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Sunday January 29th 2012



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A Century of Menswear – Decade Inspirations


“History is the best teacher” - ancient Latin proverb

It’s no secret that as we evolve, we continue to learn from our past successes and failures. The manner in which we present ourselves – including our personal appearance/image/style – is no different.

This is my dissertation – one (or two) look(s) inspired by each of the past nine decades in American history, along with corresponding style tips.

Please keep in mind that these are not costumes; the styling in these images is not meant to be 100% accurate for the decade. Rather, these are contemporary looks inspired by the said time period.

As always, all clothing featured in this article is from my personal wardrobe, and each look is one that I have worn at one occasion or another (or at least something very similar).

1920′s – Roaring & Fabulous

Grey “Prince of Wales” flannel jacket, double breasted peak-lapel vest, cargo pocket trouser, and black bengal stripe shirt all by Michael Andrews Bespoke (custom made, my own designs). Faux-fur scarf (folded in hand) and linen pocket square both handmade myself. Burgundy polka dot ascot by Polo Ralph Lauren. Vintage gold pocket watch (my late grandfathers). Wingtips by Scarpe di Bianco.

“The 1920s called for a fresh approach to dressing, which was epitomized by the new royal fashion Icon – the Prince of Wales, the future Edward VIII… Described as the best-dressed man in the world, the Prince was closely scrutinized whenever he went on tours, particularly in America, where every detail of his lavish outfit was reported on” (Blackman, 13).

Fashions of the “Roaring 1920s” were inspired primarily by royal figures. There was not much sense of “over dressing” or clothing that was “too” luxurious.

Take-away tip: Don’t be afraid to be the best dressed man in the room. You only live once – sometimes you deserve to feel a little lavish.

1930′s – Manual Worker

Tweed Ivy cap by JCrew. Henley by Polo Ralph Lauren (size M). Jeans by JBrand (Dylan, 34). Vintage leather braided braces. Boots by Red Wing.

“A collarless shirt, tough hobnail leather boots and a flat cap were the ‘uniform’ of the manual worker in 1930s Western society… [Since then] many items formerly associated only with workwear have entered the mainstream wardrobe, from construction worker’s boots to hardy textures such as corduroy. But one item of workwear in particular dominates clothing globally: denim jeans, which ironically now symbolize leisure rather than work” (Cally Blackman, 50-51).

Due to the stock market crash of 1929, and the ensuing “Great Depression”, civilian clothing was strickly rationed in the 1930s. Details such as trouser turn-ups (cuffs) and pocket flaps were banned, while designers were commissed to come up with utility clothing that adhered to such restrictions.

Take-Away Tip: A simple outfit with “harsh” fabrics such as raw denim, harris tweed, bridle leather and tough leather boots can be style-forward while remaining rugged and manly.

1940′s – Military Issued

Vintage navy peacoat (actual naval issue, size 38). Olive cargo pants from Army/Navy supply store (size S/M). Dark brown combat-inpsired boots by Kenneth Cole. Naval striped turtleneck by Caufield Prepatory (size 2).

“Many items of [military] uniform have travelled into the fashonale mainstream (in the late 1940s and early 1950s, much of it via the black market). Airforce bomber jackets, [camouflage pattern], Navy coats and heavy-knit sailor’s sweaters were taken up by youths who were lucky enough not to have had to wear them, some making them into symbols of resistance against conventional society along the way – and they remain fashion classics today” (Blackman, 50-51).

Take-Away Tip: Official military issued garments (think heavy wool pea coats, cotton gaberdine trench coats, leather bomber jackets, etc.) last the test of time – both because they are classic in style and very well-made. This vintage navy-issued peacoat, for example, weighs over 5 pounds and is virtually indestructible. This is the type of garments that I will wear for the rest of my life, and it will remain in good condition long after I will.

1950s – Grease-y Rebel

Leather jacket by Ralph Lauren Purple Label (size M). Cotton/Linen t-shirt by Kenneth Cole (size M). Jeans by JBrand (Dylan, size 34). Wingtip lace-up boots by Paul Smith. Suede/leather driving gloves by Rag&Bone (size S).

“The dress adopted by subcultures within the youth sector [defined by the new terms "adolescents" and "teenagers"] became a tool of defiance and political resistance, emerging as one the most significant influences on fashion in the second half of the twentieth century… The succession of subcultural groups such as the ‘Teddy boys’, ‘bikers’, ‘beatnicks’ and ‘hipsters’…identified themselves through a particular style of dress, representing a rejection of the older generation’s social and cultural norms” (Blackman, 144).

