Good friends lift you up, inspire, and push you to do your best, but best friends know your weaknesses, and are able to zero in on your insecurities with laser-like precision. This is not always a bad thing—as it’s important to remain humble—but if you are trying out a new “look,” such as a jaunty hat or brightly coloured lip, it’s best to take it for a spin away from your friends (who might have opinions).
Even if your friends aren’t arseholes, they will feel compelled to comment on whatever aspect of your appearance you have altered, and it’s best to try out a bold new look away from their gaze, so you don’t internalize their reactions before you have a feel for the piece. (Men will claim they do not do this, but when I worked in engineering—which was a very dude-heavy environment—I could not wear a pale pink lipstick without an “Oooh looks like someone dressed up today!” being uttered in my direction.)
It’s a particularly helpful strategy if you are stepping outside of your comfort zone. I, for instance, am not a hat person, and the sudden donning of a hat is going to elicit comments from my friends no matter what I do, so I have to have my opinion fully formed before going in. You know what they (sports people?) say: The best defence is a good offence, and the only good offence here is confidence.
The first time I dyed my hair blue, I immediately went to a bar that I knew would be devoid of friends and acquaintances. I drank my martini and got comfortable existing as a woman with blue hair. Not only did no one comment, but a man offered to buy me a drink (I declined). After finishing the drink I had bought myself, I went to my usual bar that is staffed entirely with my friends, and was greeted with “What did you do to your hair?” “I dyed it blue,” I said, steeled by my earlier interactions (and lack of reactions).
But even without the positive reinforcement of someone hitting on you, trying a look out alone allows one to get a handle on how the accessory or cosmetic makes them feel. This is how I learned that I am not a beret girl. I have tried to casually wear a beret out in the world three times, and each time I feel like I’m wearing a costume, even though no one is reacting poorly to it. Every time I put the bright red wool hat on top of my skull, I am distracted by the fact that it is there, pulling eyes onto my very round head. This is not ideal. (Sometimes I wear the beret on vacation, because it’s fun to not feel like oneself on vacation.)
Berets aside, this move has let me explore several bold items such as oddly-shaped sunglasses, Cheeto-branded bodysuits, very dark lipstick, extremely winged liner, and a wide array of plunging necklines, and I wear them all with confidence. (Actually, I rarely test out the necklines anymore; I’m very comfortable with the reactions they elicit.)