If you prefer to listen, the boys and I discuss this topic more “in depth” (if you can call it that) on the podcast proper. You can check it out below and skip to 28:16.

This is likely not a surprise to any of you, but I don’t really read menswear magazines, be it physically printed or through the interwebs. It goes without saying that most of such content is rather banal, being geared toward the basics (menwear advice hasn’t really changed in a hundred years) or being so focused on celebrities, trends, and the Zeitgiest that I feel old and isolated in how woefully unaware I am in what’s is shaping culture; I guess my TikTok algorithm is too honed into comparing different takes on the highnote in “Music of The Night” (Norm Lewis’s opt-up is my current obsession). 

Of course, like any good menwear boy worth his salt, I do own a handful of them: Japanese magazines released in the late 2010s (mainly 2nd, as it’s more sartorial than Clutch or Popeye), a few early WM Brown issues, a handful of gifted The Rake mags, and a beloved throng of 30s-60s Esquire that I’ve come across on my jaunts to various fleas. To be clear, my collection largely functions as an archive of inspo, a way to make my interest in menswear quite tangible. To be clear, I have actually read through a bit of it (the ones in English), where the best articles are the ones largely unrelated to men’s attire. I have yet to stay in a Rake-approved hotel or drive around Europe in a Fiat Panda like the Hranek family, but when I do, I know what to expect. 

That being said, I was “recently” reminded that I did have two particular Esquire magazines that were important to me. Not in terms of styling, I don’t think, but that they made such an impression on me and what menswear could be. And from what I remember, this was in the Before Times, as in the period not only before I started writing, but before I even started posting outfits, let alone wearing vintage tailoring. That was because these were Esquire’s Big Back Book, their biannual “style manual” full of style advice and recommendations, at least much more than their regular issues. My mom bought two of them for me when I was younger, likely in the hopes that I would improve my style beyond Hanes tees, plaid shorts, and flip flops– the attire of a grievously nerdy tween in the aughts. 

This was so long ago that I could only recall a few hazy memories. One issue contained a section on utilizing bold colors for Spring/Summer, mainly in the form of saturated jackets (I think there was a purple peak lapel number as well as a green blazer) and a gaggle of dusty chinos; this was inspired by my watchmaker friend Michael posting a fit with their parakeet green chorecoat with jeans and a tie. 

The other came to my mind a few years ago when I was writing my article on pocket squares. I shared a point on how the absence of a pocket square is an intentional move that I tend to leverage when my goal is dressing chic and intentionally reserved, serving to highlight the existing shirt/tie/jacket combo (which is usually minimal) instead of being a case study in maximalism and harmonic prowess. Even when composing it, I knew that my sentiment wasn’t an original thought because I had read it before in another Big Black Book. I remember seeing this sentiment shared alongside a dour model photographed in monochrome, not unlike the editorial work from Anglo-Italian.  

I initially wanted to source the mag for my own article, but I couldn’t find it or the issue that contained the peacocky colors that plagued my mind. Esquire’s archive isn’t publicly available, and I didn’t feel like subscribing or trying too hard to search. Fast forward to recent days, where I had some free time and decided to look again, ultimately coming across the vintage magazine subforum of The Fashion Spot…where a moderator by the username of “justaguy” had uploaded scans of each of the old editions of The Big Black Book. And thanks to them, I finally found those articles, which were contained in the Fall/Winter 2009 and Spring/Summer 2011 issues– two years that were indeed before I graduated high school…and before the firm start of my menswear journey. 

Nostalgia washed over me as I flipped through the virtual pages, skipping to find the article that contained that note on forgoing the Pocket Square. As I went through the mag, I noticed that a handful of the fashion contained within wasn’t too bad— and the copy wasn’t awful either. I decided to sit down and read it, internalizing the approach and attitude of the advice as well as the accompanying fits. What I found was something surprisingly endearing and ultimately quite different from most men’s fashion counsel I’ve seen today, be it from a publication or an influencer.