Take-Away Tip: You don’t have to “fit in” with what others are wearing, or what others think you should be wearing. There is nothing more bad-ass and rebellious than a fitted black leather jacket, white t-shirt and dark jeans – but that’s only because it was the original “f*ck the world” rebel outfit, because it went against the standard (see next image).

1950s – Trad/Ivy/Prep

Donegal tweed blazer (part of this 3-piece suit) by Michael Andrews Bespoke (custom made, my own design). Striped rugby shirt by Michael Bastian (size 50). White s/s oxford shirt by American Apparel (size S). Navy polka dot bowtie by Polo Ralph Lauren. Brown cords by H&M (size 33). Burgundy penny loafers by Bass. Briefcase by Filson.

“By their nature, subcultures [such as the ones discussed directly above] are minority groups: most teenagers were fairly conventional and subcultures such as the ‘beatnicks’ impacted very little, if at all, on the mass market and the clean-cut Ivy League college-boy look of sports jacket, Brooks Brothers shirt, chinos, penny loafers and short hair (not much different than the older generation’s style)” (Blackman, 144).

Take-Away Tip: Prep staples, although they will continually be “updated”, are easy to mix-and-match and will never go out style: tweed blazers, penny loafers, chinos, crewneck sweaters, oxford cloth button-down shirts, etc.

1960′s – The Rise of the Media Star

Grey donegal suit, white birdseye shirt and navy wool striped tie all by Michael Andrews Bespoke (custom made, my own designs). Black seamless lace-up shoes by Ferragamo Tramezza. 1″ tie bar by thetiebar.com. Pocket square is a cut restaurant napkin. Stingy-brim fedora by Rag&Bone.

“Film and fashion, like music and fashion, are intimately connected, never more so than in the decades after World War II. In our celebrity-driven culture, film stars act as conduits through which fashion can be disseminated” (Blackman, 216).

Stars like Cary Grant in Hitchcock’s North by Northweast (1959), Steve McQueen in The Thomas Crown Affair (1968) and Sean Connery as 007 in Goldfinger (1964) pioneered the iconic, monochromatic, slim notch-lapel grey suits, white shirts and skinny ties that dominated the mid 60s. Ironically, we have seen a modern resurgence of this look carried on by actor Jon Hamm as Don Draper in the popular 60s-based series MadMen.

Take-Away Tip: A no frills slim grey suit + white shirt + slim dark tie = elegant, classic, bad-ass.

1970s – Hippie/Free Spirit

Wool cardigan sweater (size M) and worn-in denim jeans (34×32) both by Polo Ralph Lauren. Blue oxford shirt by Thom Browne (size 2). Graphic print tank top by Pegleg NYC (size L). Sneakers by Converse. Wooden frame shades by Shwood. Watch and strap by Montblanc. Wooden, tiger’s eye and leather bracelets from NYC Street Vendor.

“…a new silhouette, as well as [the] increasing use of color and pattern [suggested] a fundamental shift in menswear that would explode into the so called ‘peacock revolution’… By the second half of the 1960s [and early 1970s] many were involved in the psychedelic counterculture that originated… Here, the hippies eschewed mainstream fashion for an eclectic mixture of ethnic jewelry, exotic, home-made and second-hand vintage clothing in their search for Utopia” (Blackman, 180).

Take-Away Tip: Flowy fabrics, bold colors and graphic patterns (best in small doses) make for an expressive, relaxed and approachable casual look.

1970s – Disco/Peacock

Peak-lapel jacket, waistcoat and plaid shirt all by Michael Andrews Bespoke (custom made, my own designs). Navy velvet bowtie handmade by Carolina Montesino. Vintage rainbow-trimmed “doiley” pocket square (my late grandmothers). White jeans by Helmut Lang (size 33). Brown/green striped socks by Paul Smith. Brown wingtips by Gucci. Tortoise aviator shades (in hand), alligator belt and silver engine-turned buckle all by Ralph Lauren Purple Label.  Watch by Montblanc.

“…it was a new generation of London-based  entrepreneurs that turned around the world of men’s fashion by addressing the demands of the young urban male consumer, who now wanted to dress differently from his father… Materials such as corduroy, satin and velvet were made into suits and hipster trousers in bold hues. Flowered shirts, colorful ties…tight jackets and wide lapels…appealed to both sexes” (Blackman, 180).

Take-Away Tip: Tailored garments can be fun and expressive too. A colorful plaid shirt, velvet bowtie and unexpected sock & pocket square are “dandy” elements that can help you stand out from the usual drably suited crowd.

