Hey, it was vacation!)

Essentially, I had one outfit for the weekend: black boots, black jeans, trench and a scarf. The only variables were my underwear and t-shirt.

Upon landing back in New York, I was faced with the harsh reality that my temporary uniform was no longer weather-appropriate. I was hot in my jacket and scarf and stuffed them in my already overly-full suitcase for the subway ride from the airport. On the short walk from the station to my apartment, I disrobed again, pulling off my cashmere sweater and tying it around my waist in true '90s style. The truth was, while it was already fall in Chicago, it was still summer in New York. But, my four days in the Midwest had prepared me for autumn. I was ready! I had envisioned the cute sweater-blazer combinations I could wear when finally reunited with my full wardrobe. I was yearning for pants, scarves and boots, but the weather wasn't quite as ready as I was.

So, I've reached a sort of 70 degree compromise by mixing and matching summer and fall pieces. Today, I wore a sweater over a tank top with a high waisted skirt, and tomorrow I'll pair a jacket with a summer dress, but now I can't wait for the days where I will be able to dress fully for fall.

Want more? Take a peek at the photos below to see our favorite fall 2012 trends and be sure to check out Stylelist on Twitter, Facebook, Tumblr and Pinterest.

Fall 2012 Trend Report