37 Indispensable Style Tips to Live by
It's my thirtysomethingth birthday. To celebrate, I've distilled a few (37) of the style lessons I've learned in my almost middle aged life.
I turn 37 (THIRTY SODDING SEVEN) on Tuesday. It’s an extraordinary shift in fortune which sees me become a year older than Princess Diana was when she died - an eventuality which seemed all but impossible back in 1997, when I was a mere sartorial tadpole in the style agnostic swaps of East Surrey.
To celebrate(/commiserate) the passing of the years of my life, I thought it would be useful and perhaps even fun (are you allowed to have fun past 35?) to pull together 37 key style lessons I’ve learned during my years on this weird, wild and wonderful planet.
1 | Buying expensive clothes won’t make you happier
It was recently brought to my attention that I have an acutely addictive personality. First I got stuck in with booze, then came substances. Eventually, booze and the other stuff had to go, running came next and most recently I’ve replaced it all with shopping.
Addiction, in layman’s terms, is the brain trying to source the dopamine that it’s lacking in any way that it can. The problem being that, no matter how many times you scratch the itch, a chronically dopamine-deprived brain is never going to be fully satisfied. It’s a point I’ve come to learn expensively in the last few months, spending a small fortune on beautiful clothes in the belief that they’d make me feel fulfilled. Spoiler alert: they didn’t.
So, instead of giving into the urge to shop I’ve instead started trying to reach out to friends with a phone call, spend time with my boyfriend, exercise or do things I love - like painting or playing the piano. It doesn’t mean I’ve stopped shopping completely, of course - I just bought a beautiful pair of Loewe loafers which I know I’ll treasure - but it definitely means that when I shop, I do so more mindfully. Investing only in things which I truly love (and which I’ll definitely wear a lot), and trying to buy said items solely with the money I make from selling my old stuff.
Shopping is great - clothes are wonderful - but they should only ever be seen as a glorious garnish to life, rather than a salve for its problems (because therein bankruptcy lies).
2 | There is power in owning a good watch
In my old life as style director of GQ and Esquire magazines I was lucky enough to be gifted a few beautiful watches. It wasn’t until I turned 32, however - when I signed my book deal and received the first instalment of my advance - that I actually bought a watch with my own, hard-earned cash.
I opted for a Rolex Oyster Perpetual 36mm in stainless steel and it instantly became the most beautiful thing I’d ever owned. It was expensive, yes - eye-wateringly so, at the time - but it was a true expression of my taste and it quickly became the only piece of jewellery I ever wore, the other watches in my collection quickly being relegated to the back of my safe.
I receive compliments on my watch all the time. It’s small on my wrist - so small, in fact, that at first I worried people might not even notice it. But the truth is that it’s a minuscule grenade of taste signification; one which applies the finishing aesthetic touch to all my outfits and adds a layer of elegance which simply couldn’t be achieved by the deployment of another, lesser accessory.
The lesson? Investing in a great watch is always a good idea. A Rolex, in particular - because so long as you take proper care of it and keep the box, you might just be able to sell it on for more than you bought it for.
3 | Nothing will make you look better than a regular haircut
It’s a long, hard-learned lesson that my hair always looks terrible if I leave it for any longer than six weeks between trims. In a matter of mere days I transform from well-coiffed urbanite to son-of-Catweasel.
As such, I try to get my haircut every month and a half, without fail. I’ve found a barber who I trust (here’s looking at you, Joe Mills of Woolf Kings X). He truly knows how to make my hair look its best, and for that I love him.
The six weekly cut is a ritual I follow with near religious fervour, knowing that even if my outfit’s a bit shit, my hair will look it’s best - and when it comes to good style, anyone who knows anything knows that’s half the battle.
4 | Moths will come
It’s a fact of life - like gravity or death - that clothes moths will find their way into your wardrobe at some point or other.
A few simple ways to hold off an infestation for as long as possible include hoovering your carpets daily, keeping the windows closed when you have the light on, and ensuring that any second hand clothes are properly cleaned before they enter your wardrobe. Oh, and invest in cedar hangers.
But the dusty winged suckers will find your cashmere eventually. My trick? Leave an expensive blanket in a prominent place and use it as a lure for moths, to try and tempt them away from the precious clothes in your wardrobe. I’m almost certain that it doesn’t work, but I find the fatalism of eventual moth dominion simply too depressing to acquiesce to without trying everything I possibly can, first.
