Get Ready with Me for a Two Weeks Business Trip

For all of us working girls going on business trips to the client-side, it can be a challenge to pack outfits for an extended period of time. So read along to see what I decided to bring with me on a two weeks trip to Chicago in March.

Get Ready With Me

Before even starting to look in my closet or in shops, I took a peek at the weather in that period. The results weren’t that great, so the Windy City is really owning up to its name, therefore I had to go towards winter clothes that prevent me from freezing in the 10 to 15 minutes that will take me to go from the hotel to the office and back.

Another thing I took into consideration is the limited amount of luggage that I want to bring, caring a huge suitcase through the city’s crowded streets is not fun. With that being said, I had to be able to reconfigure the outfits as much as possible.

Being a shoe addict it was easier for me to start with the bottom, I want to bring only one pair to ankle boots that are both comfy and stylish, and go very well with my wool coat. Both of those will be the foundation for all of my other outfits.

Given the fact that I work in the IT sector, I don’t have a strict dress code, but I do like to be in the smart casual area. Most of the time, I like to keep Friday as a casual day, where I add the regular blue jeans and a loose shirt. Since I will be carrying my laptop bag with me, I will not add another purse, one item less for me to worry about.

So here are my peaks for the 10 days in the office:

  • Two dresses that are comfy and look good, alongside with them would be a pair of very dense stockings


  • A long shirt that can act like a dress and an oversized cashmere cape/sweater combined with black leggings



  • Suite pants with elegant shirts 


  • Casual shirts with classic black jeans


  • Oversized polka dots shirt and a classic black shirt with blue jeans


  • Classic light brown wool coat with a matching scarf


Even though the dress code would allow me to wear the urban/street style I prefer to take the opportunity and dress up a little bit, keeping in mind that I don’t want to stand out too much, that being the reason I like to keep the colors neutral. Another thing that I like to do is to have in mind when I will wear then, this way I will not waste any time in the morning, that this is the reason you see the outfits in pairs, Monday will be for dresses, Tuesday for leggings and so on.

I hope you enjoyed the outfits and will make your life easier when it comes to packing your bags for a client visit. Stay warm everybody!

One thought on “Get Ready with Me for a Two Weeks Business Trip

  1. Pingback: Last Month’s Favorites: February 2019 – Bitter Sweet

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