A soft soundtrack for your Sunday reading: Sweet Symphony by Joy Oladokun.
If you’re new here, I’m an outfit repeater. My seasonal lookbook tends to include no more than seven outfits. After years of navigating a bloated wardrobe and some trial and error, I found that this number covers all my bases (work, social events, etc.). I think outfit planning equals outfit satisfaction, so I dedicate an evening to styling these outfits early in the season. It takes the second-guessing and decision fatigue out of getting dressed for a few months. More importantly, I dress more like myself than I ever have.
It’s been a while since I shared my seven outfits, and my life looks a lot different than when I last did. Curating my wardrobe for the winter, I had to consider that I’m out and about more than I used to. I now rarely work from home and meet friends in the evenings more often. I’m single after separating from my partner of a decade four months ago, and as of recently, I’m officially dating.
I was apprehensive about how dating would impact my relationship with my wardrobe. The single years of my twenties were when I felt most untethered to my style, as I dressed purely for the male gaze. I remember taking the Central line to Oxford Circus after work several nights a week to buy a new tight dress to walk past my work crush’s desk the next day. I massively overspent on clothes in those days.
I started having short-lived, casual hook-ups quickly after becoming single (a month later), but I was petrified of going on an actual date. I did what my therapist calls ‘leading with sex, as a way to deflect from my insecurities’. Being naked with someone didn’t feel scary, and having (safe!) sex and pillow talk with near strangers came naturally. The thought of sitting opposite someone in a pub, with nothing in the way of their judgement and without a drink to take the edge off (I have a very low tolerance to alcohol, so I prefer not to drink on a first date), paralysed me with fear. I was sure they would find me vapid and uninteresting. I remember reading
’s newsletters recounting her first date and the first time she had sex post-divorce. Of her first date, she writes, ‘In the cab on the way to the bar, I blacked out and resuscitated myself a dozen times’. I found it fiercely relatable, and it made me howl with laughter. I had a hypnotherapy session to address my fear of dating, and it worked a miracle like with everything I had recourse to hypnotherapy for. [If you’re in London, I see Zoë Clews].The barometer for whether I’m hanging out with the right person is the same as in my twenties: how much do I feel the need to change myself to feel attractive to them? When I get ready to meet them, do I happily reach for my usual outfits and feel good about it? Or do I feel compelled to shop for more worthy clothes or even a brand-new style? This goes way beyond my wardrobe. I openly admit to not feeling very whole at this point in my life. I’m having to remember which choices I made for myself versus the ones I made for the relationship. I have to re-learn what I like and dislike or how I want to spend my free time. Dating increases the stakes. With some men, I find myself lacking, like I should have been watching more movies, listening to cooler music, partaking in more creative pursuits, etc. With others, I love who I am.
Post-breakup, I repainted the walls of my apartment a calming vanilla white and got rid of every last piece of furniture. Just as I finished redecorating, I started a fling with a guy who worked with antique furniture. I was in awe of his job and taste level, and it made me hate the mass-produced pieces I had spent hours lovingly selecting for my new interior - I found them tacky and distasteful. He was kind and non-judgmental; these feelings were entirely self-inflicted. My therapist says that as I rediscover myself, I seem to be trying on these men's personas as one would try on a new coat for size and fit. The day we stopped hanging out, I loved my new apartment again.
The internet depicts being single and modern dating as a gender-antagonising hellscape. I may be new to it, but I’ve been having the time of my life. Going on a date still makes me nervous, but it brings out a side of me that I lost a long time ago. I’m finding that men in their late thirties don’t shy away from emotional depth. I’m having intellectually stimulating conversations. I’m grateful for the opportunity to connect with new people from different walks of life. My Gemini curiosity is being satiated. I grew up in a very paternalistic family unit and did not have an example of healthy masculinity until well into adulthood. I have always rejected my masculine energy, never had any interest in friendships with men, and always seen them as other. Dating has done more to heal my relationship with the other gender than I expected. I have made friends amongst those with whom there was no romantic spark.
Shortly after I became single, I discovered Jillian Turecki’s podcast. It’s helped me develop a healthy approach to dating despite my self-doubt and anxious-leaning attachment style. Whether you’re single or in a relationship, it's a really good resource.
On one of these dates, I met someone whose aura instantly felt like warm honey to my nervous system. He is very different from anyone I have ever met. We hang out often. We laugh a lot. We hold each other extra tight. Something is going on here. I will keep you posted.
My Everyday Uniform (1/7)
To work from and outside of the house, run errands, and nights in with my girlfriends.
This Seven Look Season framework isn’t rigid. Seven is the number that works for the season of life I’m in. You may need less or slightly more. I wear some combination of the outfits you see here most of the time. I also own multiples of the basic pieces and a few other go-to tops I resort to when I’m behind on laundry.
This first outfit, or a slight variation of it, is what I wear seventy per cent of the time. It’s my second skin. This outfit is me.