“Rule No. 1:  Be Quiet”.

It was just like I remembered: a fancy, italicized black font against a brick-red background. A commanding intro page that contrasted sharply with the monochrome photography that followed. At first glance, you would think it’s silly that Esquire used black-and-white photos in a piece on fashion advice, but it really was a smart and certainly effective move considering the subject matter. The whole piece was recommending you go understated in your sartorial attire; color was unnecessary in showcasing these styling cues.

Two of the recommendations immediately stood out to me as they were astonishingly quirky. One was about the barrel cuff and how its simplicity is a way to be “pragmatic”, helping a man avoid the “frippery” of cufflinks. In a similar vein was the aforementioned suggestion to eschew the pocket square– the move that has stuck with me for over a decade. The writer does mention that pocket squares are usually the move to make a wearer “a member of the make-an-effort club,” but this no longer has to be the case. “Reports of the death of the pocket square are greatly exaggerated, but its temporary absence suggests instead that you’re making an effort to keep things simple”. With the model styled in an austere outfit (a dark, solid suit and shirt with a Bengal stripe shirt), it’s hard not to agree with the writer’s suggestion. It looks pretty cool, effectively showing the dresser as unfussy. That’s when you notice that none of the other outfits featured in this section has a PS either. Looks like they put their money where their mouth is!

But as interesting as those two points were, the rest of Esquire’s advice in this section wasn’t exactly groundbreaking, at least to modern (and experienced) eyes. The writer goes on to recommend that the magazine’s readers wear a school tie (repps), try grey plaid suits, opt for white shirts, and wear a watch that is as straightforward as the advice and outfits contained therein. The only slightly quirky one was the recommendation of a madder tie (one of the first ties I thrifted was madder).  While these may work for beginners looking to shake things up, this counsel isn’t all that useful for an inherently classic dresser, as they may already do many of these moves and certainly own a white shirt and a non-nonsense watch.

It would be easy to call this banal and simply close the magazine, but the more I read and look at these images in this article, the more I actually started to like it…and understand just how different it is from most menswear content. And that’s a compliment.

The main difference comes right from the thesis of the article: “Be Quiet”. This isn’t simply a catalog of arbitrary trends or a list of specific product recommendations derived from trending pieces. No, this article is entirely about recommending a desired expression and providing moves one could take to achieve it. The copy is indeed flowery and can feel a bit much, but I still find it both direct and informational, as the writer blends guidance, history, and aesthetic evidence in each of the recommendations. 

In suggesting Madder, the writer speaks to its “dusky hue” and how its “matte effect” serves to calm patterns, “making for a tie that is both unmissable and restrained”. Likened to a black canvas, the white shirt is called to be paired with subtle ties and dark suits, again echoing the theme of being “loud” in your reserved demeanor.  This naturally leads to the plaid recommendation, which, when done in an understated way, can provide “dynamicism and youthful vigor”, especially when it’s matched with the other items in this article. The only time an actual brand is mentioned in the copy (and not the outfit breakdown) is in the endorsement of a “serious” coat, where their navy Chesterfield (for both the body and the velvet collar) is presented as more “killer” than a plain black one. I particularly enjoyed the reference to its history as a garment of mourning, as well as the cheeky line about how the shine of velvet “suggests something dangerous lurks beneath the sober surface”.

I’m sure that most of you will find the prose eye-rolling and idealistic, but I love it.  This might be due to my own insufferable mind, but I find the articles similar to music writing, specifically when it concerns evaluating orchestration, or the choice of what instrument plays what part, and how it affects the expression of the work.   The copy of this article is certainly more artful– or rather, the writer at least attempts to capture the art of dressing, highlighting how each component contributes to the attitude of an outfit, thanks to the garment’s construction (cloth, design) and inherent emotional attributes.  If anything, this approach gets at the joy of dressing!

