This was a proper country op shop, with old-fashioned prices – the lambswool/angora jumper, stretch miniskirt, Glomesh wallet, glitter shoelaces and leather shoes cost me a grand total of $12. You can probably also tell that it's Seven Sisters Spring! (A trans-seasonal period that's not too hot and not too cold.)
And it's the class dimensions of this look that I find quite confronting. Even though they were only $5, I really angsted over whether to buy the boat shoes. When I was at school and uni, boat shoes were the uniform of private-school louts, along with rugby shirts and chino pants. I associate them with the sexism and political conservatism that come with being complacent about gender and class privilege.
But in recent years I've noticed that cool young people are wearing chinos (albeit skinny-legged rather than the pleated, baggy sort popular in the '90s), boat shoes, and chambray shirts (often worn buttoned to the neck). It's as if they are reinscribing these garments' connotations of wealth as aspirational and glamorous, similarly to the way 'Ivy Style' and 'prep' are nostalgic for a vanished WASP elite.
Recently I read an eye-opening Tatler feature about the Scottish aristocracy (reading Tatler always sends me into a tailspin of "who even are these people?") and thought to myself, this is the culture that produced my beloved British Country Winter aesthetic. What do I love about this look? If I'm being honest, it is that it's an elite look, one that speaks of the low-key luxury and leisure that intergenerational wealth can enable.
Boat shoes (also known as deck shoes or top-siders) are intended to be worn for leisure boating, as their name implies. (Interestingly, John Sipe, the innovator of cutting grooves in the rubber tread of tyres to increase their traction in slippery conditions, is frequently said to have cut lines in his own shoes while working in a slaughterhouse – hardly an elite occupation.)
The recognisable style – sturdily stitched leather; deep-treaded rubber soles; moccasin-style top-seamed toe; leather laces threaded through eyelets – was invented in 1935 by avid boater Paul Sperry, who called them the Sperry Top-Sider. They took off in 1939 when the US Navy decided to make them standard issue for sailors.
Traditionally they are never worn with socks. Because of the historical association of leisure boating with the monied US north-east, who also sent their sons to Ivy League colleges, a practical item became a signifier of privilege.
But as Jessica Friedmann commented on my Instagram, "There's definitely a class connotation but I like the idea of 'casual' shoes that are as meticulously and carefully made as dress shoes, to be chucked on with jeans on the weekend. It's one of the 'old money' affectations that I like - investing on good quality no matter the situation."
And she's right. There's something alluring about the zero-fucks way that old-money people buy expensive, beautifully made clothes and then just wear the shit out of them. That, I think, is why the modern Ivy/prep style revival can look too fussy and overdressed compared to the carefree fratboys captured in Take Ivy.
This aesthetic also challenges me because it is a conservative style. Fashion – by which I mean the industrial cycle of trends – recognises and rewards innovation and eccentricity, which is why older women are celebrated when they dress boldly and individually, and dismissed as 'frumpy' when they stick to unshowy, utilitarian 'classics'.
Young people can potentially make conservative clothes fashionable, due to the incongruity of fresh-faced, taut-bodied beauties wearing otherwise 'ugly' and 'unflattering' clothes. Hence the popularity (ironic or unironic) of 'normcore' and the 'Elaine from Seinfeld' look. But if you are 'plain', fat, or once you get over a certain age-related event horizon (which I constantly fret I have done), you have two options.
First is to dress flamboyantly and eccentrically in order to 'read' as youthful, beautiful and stylish. (This was Diana Vreeland's sartorial philosophy.) Second is to embrace minimalism: a cerebral and challenging 'fashionability' that flatters the non-normatively beautiful because it radically de-emphasises the body and focuses on the textural and sculptural qualities of the materials. (Coco Chanel was a prototypical minimalist.)
So, to return to items such as these boat shoes, I have this paranoid conviction that I can only 'get away with' them if I don't wear them with other 'preppy' items. Here they are today, on their first spin under my ownership:
I chose the skirt to match the shoes, and decided not to emphasise the black in the skirt, so I chose a white top with stripes of similar thickness, to highlight the block colours rather than the blackness of the stripes. I also wore my denim jacket because it added both colour and casualness to the outfit, and because blue denim is inextricable from Seven Sisters Summer in my mind.
I don't think long skirts are the go with these shoes; the effect is daggy. I feel like they go best with pants. (I don't wear jeans or shorts.) But perhaps I could also wear them with simple, non-uber-femme dresses, with miniskirts and leggings (I exposed my naked thighs to the world once – as documented in Out of Shape – and am never doing it again), or with knee-length pencil skirts.
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