AIO to my boyfriend’s (27M) comments on my (29F) appearance?

We’ve been together for a little over a year, long distance but we see each other every week or two for a few days. I’ve only been in one other long term relationship where my ex never made such comments so I’m not sure if I’m not overreacting. Maybe it’s normal. I will only focus on the issue at hand but relationship is healthy otherwise.

Over the course of a year my boyfriend made little comments here and there concerning my appearance. Like seeing a woman on the street and saying that I would “look great in those clothes”, or “I wonder how you would look with similar lashes”, or once I put on a skirt and he flat out said he doesn’t like that skirt. Nothing more extreme.

I recently realised that I don’t like anything in my closet (I started wfh in 2020 and now my clothes look rather frumpy, I mostly wear jeans and a T-shirt or a hoodie), I made a Pinterest board to see what I actually like and showed it to him. He said he loved it. Some time passed and during a totally different conversation he confessed that he doesn’t like the way I dress and he finally feels it’s ok to say it because I’m in the process of refreshing my wardrobe and changing my style. He thought it would motivate me even more to refresh my closet.

I started going to the gym a few months ago (he encouraged me because he “wants us to be healthy as long as possible”) and sometimes he makes motivating comments like “go get that big butt girl” or “you will look fantastic”.

I feel bad about all of his comments for some reason, like I’m not enough and not attractive now the way I am. Instead of motivating me they make me lose motivation. It’s kind of like my boyfriend wants me to be better and look better but all of his comments about it put me off of being better and make me feel inadequate, ugly, and sad. My insecurity is at an all time high while I used to be pretty confident. At the same time I want a partner who will push me and motivate me…

I often see some of my girl friends who completely change their boyfriend’s style and dictate what they wear and for them it’s normal to change a man’s appearance. I don’t know how I feel about it. Even if I dislike some of my boyfriend’s clothes I don’t mention it because it’s clothes he loves, so I want him to happily wear them.

How normal is something like that in a relationship? Am I overreacting? Need a wake up call I’m afraid.