The slight absurdity in using such language to describe clothes still feels like its still done in earnest, providing the prescription a bit of levity, even if it is potentially read as pretentious or pompous (which I think is entirely the point). This style of menswear writing is quite rare nowadays, outside social copy by The Anthology, what I remember from the now-private Adret, and, most distinctively, the articles of Die, Workwear.   Those examples, as well as this 2009 article in question, contrast strongly with menswear content today (both written and spoken via Reel/TikTok), which is either concerned with keeping up with trends or is simply geared to complete beginners (“what makes a suit jacket different than a sportcoat”).

Perhaps there’s something here about anti-intellectualism that leads modern publications to frame a suggestion of fisherman sandals by saying that they’re “originally beloved for being durable, quick-drying, and breathable [and] they’ve now undergone contemporary twists that add a sleek versatility to the look.” There’s no mention of what twists those are or how these pieces of footwear are sleek or versatile. Personally, I would have spoken about their elegant shape, the allure of their cheeky slits, and their old-world charm that brings about an ancient sense of ease. [Maybe it’s not that serious, but that’s what makes it fun!]

And even though this article is quite prescriptive (I personally read it as a suggestion, rather than an order), I noticed that the writer is still quite general in their counsel. I am referring to how the advice itself is not tied to a specific model or even brand, outside of the note to try a Chesterfield from Dunhill. Even though there is a breakdown of what the model is wearing (complete with prices), the author doesn’t list a particular Madder tie you must get, a fabric book for the right striped cloth, or a tailor to order a DB from. Advice without product recs is unheard of in menswear content, which is why I like it. Esquire puts the work effort back on the dresser, who now has to find their own way of approximating the recommended approach of “dressing quietly”. In that way, it can feel that the publication’s appeal comes from its taste by how it prescribes a vibe and attitude, rather than simply curating a shopping list of cool and trendy items.  As always, the best approach to getting dressed is by starting with a POV! 

The more I thought about the article, the more I realized that the whole thing reminded of Esquire’s father, Apparel Arts— in more ways than one. 

For those of you who don’t know, Apparel Arts was a trade publication meant to guide tailors and haberdashers in dressing their clients. As it was primarily concerned with styling, the magazine never named specific brands or products (though this was a time before design houses took hold of fashion). It also relied heavily on illustrations, though some photographs (even street style ones) did make it in. Overall, Apparel Arts was all about aesthetics and attitudes: a khaki suit (preferably gabardine) for a spring party, plaid tweeds when out shooting, and perhaps a poncho or espadrille for a beach vacation. It was all rather holistic, which is likely why the advice (and illustrations) still ring true today. The trade magazine gave way to Esquire in 1933, and both publications ran simultaneously until Apparel Arts was fully made to be more “civilian” facing, shuttering in 1958 with Gentleman’s Quarterly taking its place. 

To be fair, I haven’t looked at much AA after 1945 (when the post-war “Bold Look” replaced the trad/Anglo-ish pattern-mixing look the mag was known for), nor have I looked at Esquire issues before this one (I was a kid and my dad didn’t really read any Esquire or GQ). But if this Big Black Book is any indication, it seems that Esquire’s writers maintained a similar voice, at least through the aughts and early 2010s. But what’s even more interesting is that this throughline of taste and approach wasn’t just present in the copy, but in the styling itself.

I actually found the outfits in “Be Quiet” rather good…or at least surprisingly decent for the period of publication. Lapels are all moderate, trousers (and ties) aren’t too slim, and there aren’t any fat knots or extreme cutaway collars. And despite the article’s counsel of being restrained, the combinations themselves also feel delightfully interesting and quite trad. Plaid jackets are worn with a muted paisley and a solid grenadine, and there’s even a triple combo of a pinstripe suit, multi-stripe shirt, and dotted tie. Outside of the short coat and the cameo of a monkstrop, the outfits are all a bit “classic”, harkening back to the tasteful and exuberant looks from the bygone Golden Era Apparel Arts illustrations.  The vibe attitude even seems quite intentional, thanks to the use of thick-frame, retro-inspired glasses. All of it, combined with the monochrome photography and austere-yet-fun posting, ultimately exudes a chic, mid-60s vibe. 

