Fashion is always changing. Some fashion statements are unique, some are fun and others are unpredictable. Never would I have thought people would be wearing inside-out clothing and calling it fashionable. But here we are in 2026, and this is a reality. 

This new era of fashion begs the question: Are people wearing things like this because it looks good or because it’s new and different? I’d like to go with the second choice, but not everyone would agree with me.

“I really like the look,” Chesky stated. “It’s not just different, but fun and subtle as well. It doesn’t hurt that it’s comfortable as well.”

I will give it to Sam: from the outside, it looks like a cozy sweater. But if the comfy side is on the outside, that means the inside is the real grey outer, making the sweatshirt less comfortable than its original form. 

But if comfort isn’t a factor, I actually do think that the sweatshirt is a good look. Aside from the tag being on the outside (which should be considered a crime), the white background makes the orange letters pop, with the collar and cuffs giving the piece good accents. 

While the idea sounds hip and bump, it’s certainly an odd concept. However, when done right, like in the case of Chesky’s sweatshirt, it can be stylish. But I’d advise exercising caution, as these new sweaters might not always look the part.