How To Wear It: The Tudor Black Bay Fifty-Eight (2024)

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Welcome to "How To Wear It," where our Style Editor Malaika Crawford takes one beloved watch and shows you how to make it look its best – with styling tips and tricks, a delve into the current fashion discourse, some historical references, and a dash of British sarcasm thrown in for good measure.

I hereby present you with a watch that changed how I feel about all modern tool watches: The Tudor Black Bay Fifty-Eight (important side note – this photoshoot happened pre-BB54, which by the way, has me utterly spellbound).

This watch isn't exactly small, but for the sake of my argument, we're calling it "small/medium." At 39mm in diameter and 11.9mm thick, it's all in the profile; lean but supremely sporty, an overlap of descriptors that is surprisingly hard to find in the modern tool watch context.

Why does this watch stand out to me as a superior product? Listen, I came into this tool watch fellowship blind, with a mild yellow-gold superiority complex – a watch enthusiast who had never even considered the idea of wearing, let alone praising, anything modern made by Tudor (let this sentence confuse you or read between the lines here because 99% of watch brands suck at speaking to women). In fact if you had asked me what I thought of the brand before my much deeper foray into the watch world I probably would have scoffed, "Tudor, I don't think so, pass me the Rolex."

Rewind back to 2018, when this watch was released: The BB58 went against sizing expectations for dive watches of the period that tended to be bulky and large in case size. Here was a vintage-inspired watch that pulled on Tudor's historical ref. 7922 Submariner model but was executed in modern materials and came equipped with the in-house caliber MT 5402.

Shirt Lacoste; Earrings Stylist's Own

The BB58 lacks that top-heavy vibe that an overwhelming amount of sport watches seem to have (including the original 41mm Black Bay that preceded it). A clunky watch, no matter the diameter, is pretty much useless to me and my small wrists. The BB58 is not necessarily small, certainly not by vintage standards, but it's well balanced and svelte (ish).

I tend to veer towards modern when it comes to personal tool watch purchases – lest we forget that I am in my tool watch infancy, so who knows what will happen later down the line. I do like that the BB58 is versatile and durable. I do not have to be precious with it, in fact the less precious I am, the cooler it looks. Like a biker jacket or a pair of 501s, the point is to break it in and make it your own.

The price is another added bonus. Modern watches at this price point don't tend to fall under the watches-I-am-currently-lusting-after category. I'm not saying $3,950 is cheap – not by any means. I, however, lean towards yellow gold and jewelry-like design, so naturally that means the things I want aren't always within immediate reach. According to Google this makes me a sybarite. I think it just means I have great taste. Jury's still out.

Thankfully I am unbound by traditional watch-snobbery, so I can look at the BB58 through a slightly different lens. I absolutely love the idea of wearing a utilitarian watch for looks and not function. Even though the pink gold gilt is maybe a touch too much for my taste (enter the BB54, which is perfect – like I said more to come on this), I love the purity of this watch, the matte, date-free dial. Zero question, it's 100% better on a bracelet.

The very nearly perfectly executed vintage details make the BB58 design-y but still authentically sporty. It's full of tiny IYKYK details for all the vintage heads. Details (such as the red triangle at 12, the hash marks and thick bevels on the case) that render product less tech-y and more sophisticated. I have maybe rotated a total of four bezels in my lifetime, so I am truly paying attention to how this thing looks and not how to time a dive. Frankly, I'm not sure anybody buying this watch is timing a dive.

While 39mm is maybe a little above what I would go for on the diameter scale, I know it would suit plenty of women who enjoy a little more heft and wrist presence.

This is for my women who like a happy medium. A happy small/medium.

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I have this deep fascination with women who wear techwear outside of the gym. I see them parading the streets of uptown Manhattan – Nike Dri-FIT tops, Alo yoga leggings and Hoka sneakers. It's a uniform.

