Style According to My Boyfriend

A week or so ago, I asked my sister to give me an outfit challenge, something that would force me to step out of my comfort zone. Without any hesitation or second thought, she challenged me to take my boyfriend's style and make it work for me.

My boyfriend's style consists of 3 main items: a loose, cozy shirt/sweater, running shoes, and straight blue jeans. He usually pulls it all together with a chunky watch, white socks, a black jacket, a messenger bag, and the occasional random scarf. . He is all about comfort. My sister fondly refers to it as 'dad chic'. On the other hand, my style consists of skinny jeans, v-neck tops,  and an array of shoes from heeled ankle boots to pointed ballet flats. Outfits put together to flatter my shape and my height. Running shoes are usually reserved for more athleisure outfits or for actual running and loose tops are never paired with loose bottoms.

So when I initially tried on the loose-fitting, straight boyfriend jeans, running shoes, and my boyfriend's large maroon sweater, I felt a bit frumpy. It was admittedly very comfortable but did nothing for my shape and made me look a tad stumpy. So to adjust the look for my 5'2 frame, I rolled up the hems of my jeans, untucked the sweater, and asked my sister approximately 20 times if I looked alright. Then off we went!

When I sent Joe the first few outfit shots, his reply was: "You look so much better than I do! It's my own style and you STILL pull it off better" MISSION ACCOMPLISHED. 

Who do you think wore it better? 

What outfit should I try next?