1980s – Power Business

Double breasted navy pinstripe suit by Michael Andrews Bespoke (custom made, my own design). White club collar shirt by Polo Ralph Lauren (15.5 custom fit, tapered). Grey wool tie by Thom Browne. Gold collar pin by WANT. Gold tone watch by Nixon. Wingtips by Scarpe di Bianco.

“…the 1980s became a magnet for designers searching for inspiration. As a result, fashion, like musical genres, fragmented into a myriad of styles, each with its own dedicated band of followers” (Blackman, 242).

There were indeed a number of iconic styles that characterized the 1980s including “New Romantics”, “Goths”, “Punks” and (my favorite, and the most translatable to modern times) “Power Dressing” – Gordon Gekko style.

Take-Away Tip: Certain clothing displays power, authority, success, experience and strength in the business world. Double breasted suits, striped braces, contrast-collar shirts, gold accessories and strong pinstripes, for example, are very bossy and usually require “earning”.

1990s – Hip-Hop Movement

Vintage varsity jacket (size ?). White oxford shirt by Band of Outsiders (size 2). Jeans by APC (“new standard” size 32). Sneakers by Nike. Watch by Montblanc. Detroit Tigers fitted hat by New Era.

“…break dancers and rappers brought a new musical genre – hip hop – to the fore. They adopted sportswear: hoodies, designer tracksuits, baseball jackets, long shorts, t-shirts, baseball caps and lavish gold and diamond jewelry… Black style and music dominated our sartorial and musical culture” (Blackman, 242).

Take-Away Tip: White shirt (button-down or t) + dark jeans + white sneakers = “urban inspired” look that is casual, cool and swagger induced. This is a throwback for me personally, as it is reminiscent of my uniform all through middle and high school.

2000s – Designer Minimalism

Midnight navy suit (as featured a while back here) and white french cuff shirt both by Michael Andrews (custom made, my own designs). Wool tie by Thom Browne. Sharktooth hand-enameled cufflinks by Jan Leslie. 2″ silver tie bar by Tiffany & Co. Wingtips by Gucci. Watch by Montblanc.

“The suit survives, indeed thrives, in the hands of designers such as Raf Simons, Hedi Slimane, Jil Sander and Tom Ford. Skinny trousers, tightly cut jackets and narrow ties recall the slim, sharp bella figura silhouette of minmalism in the 1960s… The suit may well survive for another 350 years: it has never been surpassed as the all-purpose, universally accepted garment and essence of masculine style. Fashion is temporary but style, like the suit, is enduring” (Blackman, 286).

Take-Away Tip: Keep it simple, keep it slim. Take heed to the strong European influence in contemporary American menswear. More and more men are trading-in their oversized clothing and embracing a “slim fit”, a term that could be synonymous with “proper fit”.

Thanks, as always, for reading. The next “dissertation” will be less about the past of menswear, and more about it’s future ;)

Yours in style,


Bibliography: Blackman, Cally. “One Hundred Years of Menswear”. Laurence King Publishing, 2009

Photography: Alex Crawford.

Leave a Comment



  • Anonymous2 says:

    A slim profile is nice, to a point. But many of the outfits that guys wear these days look so ridiculously tight that it’s a wonder they’re even able to move around!

    It’s like they’re wearing leftover suits that they still have from 8th grade, and they resemble a marshmallow supported by two toothpicks.

  • Anonymous says:

    The outfit look great and cool.I really like it.

  • Military Camouflage Clothing says:

    Casual wear is my first choice.Some truly fantastic stuff here.I love it.your post is really very nice.thank you.

  • Mercedes says:

    Some truly fantastic stuff here! I’m digging pretty much everything but the 70s…did people really roll their trouser cuffs then? I feel like the flared pants of the 70s were the antithesis of these looks. The 6/1 double breasted is spot on!!! Totally cracked me up!

  • Anonymous says:

    I loved the inclusion of the fedora!

  • Anon says:

    You got a bit of a copycat on your hands :) guess your being admired


  • Wilhelm Meister says:

    good taste

  • Versus says:

    Well done! Impressive….although I would love to also see the inclusion of a 70s-style funky wide-label flared pants suit…like Teddy Pendergrass in his prime. Bit of Philly soul.

  • Brendan says:

    Amazing post. Trad/Ivy/Prep and Hip Hop Movement are my favorite looks but they all really do look great. That varsity jacket is perfect.

  • Anonymous says:

    SB i love this…probably one of my favorites.

  • fredrick says:

    I love it. puts a different spin on the blog.