I, personally, hate wearing athleisure. Actually, I truly detest it. Unless you are mixing a pair of Nike Gyakusou track pants with a Celine by Hedi Slimane tweed jacket, please, keep it away from me. Martine Rose x Nike is about as far as I will personally go before I feel like I've lost the plot.

As per usual I am full of contradictions because I live for a sporty watch. The BB58 is sporty but it's sporty and elegant all at once. Like country club sporty, or croquet on the lawn sporty, NOT triathlon sporty.

Preppy sportswear is a whole category unto itself. The polo shirt is the universally acknowledged preppy emblem. Should you happen to have been a child of the millennium, the nostalgia factor sparked by a Lacoste polo is undoubtedly immense.

This, however, isn't the Lacoste polo as worn by Marissa Cooper in The OC. No, this couldn't be further from the layered Y2K pastel and popped collar polo shirts of 2004. Those were tight and clingy and for teenagers. This is the Miu Miu FW22-inspired version of preppy. Wear it like you would wear the BB58: a little loose, a little baggy, a little nonchalantly.

Shirt Lacoste; Pants Hermès; Shoes Gucci; Earrings Stylist's Own.

Every woman in my age bracket and beyond will relate to the eternal basic t-shirt / button down / collared shirt / polo shirt conundrum. How tight? How long? Crew neck or scoop neck? Rolled sleeves or loose sleeves? White or off-white? It's hard out here for a style-conscious consumer.

A year or so ago I had a very sudden adult sartorial epiphany – I'll call it Malaika vs the "Baby T." For those of you who aren't familiar, the Baby T is the young woman's t-shirt du jour. Often very cropped, and always very tight. These t-shirts are an emotional trigger for most women above the age of 22.

And so, my inner monologue (laced with a healthy amount of trauma from my mother's unabashed critique of my appearance) decided to confront my t-shirt fetish: "You are not 16 years old, you must transcend the Brandy Melville paradigm." I moved myself along to Petit Bateau (very chic and very French). Time for a grown-up t-shirt: well-cut, with sleeves that hit midway down my upper arm, and a hem that falls below my hips, a little clingy, but not too much, tight in the right places. I own about 10 of these tshirts and two of these classic Lacoste polos. They are on constant rotation. Trust me, these pristine white shirts will change your life.

The real win is that owning these shirts gives you permission to be a little lazy, you just throw the shirt on with whatever else you feel like wearing on your bottom half: a pair of blue jeans, a black a-line skirt, a tailored pant; your options are endless. The key to success is all in the mixing and matching. The polo is sporty, so wear it with perfectly-cut leather trousers and heels, not leggings and sneakers. It's all about the contrast (see sweatsuit with Cartier Tank Cintrée) and how a basic piece interacts with the other more interesting pieces in your wardrobe. The white shirt struggle is always worth it in the end; a crisp white t-shirt or polo will make you look clean and put together, no matter how messy your apartment or your brain is that day.

While I love to think about some of my favorite fictional characters playing tennis – Charlotte McDougall at Bunny McDougall's country estate in SATC or Brigitte Bardot in Belle Du Jour – this polo shirt isn't about tennis, It's about looking effortless, like you've tried, but not too much. Because all we can hope for is to look like the woman who opened her wardrobe, grabbed the first three items in front of her and somehow managed to emerge looking perfect – aka Kate Moss circa 2007.

Same goes for the watch. Throw her on like you just don't care. This whole outfit would change if you were to wear it with a Cartier Tank. A pique polo and a tank is chic but very lady and very considered.

And while leggings outside of the gym give me the ick, praise be for Claire McCardell, the most influential women's "sportswear" designer of the 20th century. She pioneered casualwear for women with her pragmatic approach to garments; forfeiting waist or dart lines in favor of roomy and flattering cuts. And while McCardell may not have envisioned her liberal approach culminating in the women on the Upper East Side and beyond running around in techwear, I'm pretty sure that with foresight, McCardle would have encouraged us to wear something like a BB58.