5 | Thus, when buying vintage clothes, dry clean them first
It bears repeating that one of the best ways to avoid moths is to clean second hand clothes thoroughly before they enter your wardrobe. I’ve tried freezing my vintage finds, I’ve attempted to cook them (really), but the only thing which really works is a good dry clean. Expensive, yes, but less so than buying an entirely new wardrobe each and every spring.
6 | Conspicuous logos will always make you look insecure
Remember when logomania was a thing? If my Ryanair flight to Ibiza last week was anything to go by, it still very much is in some quarters.
Personally, a few remnants of the cursed period still exist in my wardrobe - a GG belt here, an LV monogrammed duffle there - but recently I’ve tried hard to purge every conspicuously logo-clad item I own (they sell pretty well on Vinted) because I’ve suddenly realised just how try-hard and insecure wearing them made me look.
If you really want people to know how expensive your clothes are, then you’re far better of relying on the fabric and cut to do the talking - both of which speak louder than you realise.
7 | Colour is yours as much as anyone else's
For years I entirely banned any colour - bar navy, grey, black or white - from appearing in my wardrobe under the misguided belief that I was not someone on whom reds, pinks, greens and yellows looked good.
How wrong I was! Sure, drenching oneself in a jarring block shade is always going to be challenging, but a well-positioned flash of scarlet (a tie perhaps), or a pop of pink (love a pink sock) can elevate a neutral outfit into something considered, playful and engaging.
8 | But learn which colour works best
Green is not my colour. It’s a lesson I’ve learned the hard way, investing in countless green shirts and sweaters over the years only to realise at the ripe old age of 37 that the shade has a tendency to bring out the yellow in my skin and ultimately make me look like a septuagenarian smoker with jaundice.
Pink, on the other hand, looks great on me - particularly if I team it with grey or midnight blue. Likewise Red, so long as I don’t let it dominate. Learn your colours and the whole, wide, wonderful world will become your chromatic oyster - because life’s too short to wear blue and blue alone.
9 | Always air your washing - even in winter
Nothing will ruin a good outfit more quickly than a cheesy olfactive spike of damp which denotes that your clothes a) haven’t been taken out of the washing machine quickly enough, and b) haven’t been aired properly as they dry.
Open a window, for pete’s sake. Even if it’s chilly. Your clothes - and the people around you - will thank you for it.
10 | Remember your waist
I’ve said it many times, but nothing - I repeat, nothing - is more important in the process of personal style discovery, than learning the soft power that comes with the accentuation of your waist.
Find one great belt in brown leather, another in black and put them to use with whatever outfit you’re wearing. It’ll tie everything together and draw the eye to the centre of your look, creating an air of considered cohesion and overriding any flaps of flyaway fabric.
11 | Cheap fabrics look cheap
Ok, cotton is cotton - and denim tends to be denim - but the truth is that high quality fabrics will make your body look better: they’ll hang better, stitch better, hold together better and reflect the light better than anything low quality or synthetic ever could.
If in doubt, therefore, avoid anything made from nylon, lycra, or any fabric fronted with the “poly” prefix, and instead aim for natural fibres which don’t cost less than you’d spend on lunch, because they’ll invariably look rubbish within a week.
12 | Failing it all, wear navy blue…
If you’re really struggling on the colour front, start with navy blue and work up from there. It’s a shade which flatters everyone (proper navy or midnight, not retina-searing royal blue masquerading as navy) and is a great backdrop for pops of colour.
A well-cut, single breasted navy blue suit will forever be the most adaptable garment in your wardrobe, so buy a few to be safe.
13 | …or brown
I discovered the beauty of brown late in my sartorial journey, but the truth is, it’s one of the most flattering and easy to wear colours on the chromatic scale. Soft, warm, it embraces its wearer in a slightly vintage-inspired hug.
Chocolate brown knitwear, in particular, is far too often overlooked in favour of washing out shades of grey and black (I struggle with black as, like green, it has a tendency to bring out my inner iron-deficient pensioner).
14 | Find a tailor and use him
Even if you buy bad clothes in cheap fabrics, a visit to a good tailor will make every single garment you serve him with look better than it would otherwise.
Find one you trust, stick with him or her, and don’t be afraid to furnish them with even the smallest of jobs - that extra half inch in the cuff will mark the difference between a good outfit and a great one.
15 | Never underestimate the soft power of a well-placed accessory
Coco Chanel famously decreed that every time one leaves the house, one should “look in the mirror and take one thing off.” This applies to accessories, certainly, but it doesn’t mean that you shouldn’t accessorise at all.
As per point 10, a great belt (I recently bought a skinny western one from Brunello Cucinelli which I’m absolutely obsessed with) or a neat little scarf will bring together an outfit and make it look like you care.
