If you’re anything like me, you’ve sabotaged yourself at least once by over-packing. It’s such an easy thing to do: you’ve left packing to the last minute, and rather than plan your outfits, you just toss a bunch of options into your suitcase. This almost always backfires, because the extra choices make it that much harder to pick out outfits each day. And the next thing you know, you’ve bought some souvenirs and you’re suddenly unable to fit everything into your carry-on for the return journey. 

Luckily, I’ve gotten a lot better at the art of packing a carry-on. Last weekend, I headed to Chicago to attend the APAMSA (Asian Pacific American Medical Student Association) National Conference. Since I had four days off for Rosh Hashanah, my mom met me in Chicago for a girls weekend (sorry, Dad!) 

Since I was going to be attending a conference, I had to bring some business professional clothing, but I also needed to bring comfy clothes for traveling and sightseeing. In addition, the forecast reported a mix of cloudy, rainy days and 70 degree sunshine during the time I’d be in Chicago.  

Table of Contents

What I Packed

In total, my trip lasted five days, since I left Friday afternoon and returned Tuesday night. Here’s what I brought with me to Chicago: 

Tops

1. Linen tank top*
2. Purple Blouse
3. White Boyfriend Button Down
4. Striped Button Down
5. White Silk Tank – silk tanks are my favorite thing ever! They’re breathable, go with everything, and take up practically no space in your suitcase! Silk can be pricey, so I usually try to snag them on sale from French Connection and lately have been sewing my own; these tanks from Grana are also pretty affordable at $29! 

Bottoms

1. Black trousers
2. Blue Jeans*

Outerwear

1. Leather Jacket
2. Raincoat
3. Cream Blazer
4. Cropped Trench

Shoes

1. Black Pumps
2. Slip On Sneakers
3. Ankle Boots
4. Lace-up Flats*

Accessories

1. Foldable Tote*
2. Bucket Bag
3. Umbrella
4. Stud Earrings – I love these because they’re both silver and gold, so they’ll go with any other jewelry or accessory hardware! 
5. Scarf

*Indicates that it’s the exact item that I brought with me