  • Q says:

    Is that a 2.5″ or 3″ lapel on your Prince of Wales suit?

  • Matt says:

    great looks, will definitely be using some of these for inspiration. I like the theme posts and the effort you put into post quality. keep it up.

  • MS says:

    Dan, I’m curious how you reconcile certain eras of style— pre-WW2 and and the 90s, for example—where baggy clothes (including the Zoot suits of the 20s and 30s) were the fashion forward and then, ultimately, normative clothing choice. Where as I personally agree with you to some extent, your statement, “More and more men are trading-in their over-sized clothing and embracing a ‘slim fit’, a term that could be synonymous with ‘proper fit’,” seems erroneous to me in that you draw a value judgment on “slim” being “proper” when, in fact, baggy clothes were viewed culturally (and still are in some modern day cultures) as “proper”. I, for example, have one slightly baggy charcoal gray flannel suit—and while I appreciate a fine edged and impeccably tailored flannel—there’s something I find very comforting about this particular roomy flannel. It’s like a suit made out of pajama material or some such thing, a quiet, bizarre little rebellion of mine on a cold day, where I can be “formally” dressed and yet quite snuggly, if you will. I’m interested in your thoughts. Thanks.


    • SB says:

      Hey MS.

      By “proper” fit I simply meant seam lines hitting the body at their correct/intended places. Shoulder seams hitting at the correct shoulder point-to-point, waistband hugging the waist, outseams following the natural shape and curvature of the leg, etc.

      As far as your flannel “pajama suit”, I’m not sure I can get behind it. A tailored suit is almost always more flattering on the body – in my opinion of course.

      Thanks for reading.


  • DCRob says:

    The fact is I gave him praise for the other looks, however, Dan posts about being urban inspired and use to dress “hip-hop” prior to his transformation into this new modern man. In my opinion, he could have done a better job.

    I think he should have went with this look to be contemporary:

  • JK Ferguson says:

    What a great post. Fantastic ideas and outfits for the ages. Particularly enjoy the 1920′s manual worker and the 1950′s Trad/Ivy/Prep look. Never sure about that stingy-brim fedora. Something about it doesn’t look quite right to me.


  • Matthew Mejias says:

    Great job on this post… I think you did a fantastic job in encompassing the styles of the past, and making them appeal to the modern man. Keep the posts coming!! Thanks again…

  • CavalierandCotton says:

    whats going on Dan? Hope all is well! The blog looks great and this post is on point. Keep up the hard work. Check out my blog and let me know what you think. CavalierandCotton.blogspot.com

    Thanks man.

  • Anonymous says:

    Whats going on Dan? Hope all is well. the blog looks great and this post is on point!! keep up te work my friend. Check out my blog and let me know what you think. CavalierandCotton.blogspot.com Thanks man.

  • Christian says:

    interesting stuff


  • khordkutta says:

    “Please keep in mind that these are not costumes; the styling in these images is not meant to be 100% accurate for the decade. Rather, these are contemporary looks inspired by the said time period”


    Wow so quick to criticize.

  • FAIL says:

    The fits are not accurate for the time period. Tapered slacks in the 70′s? Come on man, it was polyester bell bottoms back then

  • Lavish-Livez.com says:

    The shoot seemed like it was fun!! Great outfits as always!

    I hope you and your readers stop by my fashion website!!


  • Jen_a_dandy says:

    I’m pretty sure he was just going for “inspired” looks, not “authentic recreations.” The look he is wearing he could wear (and does, I assume) today and still look stylish, but it has elements incorporating and reminiscent of the 90s hip hop era.

  • Sue/Mom says:

    This is awesome it is so well done….showcases what it important in fashion relating it to history, with a sense of humor and flair.

  • Anonymous says:

    Damn man, looks good, seems like it took a lot of effort to make this.

  • Toby says:

    I would be interested to know the source of the information that the US had clothing rationing in the 1930s. It certainly had war rationing of clothes in the 1940s, and not many people had money to buy new clothes in the 30s, but the latter (a product of austerity) isn’t technically rationing.

  • Jeff says:

    Nice work. I especially like the military style outfit with these Corcoran jump boots.


  • Mike says:

    The thing about you….effortless! Each look is so different, so indicative of the period, yet no caricature nor costume at all. Thank you for this forum for a guy who grew up in a place where guys didn’t care about such details. I hope I can reach your level of effortless-ness in my own personal style. Thanks for the help!

  • longgdivision says:

    @ DCRob

    “Please keep in mind that these are not costumes; the styling in these images is not meant to be 100% accurate for the decade. Rather, these are contemporary looks inspired by the said time period.”

