Thanks for this really lovely post.
I did this freelance for a while in the early 2000's but didn't manage to take off because I wasn't the greatest at social media back then and social media wasn't the greatest back then, but for the time I did it I loved it. I was nowhere in the league of someone like your stylist who sounds lovely. I charged a lot less because I was working my way up while working another job entirely. I loved talking to a new client, hearing what they said beneath what they were telling me. And it is about getting people outside of what they think their comfort zone is but not in a "You will be zany!" no one who goes to a personal stylist really wants that and if they did they'd figure it out for themselves. People tend not to feel right in what they're wearing, but they want to be comfortable and they're worried that if they go too far outside their comfort zone, etc. You take them as far as you know they want to go, which generally isn't too far but includes different colours, patterns, you look at them, you just try to see them and then you start to build up what you think will work. The things they don't like as important as what they do like. And you teach yourself as you go alone. I was constantly looking at people in the street, magazines. Who really suited what, what did I think of that shirt with those trousers, etc. God, I loved it. I love fashion, style, I love it when someone looks their absolute best and it's because you were able to say to them, hey you look great, but I think that x would look so good with it. And it does and you've made someone's day.
And it is all about learning to love who you are not who you might be a year down the line if you just don't eat that and you just do this exercise. Of course, it's different strokes and if someone wants to diet and then change their style I'm all for it because it's what makes each of us happy. But I LOVE that a new style can make you look so fabulous that the fact that you're not happy at a size [whatever that might be] you suddenly realise that you are in fact lovely just as you are and it was that baggy old shapeless thing that was making you feel bad.
I still have some mad online and card-based "databases" of when I'd happily spend hours going through new season stuff and figure out what to look for when the new season reached the high street. I was such a geek for that "job". Reading about your experience has made me feel some of the pleasure I got from it, so thank you and I'm delighted for you that it's made you so happy.
Fwiw, people saying they like the clothes you've chosen/think they're boring/think that's a lot of money to spend on something not very exciting, don't get it. First we all know that what something looks like in a photo compared to what it does when it's on are two different things. I see that blue dress on you (from the photo you showed of you in the shirt and trousers) and yes, I get it. Yes, it's expensive but I think if some of us looked at how much we spent on clothes that we end up hating/never really liked/never really wear over the course of a year we'd be horrified at how much it was. Mine wouldn't get to that amount simply because I don't have that much money, but I know I've spent hundreds on fast fashion in the past to fill some sort of hole! Also, price per wear. Better quality, looks better, enjoy wearing, more wear, because a lot of those pieces you've bought will last seasons because they're more classic and you're not looking for a "fashion fix". Different accessories, etc. You'll buy a bit less some seasons and not be wasting money. Also who gives a shit what other people think is "boring"?! I'm currently seriously ill and I've decided that most of the time I'm dressing every which way. I had an unusual event yesterday and wore a red sequined long dress, shoulder pads, backless, glorious sleeves. I wore it with a mantilla and black paper roses in my hair for a while and then changed to a slightly sparkly red turbon for the for rest of the say. Over the top jewellery, green eye crayon. Would I recommend that to someone who wanted to feel a spring in their step on the school run? Of course. Not!
Sorry, I'm waffling. I love that you're happy, that I know you look great and that you've been able to afford to do this for yourself with a woman who is clearly bringing a lot of joy into the lives of other women. Long may you stay happy and thank you for bringing back lovely memories to me.