It is crazy how classic and relevant these outfits (and advice) are. If you were to tell me that these shots were from The Armoury or Anglo-Italian, two brands known for classic and restrained styling (especially in terms of the latter), I’d have believed you! Hell, I’ve even worn similar looks myself, both in the past and today! 

Similar styling can be found in other facets of the two issues, though none of them are as striking as “Be Quiet”. Still, they serve to show just how surprisingly classic the menswear of this era used to be. 

In the 2009 issue, there is an article, entitled “Revisionists”, where design houses share their thoughts on the “modern” state of the suit, complete with some rather good outfits; a green tweed (paired wonderfully with purple) and a flannel jacket with hacking pockets (both in a 3-button) contribute more to the Anglo attitude, as well as showcases the various moods available to menswear-wearers. You can find striped shirts, classic-looking DBs (complete with wide-set buttons and styled with a block stripe tie), and a greatcoat shown as examples in the newspaper-esque “Information” sections. “Go Grey” and “Take Cover” are the other, suit-forward features but are quite milquetoast to the rest, with the only cool points taking the form of the suits combined with outerwear (all of which are cut a bit short), the use of a herringbone 3PC suit (complete with swelled edges and a lapeled waistcoat) and an unexpected fedora. 

The S/S 2011 issue is quite lopsided in how it handles classic styling with the bold statements of #menswear peacocking. That being said, I still find it fun and charming, in that it does remind me of some of the quirkier reccos found in Apparel Arts. Esquire endorses white suits, cream checked jackets, and white bucks (as wingtip oxfords, no less) in their essentials, something that seems more in line with, well, this damn blog than contemporary menswear media. An advertorial that name-drops Brunello Cucinelli) showcases Nantucket reds and brown suede chukkas. Unfortunately, the rest of the fits in that section (“Five Ways of the Summer Jacket”) leave a lot to be desired. There’s also an editorial on being inspired by maritime looks (“The Life Aquatic”), which maintains Esquire’s wry writing with some lightly cringe poses and outfits, all of which lean more Tumblr hipster than classic menswear (a start of the end, it seems). 

This focus on summer fun gives way to something a “better”: the aforementioned article on color, which, in a complete 180 from “Be Quiet” is full of saturated outfits and photographs. Each model wears something that is simultaneously preppy, Italian, and very early-2010s. The green blazer (in parakeet and moss) with jeans, as well as the glenplaid jacket worn with a magenta shirt, feels like something from early Sid Mashburn and Drake’s. [A few tweaks to the details/silhouette (go wider!), and it would be something I’d try my hand at; maybe someday, I’ll be able to return to bold colors.] The article does make good use of purples and whites, done up as DBs and chinos; even if they are giving Pitti Uomo, I’ll always have a soft spot for that look. Of course, some of the styling is a bit “bad”: there’s a shawl collar dinner jacket with a necktie, and pink pants, and there’s a deliciously hipster look of a linen scarf and distressed chinos worn under a Naples-yellow jacket.  Even if I wouldn’t wear the outfits verbatim, this article is still iconic to me, thanks to the clearly-fun styling, the writing style, and the intentionally irreverent poses. And like with “Be Quiet” and the section on forgoing the pocket square, I wonder if this 2011 shaped how I think and write about color.

What I didn’t expect (or rather, didn’t remember) was the editorial on wearing separates, entitled “The Anti-Suit”. This is where the issue lets the true Esquire Man shine forth, as the outfits are not only tailoring-first, but they all feature ties–- and a handful of striped shirts. One of them even does triple-pattern mixing! The slim effect #Menswear is certainly present (windowpane jackets, gingham shirts), but thankfully not its brashness. Everything is relatively reserved and tasteful, though again, not to the level of “Be Quiet” just a few years prior. Still, it goes to show that classic styles and Esquire Man-esque moves were still being implemented in the early aughts. It’s crazy to think about!

