Whenever I travel to a new city, there’s always one thing I think about ahead of time: what am I actually going to wear?
Chicago in the fall makes that question especially tricky. I want to capture great street-style photos, but I also don’t want to pack an entire suitcase just for outfits. So this time, when I prepared for my trip, I didn’t simply look for fashionable pieces. I wanted every item I packed to be something I could genuinely wear throughout the day.
While browsing VIPOutlet, I was surprised by the variety of fall clothing and footwear available. I ended up choosing four pieces that together created what I consider my ideal Chicago autumn travel wardrobe.
01 | The North Face Apex Bionic 3 Jacket: I Want a Jacket That Can Handle City Weather
The first thing that caught my attention was the The North Face Apex Bionic 3 Jacket. One thing I dislike most when traveling is realizing I dressed incorrectly after the weather suddenly changes. In fall, I might leave my hotel in the morning thinking the temperature feels perfect, only to find myself getting cold later in the afternoon.
This jacket feels well suited to that kind of city travel. It features WindWall technology and is designed to provide wind resistance, making it a practical option for cooler and damp conditions. I particularly like its understated appearance. I also came across it through VIPOutlet, which made it an interesting option to consider when looking for practical travel clothing without overcomplicating my packing.
I can wear it with a sweater and jeans, or simply layer it over a basic long-sleeve top. For me, a travel jacket shouldn’t dominate the entire outfit. It should make me feel comfortable enough to head outside without constantly thinking about the weather.
If I’m walking from Millennium Park toward the Chicago River, I’d much rather be thinking about where to find my next coffee shop than wondering whether I need to go back to the hotel and change.
02 | Carhartt Women’s Loose Fit Fleece Coat: I Want a Softer Feel for Fall
The second piece I chose is the Carhartt Women’s Loose Fit Fleece Coat. If the first jacket is mainly about dealing with changing weather, this one is more about how I want my fall outfits to feel.
I really enjoy wearing soft fabrics in autumn. Especially when I’m traveling, I might be walking for hours, so I want my clothes to have some visual layering without feeling restrictive.
This Carhartt fleece coat uses soft polyester fleece and has a relatively loose fit. I came across this piece through VIPOutlet, which is also a convenient place to browse for practical everyday clothing when putting together a travel wardrobe. I would pair it with a simple white top, straight-leg jeans, and sneakers. What I like most is how effortless the combination feels.
When I travel, I don’t necessarily want a completely different style every day. I prefer bringing a few basic pieces that work well together, so I don’t have to spend too much time standing in front of the mirror every morning. For me, this Carhartt coat is my “comfort piece.” When I’ve been walking for hours and the temperature starts dropping, I know I’ll be glad I packed it.
03 | Brooks Adrenaline GTS 24: I Finally Accept That Travel Shoes Should Be Comfortable First
I used to make a very typical travel mistake: I would bring a pair of shoes because they looked good in photos, even though they weren’t actually suitable for walking all day.By the second day of the trip, I would regret it.
So when I saw the Brooks Adrenaline GTS 24 Running Shoes, I paid much more attention than I normally would.The Brooks Adrenaline GTS 24 features the GuideRails support system and cushioning designed for everyday movement. For a city trip that involves a lot of walking, I find that especially practical.
My reason for liking them is actually very simple: Chicago isn’t a city where I want to spend the entire day sitting still.I might spend the morning walking around a museum, head toward the lake in the afternoon, and then look for a restaurant in the evening. If my feet are exhausted by the end of the day, even the best outfit won’t make me happy.
Now I prefer to put comfort first and use my pants, jacket, and accessories to complete the overall look.For me, the best travel shoes are the ones that let me forget I’m even wearing them.
04 | Sorel Evie II Lace Wedge Booties: I Still Want a Little Sophistication
The final piece I chose is the Sorel Evie II Lace Wedge Booties.Although I’ve decided that comfort should come first when I travel, I still don’t want to wear sneakers every single day.
Especially in the evening, if I’m going out for dinner or want to take some photos with a stronger autumn atmosphere, I still want my outfit to feel a little more polished.These Sorel booties feature a waterproof suede upper and lace-up design.I really like the way they look with trousers, knitwear, and a long coat.
I can already imagine walking through Chicago in the early evening, when the temperature starts to drop and the streetlights gradually come on. At that moment, I think an autumn-inspired pair of boots fits the atmosphere much better than sneakers.I probably won’t wear them every day, but that’s exactly why I think they deserve a place in my suitcase.
I No Longer Pack Half My Wardrobe for an Autumn Trip to Chicago
When I packed for my Chicago trip, I noticed that I was much more selective than I used to be. The North Face Apex Bionic 3 Jacket became my choice for changing weather, while the Carhartt fleece coat gave me a soft and comfortable layer for everyday outfits. The Brooks Adrenaline GTS 24 made long walks around the city easier, and the Sorel Evie II Lace Wedge Booties added a more polished touch to my evening looks.
One thing I really liked about VIPOutlet was being able to browse different brands and types of clothing and footwear in one place. Instead of choosing items simply because they looked good, I could think about how each piece would actually fit into the way I travel. I no longer wanted to pack a huge amount of clothing just to feel prepared.
I would rather bring one jacket that works with several outfits, one pair of shoes that can handle hours of walking, and one comfortable fleece layer that I can wear from morning to evening. After preparing my Chicago trip through VIPOutlet, I realized that my travel outfits don’t have to look completely different every day.
For me, the right travel clothes are simply the ones that make me want to leave the hotel, keep exploring, and stop along the way to take photos. This time, I want my Chicago autumn to feel a little simpler and more comfortable, while still reflecting my own style.
