First off, thank you to Katie for the hat.

Now, let’s talk about my impeccable sense of style…

When I am an old woman I shall wear purple
With a red hat that doesn’t go, and doesn’t suit me,
And I shall spend my pension
on brandy and summer gloves
And satin sandals,
and say we’ve no money for butter.

— Jenny Joseph

In my early 20s, I discovered a great hack for getting away with being an alcoholic in London: Don’t dress like a drunk.

Back in those days, if you saw me staggering out of a nightclub or into a pub, chances are I’d be wearing a dress shirt with french cuffs, probably with a jacket. Possibly a cashmere sweater. But never, ever a t-shirt.

Understand, this had absolutely nothing to do with vanity, or style (I had plenty of the former but none of the latter) but rather it was a question of practicality. As readers of The Upgrade will know, back in those days I was something of a master of “blagging”: That is, talking my way into fancy parties or night clubs or conferences in order to score free booze and other entertainment. I also liked to hang out in members clubs, and other places where rich and important people could be found.

One thing I figured out very early: A blagger can be a drunk, or he can be dressed like a drunk, but never both.  I lost count of the number of times that I was whisked through a velvet rope with a story about a lost invite, or some very important message I had to deliver to a VIP, while my far more sober (but t-shirt clad) counterparts were left behind in the cold. A drunk man walking though a hotel lobby in a suit is far less jarring to a doorman’s eye than is a sober man in torn jeans. (This, by the way, is why I continued to carry a Blackberry long after everyone else moved to iPhones. I mean he seems jobless and wasted but he’s on a Blackberry…)

When I got sober, and stopped living in hotels, I also stopped spending money on clothes. Instead, every few months, I would trudge to H&M (the sartorial equivalent of a UN food bank) and fill a basket with the cheapest, blandest t-shirts and hoodies I could find. I no longer had to disguise myself as a functioning adult, so I fell easily into the uniform of Silicon Valley.

The great thing about shitty clothes that don’t really fit is that even if you start to put on weight (as I did when I moved to Vegas), they still don’t really fit. A hoodie hides a multitude of dinners.

Fast forward to present day. Or specifically to the start of last year, by which time my closet (actually, a couple of drawers) was entirely engineered for comfort. I hadn’t realized quite how out of shape I’d gotten until, around last March or April, I found myself with only one pair of jeans that I could still barely squeeze into. The true nadir: The night Sarah and I went for dinner Calistoga and I couldn’t order dessert because (I shit you not) I was worried I wouldn’t be able to fit into that last surviving pair of pants the next day.

Something – not just the pants – had to give.

As regular readers will know, Sarah and I have spent the past few months killing ourselves at Orange Theory Fitness and Soul Cycle. The net result, apart from exhaustion and endorphins, is that I’m back to my ideal weight for the first time in three years. The downside: Before long I discovered all of my clothes were suddenly far, far too big.

As I stood at that sartorial crossroads – this would have been November or December of last year – I found myself thinking back to the clothes I used to wear in London. I turn 40 in 2019. Forty! Isn’t it ridiculous that I dressed more like a grownup when I was a drunk manchild than I do now as a 10-years sober author/founder who hopes to be a role model to two children?

I look back at photos of my dad around the same age and every one of them shows him dressed like an unequivocal grown up. Yes, he had to wear suits for work every day, but even on vacation, he always dressed like an adult (and indeed, still does.) One of my earliest memories involves me staring at my dad’s well-ordered tie collection and his rack of shiny dress shoes (not to mention his dress kilt, for formal highland occasions) and somehow understanding that these were the trappings of responsibility and maturity.

Every time I walk past Uber’s HQ and see the flow of identically schlubby proto-trillionaire sociopaths flooding onto Market Street, I’m reminded that grown men in startup t-shirts and baggy jeans is how San Francisco got into this fucking mess in the first place. And then I’m horrified at the idea that someone might see me in my H&M hoodie and think I’m one of those irresponsible, immature assholes.

Also, did I mention I TURN 40 THIS YEAR? Like the old woman who can finally wear purple and a red hat that doesn’t go, I literally can wear whatever I want. Sarah has written about this too: How once she became a mother and neared 40 she could finally channel her inner rodeo clown, with amazing cowboy boots and yoga pants paired with… wellI mean.

Perhaps that sense of liberation is what subconsciously pushed me through the doors of Tailors’ Keep – a made to measure/tailoring shop hidden in the shadow of the Transamerica building. Consciously, what drew me there was a Google search for somewhere that could re-hem an old pair of trousers and undertake a few other long-overdue repairs.  The Yelp reviews for Tailors Keep were tremendous – and from there I found this article about them in the Wall Street Journal, and this one in the Chronicle.

Still, I walked into the shop intending only to get those pants adjusted. Really I did. But then I was confronted with shelves piled high with fabric samples, and ridiculously patterned linings and buttons! So many buttons! I mean, it couldn’t hurt to look.

Six weeks after that first visit, I was the proud owner of a new, perfectly tailored suit, and two shirts made to my precise specifications.

Sarah’s reaction to just the suit was enough to dispel any possibility of spenders’ remorse. In fact, the per-garment price tag was less than I used to spend in my drinking days on clothes that didn’t fit anywhere near as well.

A few weeks after that I returned to collect four pairs of pants in a variety of tartans and stripes. Next: More shirts, and almost certainly some more jackets… the foundations of an entirely new grown-up wardrobe, in fact, tailored to exactly fit my new healthy self.

My god, where has tailoring been my whole life? Never mind the fit, or the quality, or the value for money…  who knew that there was a place in which you can sit in a big comfy chair and point at swatches of red tartan or purple stripes or Lichtensteinycartoon linings and a man with a tape-measure will transform them into an honest to god jacket?  

As Ryan – one of Tailors’ Keep’s founders – measured me for the suit, I realized another benefit of tailored /made-to-measure clothing: Accountability. My suit was due to be ready during the first week of January – which meant an entire Christmas clusterfeast lay between fitting and that first try-on. There was simply no way I could risk being unable to fit into my fancy new clothes because I couldn’t hold back from a second slice of pie.

(NB: I know I know: Food/fatshaming is bad. But what’s also bad is being a former alcoholic who, like a lot of recovering alcoholics, suffers constant sugar cravings. A second slice of pie often means a third, and fourth. You do you.)

None of which is to say that I recommend tailoring as a cure for addiction, or as a cure for much else except a surplus of closet space and a healthy bank account. But as a reward for ten years of sobriety, never mind all these months of gym-going, it’s hard to beat a pair of ridiculous green pants and a jacket with functioning sleeve buttons.

It’s also nice to know what it feels like a grown up, at last.