16 | Roll necks are actually quite difficult to pull off
I’ve tried for years to wear roll necks with suits - chunkier roll necks with jeans, too - but the truth is that unless you’ve thrown on an Aran clotted cream roll neck to see out on Icelandic winter, you always look a bit overcooked; like a man who wants to look stylish in an abstract sense, but also wants to hide.
I’ve come to the conclusion, therefore, that roll necks are to a wardrobe what concealer is to a make-up bag: useful for covering things up if you’re not feeling your best, but liable to look a bit smudgy and sad if not applied with care.
17 | I’ve said it once, I’ve said it thrice: Invest in a good steamer
Ironing is boring and labour intensive, a steamer works quickly and will make your clothes look one hundred times better than they would otherwise. Buy one. They’re cheap. You’ll never look back.
18 | A Uniqlo merino wool crew neck will be your forever best friend
I own a few Uniqlo merino wool crew neck jumpers in midnight blue and a few in black. Whenever I’m not sure what to wear, I throw one on under a jacket or blazer or and feel held together and smart.
They’re insulating in winter, breathable in summer, machine washable, affordable and they hold their colour. Nothing not to love (and arguably a lot less good than their pricier, luxury brand equivalents).
19 | Start using Retinol the moment you turn 30
I’ve been using a dab of The Ordinary’s Retinol 1 percent serum along with a smear or two of Aesop’s Perfect Moisturiser most nights since I’ve turned 30 and I’m sure it’s helped improve the quality of my skin.
My crow’s feet are less obvious and I don’t feel any compulsion to try botox, which I read as a good sign at the ripe old age of THIRTY SEVEN.
20 | Nothing makes you look better than sobriety
I stopped drinking at 34 and I’d be lying if I said that I didn’t stop, in part, because of vanity. Sure, my drinking had reached dangerous levels - I was doing it in secret and it was making me desperately unhappy - but I had also noticed that my face was puffy, my skin was red and my waistline was curvaceous, which was enough alone to make my capricious little brain want to stop.
Now, two and a half years in, I eat pretty much what I like (within reason), I exercise regularly, I fit into all my clothes, and I’m pretty sure I’ve never looked better. Sobriety is to thank. Sobriety is my twentieth style tip.
21 | But it is possible to be too thin
When I stopped drinking I also started running. I got very slim and although I looked great in clothes my skin became drawn and I looked a bit gaunt. Everyone benefits from a little of the under-skin scaffolding provided by facial fat as they get older - and nothing looks more stylish then a healthy, plump(ish) face.
22 | Learn to differentiate between great styling and good product
When I used to attend the menswear shows in Milan and Paris every season, my favourite was invariably that mounted by Prada. The main reason was that the brand’s clothes were worn in such interesting ways by the models - layered up and thrown over each other in ever more angular and unexpected ways.
It was a fascination which drove me to spend a lot of money in both Prada’s Via Monte Napoleone store. I remember one season - I think it was AW ‘19 - many of the models were held together with wraparound belts which were styled to look like corsets. Naturally, I went and bought one of the belts as soon as it was available.
Predictably, I’ve never worn it, because what I had been attracted to was less the belt, and more the aesthetic nouse of Olivia Rizzo - Prada’s long standing stylist. Turns out, the stupidly long belt itself was, on a muggle like me, nigh on unwearable. The lesson? Learn to differentiate good styling from good product and you’ll save yourself a whole load of money and wardrobe space.
23 | Hats are hard
Unless you’re bald, you’re engaging in a spot of early 20th century cosplay or you’re really cold or hot, hats are best avoided, as they nearly always look pastiche-y.
24 | Don’t scrimp on T-Shirts
I used to source my T-shirts from H&M until I started buying them from Sunspel and Studio Nicholson, and despite the considerable price hike, I’ve never looked back.
Not only do those from the latter brand keep their colour for at least 10 times as long as those from the former, but they feel wonderful against the skin no matter how many times you wash them.
Those from H&M, on the other hand? Let’s just call it the greaseproof paper effect.
25 | Don’t be afraid to go a size up
Sure, buying an XL might not do good things for your latent body dysmorphia, but the truth is that if your clothes are too tight, you won’t want to wear them (that is unless you’re Philip Green, who seems to relish dressing like an apple wrapped in cellophane).
Go a size up and enjoy the extra room. And then wear a belt! It’ll hold everything together without making you feel enclosed and claustrophobic.
26 | Never buy shoes which are too small
You won’t wear them. In fact, you’ll grow to hate them. Which is even worse, because then they take up space in your house which could otherwise be occupied by shoes which actually fit/you like.