  • Joey Dee says:

    I failed to mention above, that the 70s peacock look is so very english inspired and by far my favorite. I enjoy all the looks, but this one speaks volumes!

  • Joey Dee says:

    All these looks are great, the 20s, 30s, 50s, 60s, looks I especially enjoy. I believe that the eighties look would have been great with a dressed punk look, but other than that, there is always someting to take away from your posts. Keep posting, I will continue reading.

  • S. says:

    I love how you so easily pull of so many looks!

  • Anonymous says:

    This is the best post you’ve ever done, I must say, because it’s just so fun. Mind you, don’t stray from the advice, but I like the change of pace.

  • DCRob says:

    Also, the cardboard and boom box is early 80′s too. I think a 90′s grunge pic would have been better, IMO.

  • DCRob says:

    All the era’s on point minus the 90′s hip-hop. The jacket needs to be a satin Starter jacket (bulls, yankees, cowboys, or the U). The jeans are waayyyy too tight for that era, every pair was baggy. I do not know anyone that wore an oxford shirt either, needed to be a tee. Hat passes, but a snap-back hat was the true hip hop hat back in that era. You’re nike blazers are from the 80′s, you needed J’s or Air Force 1′s. And NO WATCH, beepers gave us our time back then. Not trying to be picky, that was the true style of that era. You have more of a 50′s school boy look…maybe it’s the jacket????

  • Travis says:

    Hey SB,

    I’ve been a follower since before you “blew up” and I have to say I think this is your best post to date.

    ~ Travis

  • Richard says:

    I’m intrigued by the quality of the execution of this. You amaze me, from your picture quality to your font choice. Great detailing.

    It’s funny to think like this but aren’t you born to be The Style Blogger?

  • MOZART5000 says:

    Epic inspiration.

  • Stephen says:

    Arguably your best work ever. Respect!

  • mjs says:

    Awesome post as always. Where in the city did you get the bracelets in the picture from the 70s? Been wanting some like that.

  • dsw says:

    How different everything looks when all clothes are perfectly fitted. Your blog is very good inspiration for me.

    Greetings from Poland

  • Robin says:

    Great work!!!

  • alec says:

    Awesome. Super cool post. I love this blog

    So many styles and my style is a combo of

    the 1950s and 2000s.

  • Mirko from Germany says:

    Why dont you start calling me Gordon?!

    Great Post!

  • Tom says:

    Very well done! Not sure if this is actually for school (or an exerpt from a project), but it is definitely a great outline for a school dissertation. Flawlessly executed.

  • Kin says:

    Amazing Dan.. Loving every bit of this post especially the rugged workers and prep/ivy look.. speechless

  • choosum says:

    there are a lot of blogs about style out there but you’re stuff is on another level

  • Rich says:

    Sweet post SB! Your prep looks like he’s about to get dunked on =)

  • CAS says:

    This just shows how versatile and deep your wardrobe really is. Also, I spy a leather braces trend emerging..

  • JMRouse says:

    Wow, you really outdid yourself this time Dan. This post is excellent and an inspiration.

  • Leonardo says:

    The best post i’ve ever seen here! Amazing!
    And congratulations for your work in blog, it’s simple and effective at same time.

  • jewvi11 says:

    nice work sb.

  • Barron says:

    Intense my man! Great work. Interested to see part two, your interpretation of the future of menswear.

  • Kofi says:

    Great Post you broke down all the various style from the different era’s in history, clever indeed I also have a blog that captures simplicity and elegance-we believe in originality. We range in style and showcase talented, creative individuals who strive and live to be original. http://www.simplebutelegant.blogspot.com

  • Sam Jacobs says:

    Very clever. Well done.

  • David says:

    Just wanted to let you know that I saw this post yesterday around midnight, and I see a ton of “test” posts on Google Reader.

  • Naldo says:

    Definitely a well detailed post. I am wondering where are the quotes from? All of them are spot on with the decades you represented

  • Michael says:


  • Anonymous says:

    WOW…….Theres no comment needed #enuffsaid

  • HN says:

    My favorite is the ‘grease-y rebel’. But they are all really well thought out and executed.

  • Erick says:


    haha that really was a great post and i loved how you hit every decade. i will definitely be referring to this post in the future.

  • cam says:

    i can definetly appreciate the research and writing that went into this. every look is really good except the the “hip-hop” look. i am a hip hop kid myself and from following your blog i know you are as well but that jacket and soft button-down looks more “Glee” than Jay-Z.

  • Wow! says: