Self-Styled: What Changed in My Thirties

My first style post in ten years: new decade, new thoughts on living well.

My last post about personal style was a long time ago—a one-time attempt at this kind of writing (not fashion, not wellness, but something in the middle) when this site was new. I was in college at the time and noticed my style changing. College was the first time I had to be presentable in a way that mattered: I had to impress teachers, friends, and people who might someday offer me a job.

At university, I defined myself for the first time. Those high-stress years were so rich, so fun, and so meaningful; I would give anything to go back to those times. But they are gone—I’m thirty-two. I’m not sure my first style post aged well, but I did.

I am still not a big fashion guy, but I like how I look now more than ever before, and that feels good. Maybe that is the magic of the thirties. Liking myself feels like a magic trick I pulled off without being sure how I did it: I’m as surprised as everyone else that it worked.  

I still read (and love) several fashion magazines, but I stopped reading GQ years ago, after they let go of Glenn O’Brien, the original “Style Guy” columnist. More than an advice writer, O’Brien was a connoisseur of cool, a true man of letters who happened to tackle subjects of style and living in deft, deadpan prose. His resume was full of so many famous names and brands that it’s hard to say who he didn’t rub shoulders with. He hung out with Bowie, wrote for Interview under Warhol, and served as editor of Maxim and High Times; sometimes, Basquiat drew doodles in his apartment.

O’Brien wrote plays and books and hosted television shows. He partied hard in the 70s and 80s. He was part of a vanishing New York scene and wrote about it. His departure from GQ was bitter and made the magazine appear to be run sloppily, as it likely was—though, later, when O’Brien passed away in 2017, GQ's then-editor wrote a moving piece about him, as did every other menswear magazine that owed him an inspirational debt.

I read GQ primarily for O’Brien’s tips. In hindsight, I see my first style post here was a nod to him and those years in the closet when I read GQ as gay-adjacent media when anything more explicit was forbidden or inaccessible.

Thank you, Glenn. 

When living in the closet, style was dangerous. Lookign fashionable could betray you as a fag. Later, as proud fags know, style marked community and outness. Every crowd I tried to be part of, from art school kids to circuit gays, came with sartorial markers. Hipster wear gave way to harnesses and Nasty Pig jockstraps.

I don’t know how the chase ended, but it did at some point. I stopped trying on scenes through the clothing associated with them. I hit my late twenties, and somewhere in that hinge time, I figured out that the only person I have to be true to—the only one I need to impress—is me. That sounds hackneyed and saccharine, but it’s entirely true. It's the feeling of adulthood.

At dinner recently in Berlin, a friend teased me about my style. He was being playful, but it hurt a little bit. I thought my style had improved with age: now, style was just me, just my quirks. I saw him as very fashionable and still do, and although we did not wear the same clothes, I chalked that up to differences in style, not taste. But after his teasing, I wasn’t so sure he saw it that way.

Yeah, my Native-American style moccasins are ridiculous—and probably culturally inappropriate. Yes, my jewellery can tip into "white girl at Coachella" territory. I love feathers, fringe, and beat-up leather. Once, I showed up to a book reading event wearing my moccasins and a wool, ash-grey Stetson cowboy hat. My editor said, "Alex, you cannot play cowboys and Indians in the same look. Take one thing off." Lesson learned: Wear only one piece of cultural appropriation at a time.

Later, I talked to my friend about his words. He did not mean to hurt me and apologised. There was no need: feedback can sting, but it’s better to have people in your life whose tastes you trust. That’s my first style advice for your thirties: have friends whose tastes you respect. Their tastes don’t have to fully align with yours. That’s good. We style ourselves around the people we know, in conflict and communion with them; how we wear ourselves is as much a reflection of our friends as it is of us. My style evolved in Berlin, where the “desert shaman,” “Burning Man cowboy” look has weaker footing: this is the land of techno, not rock and roll or American folk. I can’t deny I’ve been influenced by the no-rules fashion of Berlin streetwear, by clubwear, and by the men around me I love.

I trust certain people (honestly, just two or three) to tell me when I’ve crossed the line from a “look” to a “getup.” However, the fact that my look can go too far—that I am playful enough with what I wear now to sometimes cross the line into “too much”—makes me happy. It means I have figured out something important: the things don’t matter. The stakes are low. Style is for play, for fun. The goal is to wear life like a loose-fitting garment. And: take one thing off (thank you, Coco Chanel).

When we are young, we care too much about what others think. Maybe we have to. In the young years, we try different scenes to see how they fit. But by the time your fourth decade of life comes around, you should know more about who you are and how you present yourself. You should have some idea of your career, your favourite and least favourite people, and the amount of money you can spend on this stuff.

One inspiration for this post was a recent article in Mr Porter, “How To Dress Well In Your Thirties.” It has good parts, like this bit, which rings true:

Entering your thirties often comes with a confidence and clarity of personal style where you’re no longer swayed by fleeting trends or conscious of what people might think and you start dressing for yourself. … “In my early twenties, I dabbled in styles and trends that were definitely not my style – which I knew at the time – but it’s easy to get swept up in the hype of products or brands,” Wightman says. “I have a much better grasp on what I like, what suits me and makes me feel my best.”

However, when you read a Mr Porter article, you must remember it's an advertisement, typically designed to make you purchase higher-priced items, such as suits, coats, dresses, and boots. It's not bad advice, just not for everyone. Working creatives dress differently than upwardly mobile yuppies in fintech—the class of people this article and others like it are aimed at. Since I don’t work in tech or finance, I will never again have to wear a collared button-down shirt, a wardrobe staple for most men, so I don’t own any. I hate them. As a creative, I’m allowed to live without them.

My advice now: Just have fewer clothes. I don't like owning a lot of things—in fact, I may be too eager to throw things away—so, for clothing, I cultivate a small collection of nice, well-made items. My home and wardrobe are not minimal to the point of being severe or monastic, but I try to keep everything intentional. My living space is impeccably neat, and this is reflected in how I keep my closet and, by extension, how I dress.

My wardrobe is mainly comprised of earth tones and neutrals, allowing me to pair any piece with any other, so that I can take the next shirt and the next pair of pants and put them together without worrying too much if they match. I like honey colours, ore colours: black, bronze, tan, brown (not mustard), and the like. My home reflects this, and so do my clothes.

Since it’s easy to make impulse buys from brands on Instagram, do this: make a list of brands that work for you. Once you find a good brand for trousers, stop looking for trousers. Divide this list into categories of types of clothing, since we tend not to like all products from the brands we buy from. I divide mine into the following categories: t-shirts, pants, jeans, casual jackets, dress clothes and suits, casual shoes, gym shoes, gym shorts, socks, underwear, and jewellery.

Under each category, I have three subsections: Buy, Try, and Never Again. "Buy" is for clothes I'll get again, tried-and-true things I know work. "Try" is for brands and clothes I've not tried, but might. "Never Again," of course, are brands I'll never buy from again, either because I regret those purchases or have simply outgrown their aesthetic. 

Some brands exist in multiple categories. For example, Y,IWO, a Brooklyn-based gym wear brand, makes great socks and gym shorts, but I'll never repurchase their t-shirts. Lonsdale, an English brand that specialises in boxing and MMA gear, also produces great underwear, and I'll never buy anything else from them.

I am 100% certain I will buy a leather jacket from Schott NYC one day—one of my most prized possessions is a vintage one, given to me by a friend—but I haven’t yet. (When I do, I will go to their beautiful flagship store in Greenwich Village and buy one there.) I have a soft spot for tattoo and rock and roll culture brands, like Straight to Hell, but these are now “Never Again”—they’re just not for me anymore. One day, I was shopping online and realised they’re for kids, and I’m not a kid anymore.