27 | But If you do, remove the in-sole
Even if it’s glued in, whack it out and you’ll buy yourself an extra half size at least. Don’t be precious about keeping glued in-soles in, no one but you will ever see them and if it means you actually wear your too-small shoes then it’s worth the removal.
28 | Embrace the dad-ness of it all
The sooner you accept the fact that you’re eventually going to start dressing like your dad (in my case that means a penchant for boat shoes, roomy blazers, aviator shades and high-waisted jeans), the better. It’s inevitable, so why resist?
29 | Trust your instinct (if you like something, embrace it)
For ages I felt a bit embarrassed about the fact that I loved Giorgio Armani’s drapey tailoring. I resisted the fact that I had a thing for Tod’s suede Gomminos with little bow tied tongues - I fought against the fact that I adored Issey Miyake’s pensioner friendly pleats. It was a state of affairs which resulted in me wearing clothes which simply didn’t suit me (and, in turn, buying lots of logos).
Now, I’ve capitulated to the fact that I like the things I like for a reason and I should therefore listen to my instinct and continue wearing them because I LIKE THEM. And they BRING ME JOY.
30 | Ignore your trousers at your peril
British men have a terrible habit of ignoring their trousers, thinking of them as dual tube leg coverings which don’t need much care or attention - and giving in to dodgy skin-tight chinos from Uniqlo as an acceptable baseline instead.
The truth is that your trousers take up at least 60 percent of your outfit so they deserve as much attention as the rest of your garments (if not more so).
31 | Furry shoes are difficult to wear
I got into the habit of buying furry shoes for a while back in the 2010s because I thought they were fun, lux and showy in a kind of playful way. I bought a pair of shaggy calf hair desert boots from Prada (below), I bought a pair of pony skin loafers with neon pink soles from Marni and I bought some shearling lined loafer slippers from Gucci.
Apart from the latter pair, I’ve barely worn them because they make me look like Mr Tumnus. The lesson? Stick to leather unless you’ve got money to waste.
32 | Spray-on skinny only looks good on teenagers and/or models
The only people who look good wearing a skinny silhouette are Hedi Slimane, those under the age of 18, or heroin/Ozempic addicts. Avoid (even if the look does inevitably roll back into fashion).
33 | Socks over sockless
I love going sockless but the truth is that socks always look more elegant and grown up. That is unless you’re on holiday, the temperature is over 25ºC or you’re wearing sandals or mules.
A big, hammy ankle does not a good outfit make so if you do intend to go sockless, be sure to pick a wider trouser that makes your ankle look slimmer. Team with anything skinny and your leg will resemble a half-sheathed sausage.
34 | There’s a reason why shirts have been around for so long
Shirts are elegant, grown up and flattering. There is no reason why your wardrobe shouldn’t be populated with tonnes of them.
Just make sure your chosen shirt fits properly, that you buy something big enough to account for wash shrinkage and that the fabric is of a super high quality. That way you’ll wear it forever. Never underestimate the elevating power of a proper shirt.
35 | Freeze your knitwear
The only way to preserve the knitwear you love for as long as possible is to keep it in the freezer. Too much dry cleaning will damage the fabric, so pop your cashmere bests in air lock bags inside your ice box for ultimate elongation.
36 | Dressing like Princess Diana will always look stylish
Yes, I might despise the fact that I’m now older than she was when she died, but that doesn’t mean that I don’t appreciate how beautifully the People’s Princess once dressed.
A masterclass in perfectly-tailored blazers, high-waisted jeans, fun sweaters and Tees and easy wearing driving shoes, it was American Wasp meets British Sloane with a dose of Italian zhuzh mixed in for good measure.
If ever I’m unsure of what to wear in the morning I simply google “Princess Diana style” and copy her. And I shit you not, I am never not complimented for the resulting outfit. Never.
37 | Don’t buy clothes from Shein
It’s terrible for the environment, you’ll end up binning them because there’s no joy in wearing them, and you’ll treat them with considerably less care than you would something you’d saved up to buy.
Do the planet, your wardrobe, your skin and - ultimately - your wallet a favour, and buy quality clothes which you give a fig about instead.
If you’re enjoying The Closet - and/or you want to give me a nice birthday present - please consider upgrading to a paid subscription. It’s the cost of a coffee once a month and it will help me to continue producing this newsletter each and every week.
Hahaha the moths are a real worry I have sometimes, they even haunt me in dreams. I’ve tried the air clean cycle on my Samsung washer dyer machine on wool and now I feel a lot better. Can’t be completely sure it works, nor that it doesn’t. Makes me happy though. 🪰