Those who have followed my personal style journey will notice I veer more and more minimalistic each season. This surprises me too, but it is what feels most authentic. It’s a simple outfit made of intentional pieces (I have a newsletter about how to create impactful casual outfits coming up). Each piece is oversized on my frame, just how I like them to be, and the accessories (boat shoes, scarf, and vintage bag) subtly communicate my style identity.
I’ve recently started wearing a sports bra under my everyday clothes, and I don’t think I’m ever going back. Compared to the underwired full-cup bras I’m accustomed to, I like their comfort and minimising effect. I like this one for everyday high support and this one for roaming around the house.
My First Date Look (2/7)
For first dates, pub nights with friends, and work lunches.
This jacket was a present to myself when I broke up with my ex. I had wanted a fringe jacket for years, and this became the first big purchase I ever made on a whim. It was the perfect timing. Every time I put it on it will be a reminder that I chose happiness. It also looks insanely good.
I wanted a go-to outfit for first dates so nothing would add to the stress of it. There is no piece of clothing in my closet that I cherish more than my Studio Nicholson Chalco pants, so they had to be a part of it. They are extremely wide, with a dropped crotch, and tell a story of how I like to dress: a little boyish. They’re as far from conventionally flattering as trousers get. That felt right. Firstly, because I feel sexier in oversized clothes. Secondly, because I want to show up authentically. If they like a hyper-feminine style, they know they won’t get that from me from the start. The jacket complemented the pants perfectly. It’s short, so I wear it as a top. Both pieces have a lot of character, but I feel entirely myself and comfortable in them. When I posted a photo of this look on Substack Notes, someone in the comments summed it up better than I could: ‘casual, with your own personality stamped on it’.
When I know I will be taking my clothes off in front of someone for the first time, I wear this thong and bralette set. On the one hand, it’s sexy, flattering, comfortable, and invisible under clothes; on the other, it feels less pompous than my lace-y underwear. I’m usually a 32F bra size and wear a Medium.
Two Evening Looks (3/7 and 4/7)
To go out for dinner and drinks with my girlfriends and for fancier work events.
You’ve asked to see how I style this top. How I style it is probably not how the designer intended it. Something about going out tops feels stuck in the early aughts for me. I like their polish to be broken down and messed with a little. The big trousers make the top look modern and more me.
Also, my love for this Anderson’s belt knows no bounds. It’s great value, and I have every intention of buying it in every colour.
I was surprised by how many guys noticed that the pants I wore on our date were the same ones I wore in one of my Hinge pictures. I’m also consistently surprised by how many of these men - at least the ones I choose to date - care about fAsHiOn. They pay a lot of attention to how they dress and say they appreciate it when a romantic partner has a strong style identity. I definitely do not remember that being the case in my twenties.
A friend, who is now happily married, reminded me that she used to come to me for advice on what to wear on dates. The inexperienced leading the inexperienced, ha! Apparently, I would recommend that she wear the clothes she’d wear in her day-to-day life. When it comes to hair and makeup, now that I’m in her shoes, I’m definitely not following my own advice; I spend two hours making my hair and makeup look as flawlessly natural as can be. Yikes. When it comes to clothes, I do stick to what feels most me and most comfortable. I save my fussier pieces, like these tops, for evenings out with my girls.
Another Daytime Casual Look (5/7)
To work from and outside of the house, run errands, and nights in with my girlfriends.
Wearing loungewear or ‘house clothes’ to work from home never did anything for my mental health and motivation. I feel much better in outfits like this one that don’t compromise on comfort but still make me feel like my best self to work, write, and create every day.
Two Day-to-Night Versatile Looks (6/7 and 7/7)
For workdays that end in a dinner with friends or a second or third date.
This look is more classic and cutesy than what I usually like to wear, but something about it makes me feel… limber. Like I want to get up and dance. I have worn it on dates (hat included) and felt great. It just goes to show personal style is flexible.
Reformation takes the cake for the most hit-and-miss brand out there. I have seen them come out with the most appalling quality. However, I LOVE my Reformation cashmere pieces. The Clara cardigan (which I always wear back to front for some reason) and the Dana crewneck are some of the most worn pieces in my closet. They are lightweight but warm. They don’t pill much (although pilling is not always a sign of poor quality). Best of all, they come out unscathed from my washing machine’s wool cycle, which allows me to keep them on high rotation. Again, beware, as even within the cashmere range, not all pieces are created equal; wanting to expand my collection, I tried on the Boyfriend cashmere sweater this week and found it terrible (it’s shapeless and too thin).
One of you recently asked what item I have held in my wardrobe the longest. It’s this Isabel Marant denim jacket my mum gifted me when I was in my last year of high school. I keep finding new ways to style it. It’s a true year-rounder. It’s also the piece I have worn to every gig I have been to for close to two decades.
I read this as if I were single again too, in need of wardrobe solace to start dating again!!! I'm kinda sad I'm not lol. Love you're enjoying dating so much and that it's going so well (you SO deserve it) but really with you every one of your outfits is a lucky one cause they're just so perfect.
I ate this piece up. Love reading about your life and then seeing it illustrated through style. Adore what you currently have in rotation. Thank you for sharing with us!