In closing, I want to iterate that I did not write all of this to say that “the aughts and 2010 had good menswear actually”, but rather as an exploration to see how much of it may have influenced my taste…and just how much menswear writing and styling have indeed changed in the past decade.  

Obviously, the approach in these two Esquire issues was never consistent, with both the “modern” and the classic being highlighted in the same issue. And for every artful and “non-specific” menswear prose, there are equally as many sale-focused, listicle-style pieces contained in both of these issues. The issues also contain a lot of basic advice regarding dress codes, the best travel bags to use, and what to say when you visit your tailor (for alterations and custom), though that makes sense considering how these are meant to be style bibles that Esquire releases twice a year. 

That being said, I still find these issues rather charming, and I don’t think that’s nostalgia goggles at play.  There is an endearing cheekiness present in these issues that I think modern magazines and greater menswear media tend to lack. The newspaper segments are a great example of that, like the grid of “important people” and how much to tip them. But as I said before, it’s really the way these articles talk about menswear, how they mix expressive analysis with earnest counsel– all with a soupcon of wit found in the Apparel Arts of old. Most of the counsel within these issues emanates from the expressiveness of menswear details and history, instead of its presence in the zeitgeist and algorithm. This approach is certainly a far cry from the content that glazes Jacob Elordi and JFK Jr., shares the shopping list to abet each season (and trend), or even the pessimistic, “gotcha”-style takes regarding Personal Style (how many times do I need say tha authenticity doesn’t mean original!), which ultimately leads people to look at the same sources of inspo and buy from the same, trendy places over and over again. Honestly, the key may just be that the Esquire of this period wasn’t social media-pilled.

It goes without saying that I have a bit of a soft spot for the styling, even if again, it’s not amazing and largely presents as “good” in comparison to what came later. Perhaps the reason why I am so steadfastly “trad” (in spades) today is that this was the menswear I saw and “grew up with” (to an extent, of course, as I soon fell into proper Apparel Arts and the Armoury/Drake’s soon after).  In fact, with all the focus on tailoring, these Esquire mags almost feel like they’re an inherently trad publication, instead of the general men’s fashion magazine they, and GQ, are today. 

If anything, it shows that this era was perhaps one of the last vestiges where suit-forward styling (done in a trad-ish way) was still en vogue in the menswear consciousness, or at least where publications are concerned. Of course, Esquire Man/Golden Era-adjacent styling was still found throughout the 80s and 90s in publications, brands (think Ralph Lauren and Paul Stuart), and on people in the street. My mutual Darren, a source of fantastic inspo, regularly posts a bit from his own archive of 80s/90s Esquire and GQ mags, proving that classic-ish style was still being written about, even if the looks are certainly reflective of their own times. Even though I prefer to share the root inspo from the 30s/40s, I do find myself saving some of those recently-vintage takes on Apparel Arts.  

I’d like to say this is proof that classic style will always ring on, but honestly, the real takeaway is that I really do just enjoy classic, sartorial-first outfits. I’ve planted my foot in a particular genre, likely as a way to step out of the social status (read: cool) driven approach to men’s fashion, and as a way to refine my own expression. After all, most of the inspo I save is “the same”, or rather, there is a clear throughline, no matter what decade it comes in. It’s just funny to see me find a bit of affinity for the 2010s, an era that we tend to turn a blind eye toward in the classic menswear world. I just wish that we took a similar approach to menswear writing today. It doesn’t even need to be focused on tailoring— I just want more artful, more expressive prose (or strive for it) when people talk about clothing.

Now, don’t expect me to make this into a series. I have no interest in reviewing more Esquire/GQ articles or even other menswear media from the aughts/2010s. But if I do come across more photos from that era that spark my interest (or find surprisingly delightful), I’ll be sure to share them. Of course, I’d really prefer just to keep posting my favorite Golden Era illustrations. 

– end of blog post – 

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Ethan 

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