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Jacket Cherry Vintage; Pants Khaite; Bag Louis Vuitton.

Recently while reading Rachel Tshajian's newsletter Opulent tips, I was reminded of style icon and Yves Saint Laurent's muse Tina Chow. Bonne-Vivante and 1980s disco queen, Chow was the kind of woman who made very fashion forward clothes look easy, sexy, and cool.

She was, as Tshajian so accurately described, a "great collector of clothing – of Balenciaga, of Alaia, of Chanel." This speaks to my obsession with owning clothing like you would own objects. Owning them and loving them and curating them – like a watch collection!

This Rive Gauche Saint Laurent jacket is very Tina Chow. This is not an easy jacket. Wear with caution! For those of us brave enough, wear it with very skinny pants, lean back and imagine you are Diane Keaton in her black and chrome, Wassily chair laden apartment in Baby Boom (before the baby) or Brooke Shields being photographed by Patrick Demarchelier in the late 80's.

This outfit also screams Bonfire of the Vanities – read the book as a social critique of New York City in the 1980s or watch Brian De Palma's very bad movie rendition for very good wardrobe direction. Just make sure you dilute Melanie Griffith's outfits a little because we are not trying to parody – we are drawing on silhouettes for inspiration.

There's a fine line between looking like you are wearing vintage YSL and looking like you are wearing a heavily discounted '80's suede jacket from Etsy or your local thrift store. Trust me, I know from experience. You might be able to find a one-off gem, but chances are you'll end up wearing some hideously executed, overly shoulder-padded, patchwork, gold zig-zag-stitched jacket of horrors.

Jacket Cherry Vintage; Pants Khaite; Shoes The Row.

Yves Saint Laurent, the master of a perfect silhouette, had the enormous foresight to take items traditionally made for men and re-create them for women (watch brands take note!). Le Smoking, which came out in 1966 – a tuxedo with smoking jacket made for women – was a complete culture shock for the time. Tuxedos were worn by men, who after dinner would retire to the smoking room to smoke cigars and talk politics and economics. Creating a tuxedo for women was not only about taking the visual codes of a masculine silhouette and reconstructing them for a woman's body, but it was also about the implied idea of women now being able to smoke, wear pants, and talk business.

I think there is something supremely powerful about intentionally designing a watch for a woman. Can we please pay attention to what women actually want? You can sell me a watch designed for men at a smaller diameter, like this BB58 and I will gladly partake. But let's learn from monsieur Saint Laurent, who clearly had the foresight to understand that it wasn't about gender prescription but about crossover and intentional play on the design binary. And then in a perfect world, to then eventually dismantle the binary altogether.

The objects and clothing Saint Laurent created led to very strong images captured by the likes of Helmut Newton and Guy Bourdin, images that we still reference today. And these pictures of the classic Saint Laurent woman undoubtedly contributed to the visual discourse of second-wave feminism. Which goes to show how fashion imagery can have a massive impact on the construction of feminine identity (again, watch brands, take note!).

Yves Saint Laurent shaped the way most women dress today, the longevity of his designs stemming from the fact that his work was all about the purest of lines and simple silhouettes that were perfectly embellished. And I think this goes for all types of design. Get the foundation right and embellish as you see fit. Case in point – the Black Bay heritage line.

After a long afternoon staring longingly at countless images of Chow wearing Yves Saint Laurent, I felt like I was suffering from Stendhal syndrome. That kind of high octane glamor just does not exist in the same way anymore. Plus, Chow was ahead of her time; she was minimalistic in a decade of opulence. The 1980s version of 2010s Charlotte Gainsbourg wearing Nicolas Ghesquière era Balenciaga smoking a cigarette.

Replace your large and gaudy earrings (which are by the way my favorite type of earring but too predictable here), with a perfectly sized dive watch. Sometimes all you need is one very good accessory, and then sometimes you need a yellow Louis Vuitton handbag too.