All the brands I list are in my price range. Few fast fashion retailers, such as Zara and H&M, are worth it, as I don’t think these clothes are worth even their low costs, nor are they environmentally friendly. But my list is not made of luxury brands: expensive clothes are still infrequent, special purchases for me.

I have some pricey things, but luxury does not compose the bulk of my closet. The money I could spend on more expensive clothes would be taken from travel funds, tattoo money, savings, and other things I value more than what I wear. If I had a style maxim, it’d be: “wear cheap clothes and expensive shoes”. That’s what I do.

The “Buy, Try, and Never Again” list keeps me shopping with intention. It shows me what I need and don’t: if there are “Buy” brands in each category, I’ve bought those clothes and, unless they get destroyed, I don’t need more. I feel I’m past the age of trying many new brands. I’m not sure how much longer this list will be helpful, since it doesn’t work for thrifting and recycled clothing, but it works for now.

Every six to twelve months, I discard what I no longer wear or donate it. Having less stuff keeps me happier and more organised, and makes me appreciate what I have. I don't buy "circuit clothes," "party clothes," or anything meant to be worn once.

Reuse clothes. I never buy gym shirts; instead, I take old T-shirts and turn them into "shredders" by cutting off the sleeves. I get summer shorts from old pants. New clothes are fun, but old ones have a lived-in charm that can't be bought.

I have areas where I splurge. I like good perfumes and good shoes. I love jewellery and keep mine organised in an antique jewellery box, a gift from a past lover who was a jewellery designer, and one of my great treasures. Jewellery lets me express myself, and jewellery best accents a muted wardrobe.

But how to define a personal style in the first place? I think it goes back to your friends. I am influenced by people I’ve crossed paths with, sometimes without their knowledge. (That ex-lover, the jewellery designer, put my self-image through the washer and I came out better, cleaner, improved, on the other side of him.) That said, a mood board helps. A digital mood board (some people use Pinterest for this) online or on your phone can help you stay inspired and maintain a clear style direction. If there are celebrities or film and TV characters whose looks you like, add them to it.

If you're nearing thirty, you've likely realised that skincare outweighs clothes. At night, I use retinol, and in the morning, I apply an astringent toner, followed by The Ordinary's Multi-Peptide + HA Serum, and then a moisturiser with SPF—every day.

The most significant changes in my self-care regimen since my last post have been showering less frequently, drinking more water, reducing my alcohol intake, practising daily meditation, and eliminating shampoo from my routine. After I stopped stripping my hair of its natural oils and styling it with heavy products, I discovered that it has a natural curl, especially when I let it grow out a little. Now, I just use a salt spray or a leave-in conditioner. When I was younger, I was told to use sunscreen more and not mess with my hair too much. I wish I had listened; my hair and skin are damaged, and I will be forever fighting that. If you haven’t started using sunscreen with at least 30 per cent SPF every day, start right now.

The trick to feeling good in my body now is to get enough sleep, stay active, and watch my sugar intake—all the things that kids don't worry about. The gym is necessary to keep my depression at bay; daily meditation keeps me anchored. My whole life is sobering, in every way; I have occasional, nice cocktails with friends. I don’t drink beer. Life feels clearer and cleaner—better—than in my twenties.  

I think it’s just about giving fewer fucks. Nearly every person older than me said how great it felt when they ran out of fucks to give, and boy, it does. More than ever, I appreciate my bookishness, my moodiness, and my sense of humour. I love the people I find interesting, the scenes I create, and how I decorate a room. 

All this is style. I’m not rich, but I’m more content with my money and my life than I was before. I have the privilege of being stylish and creative within a tight financial limit, and I appreciate the fact that most artists can say the same.

If you're hitting thirty soon, do not mourn your youth. Focus on what everyone is saying: your best years are ahead of you. Experiment. Play. To borrow a line from the aforementioned Mr Porter piece, now really is the time to tune into your frequency. You might like how the real you looks.

Love, Beastly