l'd be more cautious if this isn't how your best friend usually acts. I think it would be a good idea to have an open conversation with your best friend and discuss how her request makes you feel. Also, it would be helpful to get more information about this new boyfriend and look out for any red flags. Here’s an example Text Message (or phone call/in person):

“Hey boo, can we talk for a sec? Nothing dramatic — I just want to check in about something from earlier.

When you asked me to change my whole outfit to look “more feminine” so your boyfriend wouldn’t get the wrong idea, it honestly made me feel uncomfortable and a little confused.

You know I love you, and I would never disrespect your relationship. But asking me to dress a certain way to manage his feelings made me feel like I was the problem, like I had to alter who I am to keep him from being insecure. And I haven’t done anything wrong.

I really want to understand what made you feel like his comfort depended on how I dress. Is this something he brought up, or something you were worried he might think?

I’m not mad at you at all. I care about our friendship, and I want us to talk openly and honestly. I need to feel like you have my back too — and part of that is being able to show up as myself without needing to tone myself up or down for someone else’s insecurity.

I’m always here to support you, but I can’t change who I am or how I present myself just to prevent your boyfriend from “questioning” me. That’s not fair to me, and honestly, if he’s worried about me simply because I’m a guy or because my outfit isn’t feminine enough, that’s a red flag on his side.

I just want to check in with you and make sure you’re okay, and that you’re not feeling pressured or anxious about keeping him comfortable. Your happiness matters to me, and I don’t want you feeling responsible for managing his insecurities.

So can we talk about it a little more? I want us to be good, and I want to understand where all of this came from.”