Gotta love outspoken family members, lol! They get a lot right, and let us know what they see. But sometimes their programming blinds them to certain things, like a son or brother not seeing the sexy. I had to laugh at “feel like I’m in drag” because I know that feeling so well! I’m very comfortable in dresses & skirts, but there are some items that feel forced in just that way.
When I think “supervisor at the dock”, I think chunky and blocky throughout. Then I look at this pic and your midsection is clearly not that. The vibe I get is similar to women wearing men’s jeans, where the curves & softness just can’t be denied, ifykwim.
The shoulders of the blazer do fit you well and you have strong shoulders. That’s what I like (Bruno Mars stuck in my head, but I do like that part of this).
You know your colors so well, and tossing in the red boots is your signature color play.
So even though I can’t say what to do instead, I think the problem is the pants. Short pants generally are tricky, and I think it’s great that you, a tall woman, are willing to give them a go. But from the hips down, I don’t think these do anything for you. There is no hint of body structure or the shape of your legs in them. Not saying you have to go with skinnies—soft & flowing that fits just right can also reveal structure.
So cool that you are willing to share when you don’t quite nail it!
ETA: I don’t mean give up on the pants altogether, just that I don’t think they work with this ensemble. In another outfit, the might be great.