I love the BB58 as a point of contrast to a very glamorous look. Like wearing sneakers with a suit or a t-shirt with a sequin skirt. And before you call me out for harping on about not wearing tool watches with a suit or tux, that rule does not apply here. Wearing a tool watch with a chic outfit is a power move.

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Shirt Comme Des Garçons; Skirt Louis Vuitton; Shoes Cherry Vintage; Socks Stylist's Own; Tie Hermès.

I'm not going to challenge the fact that wearing a tie as a woman is one of those very tricky styling decisions that can either turn out very right or end up looking very wrong. Blindingly perfect examples include Diane Keaton in Annie Hall, Julia Roberts at the Golden Globes in 1990 and Willa Bennett (EIC of HighSnobiety, whose uniform includes a perpetual silk tie rotation). But mis-step this one and you will end up less Louis Vuitton Fall Winter 22 looks 1 through 3 and more local politician does business casual, or worse yet – Blake Lively on her pantsuit infested press tour for A Simple Favor.

Spiritually I long to subscribe to the suit-and-tie combo a la Marlene Dietrich, but I am not that woman. If I was, I would wear a tie exactly as pictured below. I do not see watches and ties as some sort of sartorially banded brethren. Watches are far easier to master than ties. Ties feel like a corporate symbol of conformity, which makes me shudder in a way that watches do not. And the last thing I find sexy is conforming to a male trope. BUT, if you are that woman who can do the tie thing, and turn a trope on its head, I celebrate you. That is no easy feat.

Watch aside, this look is a play on proportion and gender. The white Comme Des Garçons shirt is a little commercial nod to the genius of Rei Kawakubo – the grande dame of deconstruction. Kawakubo, known for her experimental cuts and proportions, forces the CDG wearer to rethink notions of beauty, notions of the body, to rethink what fashion is and what wearability even means.

Here we have a simple white button-up shirt with balloon sleeves, a watered-down version of the CDG spirit that contests the rigid conceptions of masculinity and femininity (often conflating the two). Kawakubo's more avant-garde runway pieces refrain from shaping the female body, rendering the shape androgynous.

While this particular shirt isn't necessarily a political statement, the soft sleeves are a contrast to what is usually a very constricting piece of clothing. Severe and straight from the front, balloon-shaped and playful from the side, and tucked into a denim pencil skirt with red platform shoes. This is basically young Jodie Foster 2.0.

The watch looks very much at home here. It's less about making a statement and more about being the daily beater that goes with your Comme Des Garçons or your vintage Saint Laurent. This is not about wearing a "man's" timepiece, or boardroom cosplay, it's about wearing what makes you feel good. A robust sports watch can be versatile on a woman. Nothing wrong with wearing it like it's an accessory (because it is), as opposed to wearing it not like a token of your manhood.

I'm not sure Tudor's decision to shrink their dive watches has anything to do with widening their gender appeal as a brand. I think it's far more likely that this is about appealing to a wider pool of both vintage and modern enthusiasts. So even if this watch was a happy accident for women watch wearers, I will take it. Better to claim something and make it your own then let the marketing lords decide what you should and shouldn't wear.

Back to my eternal internal dichotomous monologue about fashion and watches. The key sentiment to take away here is that we should be dressing for pleasure. Why should wearing a watch be so serious? And why should every single expression of your personal identity be so considered? Have you ever considered the idea that wearing things can just happen on a whim or that a fondness for a particular product can simply be innate?

What I do appreciate about watch collecting is its inherent difference from fashion as a culture of non-stop novelty. I respect the idea of buying things you will keep for years and years. So if you are in this for the long-haul, then consider the BB58 as a daily beater, as a part-time sidekick or as the watch that you sometimes break out when you wanna feel a little more heft on your wrist. It's whatever you want it to be.

Shirt Comme Des Garçons; Skirt Louis Vuitton; Tie Hermès.

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