I almost forgot why I started this newsletter
Outfit diary, or something like it I guess
I almost didn’t write this.
I kept telling myself the week was boring. Just work and outfits and one cancelled flight. But that wasn’t it. The real reason was that writing about it honestly would mean being vulnerable, and I didn’t want to do that.
The thing is, I started this Substack to process grief. My mom died two years ago. And somewhere along the way I’d started writing around myself instead of about myself. So this week I’m trying the other thing. Outfits and everything underneath them.
I don’t know if it’ll unlock something. We’ll see.
Monday
Sunday was a grief day. The kind that arrives without warning, two years in, when you’ve apparently run out of the allotted time society gives you to be sad about losing your mother. I woke up Monday still carrying it. Instagram seemed pointless. Making a reel seemed pointless. I did it anyway because that’s the thing about routines, they ask nothing of you emotionally, you just show up and they do their thing.
I don’t think it helped this time. But I showed up.
The outfit was navy. All of it. Navy trench coat over a navy textured shirt, navy trousers, croc loafers. The tan bag was the only thing that wasn’t doing the bare minimum. I didn’t choose this look so much as reach for it. When your brain is elsewhere, you dress on instinct, and my instincts apparently go dark and easy and just... navy. It looked more intentional than it felt. That gap between how put-together you look and how you actually are is something I think about a lot.
I did not like how the outfit photographed to be honest. But I like how it felt. Navy, comfort, safety blanket. Funny how and what ends up being a safety blanket, right? What is yours?
Tuesday
Tuesday was Compensation day at work. The day I sit down with each of my direct reports and walk them through their salary, their bonus, their equity, their vesting schedule—their livelihood, basically, in numbers. It’s one of my favorite days of the year because I get to deliver good news to people I think are great. But it is also one of the heaviest. You’re holding someone’s financial reality in your hands and trying to explain it clearly and make them feel seen and valued and you have to get the numbers exactly right because these are not abstract figures, they are rent and savings and plans people have made. I love my team. That’s what makes it so much to carry.
I wanted to feel something different from Monday’s weight. Something with a little more zha zha to it. The result: a ruffle tuxedo shirt—blue and white striped, ruffles down the front—under an oversized navy blazer (still leaning on navy for comfort), with sheer grey trousers and black ballet flats. The trousers are sheer. I wore them to work, to those conversations, and the blazer covered the vibe of it if not the reality, and nobody said a word, and I walked out at the end of the day feeling like I’d gotten away with something small and private and mine.
There’s a specific kind of tired that comes from being responsible for other people. It’s not bad tired. But it’s real. The ruffles help.
Wednesday
By Wednesday my body had collected the entire week’s worth of feeling and simply refused to continue. The Seattle trip I was supposed to go on got cancelled. I took the morning off. I lay there for a while and let myself be tired in a way I hadn’t allowed on Monday or Tuesday.
And then, slowly, I got dressed.
What I wanted—what I actually needed—was space. Room to breathe. The tan oversized blazer. A short that sat low and easy. Croc loafers matched to a croc bag. I’ve started calling this particular energy fuckboy chic—but honestly on Wednesday it was just comfort. Space in my clothes because I had run out of it everywhere else.
I made it to work by noon. The outfit held me together just enough.
Thursday
I woke up Thursday and felt like myself for the first time since Sunday.
I don’t know how else to describe it except that something had shifted. That’s the thing with grief. It’s like a wave. You drown, and then you resurface. I also got my period. All the extra drama of the past week made more sense.
I wore a red tee. Violet grey blazer, cream cargo pants, white sandals, a leather belt bag low. The red tee was the decision. Everyone reaches for safe colours when they’re finding their footing—white, black, grey, things that seem easy. Red seems hard but wow the way it cheered me up. I showed up for myself on Thursday in a way I hadn’t managed since the weekend and the red tee was somehow part of that.
The cargo pants floated when I walked. Wide and easy and cream, and yuuup wore them on a period day coz I am not letting these fears hold back my swagger I JUST got back. The whole outfit had a looseness that felt earned.
Friday
Much lighter!
Good, right? But wait also watch this reel please I edited it during my lunch break on Friday and I Loooove.
That’s the only way I know how to describe Friday—the weight still there but distributed differently, easier to carry. I wore a navy and yellow diagonal stripe rugby shirt, black cropped tights, fringe monk loafers, the tan bag. I had Pilates after work. Awfully convenient to wear the tights all day—built into the look from the start!
The number of compliments I got on that rubgy tee. Honestly it is a good one. I don’t love polos of any kind of myself. But this one works. It has inbuilt style with that drape.
I worked, I went to Pilates, came home. Still tired. But the week was behind me and that felt like an achievement.
So that was last week. I feel a lot better today than I did a week ago. In terms of processing all that, I don’t know if writing this helped yet. Ask me next week.
I’m curious, has getting dressed ever actually helped you through something hard? I’d love to know in the comments. Also, this might be idiotic but I am not mentioning brands and names on purpose. Coz it really isn’t about the items themselves. But also coz I don’t do affiliate links and tbh that really is the most convenient way of linking to things.
But also I am not a gatekeeper. If you really want to know about an item I am wearing, just ask in the comments. Most things are probably Tibi. But just ask, I will answer I promise. <3
Cream pants on day one of your period is bold 💥 that is evidence in itself that you’re stronger than you think!!
I’ve always identified as a “mood dresser” - letting my mood dictate my outfits. But now I’m more of a “field of dreams dresser” - as in build it and they shall come. Some days are really hard, and dressing for the vibes I WANT vs the vibes I’m supplying actually makes a big difference to my mental health.
Wow. Yes to this but also only as much as feels right for you. Thank you for the gift.