Why I'm obsessed with wearing men's clothes
Anderson’s Dior boy, Eminem’s wallet chain and Lebowitz’s sardonicism
This week, I unpack why I shop in the menswear department. For some, it probably starts serendipitously — a borrowed hoodie, a t-shirt never returned, a fleeting moment in a boyfriend’s shirt that suddenly feels better than anything you own. For me though, my long-standing, mildly pathological love for menswear began in childhood and never really left. It’s shaped mostly by tailoring and detail, but remains driven by the crushing humiliation of a shirt busting open at the boobs.
Until next time.
Honestly, no one asked: why I’m obsessed with dressing like a man
Dior | Menswear Summer 2026
Watching Jonathan Anderson’s SS26 menswear collection for Dior this week, I found myself contemplating taking out a personal loan to put myself on the pre-order list. His debut collection delivered a brilliant selection of school sandals, pastel cable knits, silk evening scarves, and embroidered tailored shirts. It had a soft masculine energy that conjured up images of sweet and cheeky Le Labo smelling boys with rosy cheeks fresh-off-the-rugby pitch. Anderson told Vogue he’d thought about boys discovering pieces like those of his collection “in a trunk and just pulling them on.” I can imagine just the man.
As wildly talented as Mr Anderson is, I can’t credit my obsession with menswear entirely to him – if anything, it’s been a preference for as long as I can remember. I just wish I could say my foray into menswear was nearly as chic as Anderson’s Dior boy. At eight years old, it was rare to see me in anything other than knee-length Billabong boardshorts (which I wore religiously until I gained a considerable amount of weight and they quite literally burst at the seams — not chic). Being the early 2000s, no outfit was complete without Globe sneakers and a long silver wallet chain (inspired by Eminem — definitely not chic). My obsession continued through my primary school years, perhaps reaching its crescendo when I wore a tie to the Year 6 casual day at my private all girls school (a test in mental resilience to say the least). My love of menswear seemingly fizzled out in Year 7 when boys entered my world and dressing for the male gaze began to plague my psyche. But that’s an issue for another day.
Details of Anderson’s Dior boy | Dior Menswear Summer 2026
I’ve always shopped in the men’s section (and children’s section too – someone who shops as much as I do doesn’t discriminate). As gender becomes more fluid, and previously strict lines between what was traditionally seen as men’s and women’s clothing begin to fade, I find myself again looking to menswear collections over womens.
While shopping in the men’s section is great, when you’re 5’1’’ it can be difficult to find a blazer that doesn’t look like something your mum bought you to grow into. On the quest for the perfect white shirt, I turned to P. Johnson, known for their impeccably tailored pieces and, amongst other things, made-to-measure shirting. Given that P. Johnson expanded into women's ready-to-wear in 2019, I was annoyed to find this expansion didn’t extend to made-to-measure for women. Any woman who’s experienced a button popping open at the chest knows that custom shirts should be a basic service on offer to women. Perhaps even more so than men (they aren’t liable to be arrested for a stray nipple).
Shirts lead me to cufflinks. Which, unfortunately, are also not commonly found in womenswear. Why must only men’s shirts be fitted with tiny little holes made for detail? Anderson’s Dior boy seemingly adorns his cuffs with tiny ladybirds. Meanwhile, there’s a famine of beauty over here on my shirt cuffs. Perhaps what pains me even more is that most men get lazy and don’t wear cufflinks anyway.
Fran Lebowitz, like most things in my life, understands my pain all too well. The New York icon who’s just as well known for her sartorialism as she is for her sardonicism, once begged the Savile Row tailor Anderson & Sheppard to make her a made-to-measure suit. At first they refused, claiming they didn’t make suits for women and citing the only exception they’d made was a suit for Marlene Dietrich (tough crowd). Thankfully for Lebowitz, and her band of loyalists, Anderson & Sheppard acquiesced and made her one, then several, suits. I had no such luck when I wrote a pleading email to P. Johnson this week — who, for the record, are not tailors on Savile Row and don’t have Marlene Dietrich as a crutch.
Left to right: @mahaliachang Style Editor at GQ | @katfromfinance
The sartorial throng’s most recent obsession with ties has been an easier means of getting back into the menswear momentum. Recently it’s felt like everywhere I look I see incredibly chic women wearing shirts and ties. In this economy, it’s an easy trend to adopt using pieces you (or at least someone you know) may already have in the wardrobe. That being said, I rummaged through my boyfriend’s wardrobe to find two options: a thin black tie seemingly stained with ice cream and a knitted tie in a nauseating shade of green. Hard pass. Luckily, there are a plethora of divine vintage ties available on the likes of eBay, and I snapped up a sexy navy YSL number with fine, tiny gold pinstripes, late last week.
So while no one asked why I’m obsessed with men’s clothes, the answer, I suppose, is simple: sometimes they’re better. Razors, shaving cream, shirts – too often the men’s section offers pieces that are cheaper, better made, and crucially, less concerned with the business of being looked at. There’s something brilliant about stepping into a piece not designed with you in mind, but making it look good anyway. I’m not trying to stage a revolution, I just want a good shirt.
On my mind and in my cart this week:
I’ve been obsessed with New Zealand brands lately and Harris Tapper is no exception. Crafted from structured ivory bonded satin and inspired by ‘60s couture silhouettes, this piece is blatant and utter perfection. Lucky for my bank account, it’s currently sold out.
2. Celine Wool Pin Striped Blazer
In the event you skipped the entire contents of this newsletter and jumped straight to the excellent levels of taste on offer in these recommendations — menswear is on my mind this week! Naturally, therefore, the search for the perfect pinstripe suit is pulsating through my limbic system. This Haider Ackermann for Celine double breasted beauty is excellent (and luckily for me, this Substack essentially goes out into a void each week, so I should have no issues in sharing it).
3. On Self-Respect: Joan Didion
I come back to this essay often, particularly when there’s a lot weighing on my mind. It also serves as the perfect mid-year check-in.
-CCW