Style Inspiration Through the Decades

March 4th, 2011

“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

“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.

  • Grey “Prince of Wales” three piece flannel suit ·
  • Black bengal stripe shirt ·
  • Fur scarf Handmade ·
  • White linen pocket square ·
  • Burgundy ascot by Ralph Lauren Polo ·
  • Gold pocket watch Vintage from my late grandfather

1930’s – Manual Worker


“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.

  • Tweed Ivy cap by JCrew ·
  • Burgundy henley by Ralph Lauren Polo ·
  • Indigo denim jeans by JBrand ·
  • Brown leather braided braces Vintage ·
  • Brown leather boots by Red Wing

1940’s – Military Issued


“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.

  • Navy peacoat Vintage naval issue ·
  • Olive cargo pants from Army/Navy surplus store ·
  • Black leather alpine boots by Kenneth Cole ·
  • Navy cotton/ poly nautical stripe turtleneck by Caufield Prepatory

1950s – Grease-y Rebel


“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).

  • Black leather jacket by Ralph Lauren Purple Label ·
  • White cotton/linen t-shirt by Kenneth Cole ·
  • Indigo denim jeans by JBrand ·
  • Black leather wingtip boots by Paul Smith ·
  • Suede/leather driving gloves by Rag&Bone

1950’s Trad Prep


“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.


Pima Corduroy Trouser in Chestnut

White USA Oxford Shirt

  • Brown donegal tweed suit jacket ·
  • Striped Rugby Shirt by Michael Bastian ·
  • Navy polka dot bow tie by Polo Ralph Lauren ·
  • Burgundy penny loafers by Bass ·
  • Canvas & Leather briefcase by Filson
  • · White Oxford by Gap
  • · Brown corduroys by H&M

1960’s – The Rise of the Media Star


“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.


Donegal Tweed Suit in Monochrome

White Broadcloth Shirt

  • Navy flannel striped suiting tie ·
  • Black Seamless Lace-Up Shoes by Ferragamo Tramezza ·
  • Tie Clip by TheTieBar ·
  • Wool fedora by Rag&Bone ·
  • Pocket Square is a restaurant napkin
  • · Grey donegal suit
  • · White cotton dress shirt

1970s – Hippie/Free Spirit


“…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.


Blue USA Oxford Shirt

  • Navy Wool Cardigan by Polo Ralph Lauren ·
  • Slim washed denim jeans by Polo Ralph Lauren ·
  • White patterned tank top by PegLegNYC ·
  • White sneakers by Converse ·
  • Wooden shades by Shwood ·
  • Watch by Montblanc Timewalker Automatic ·
  • Bracelet from NYC street vendor
  • · Blue oxford cloth shirt by Thom Browne

1970s – Disco/Peacock


“…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.


Charcoal Essential Suit

  • Charcoal vest (part of suit) ·
  • Blue/Green Plaid Shirt ·
  • Navy Velvet Bow tie handmade by Carolina Montesino ·
  • Vintage Rainbow-Trimmed Doily as a Pocket Square ·
  • White denim jeans by Helmut Lang ·
  • Striped socks by Paul Smith ·
  • Brown leather wingtips by Gucci ·
  • Tortoise aviator shades by Persol ·
  • Brown alligator belt by Ralph Lauren Purple Label ·
  • Watch by Montblanc Timewalker Automatic
  • · Charcoal peak-lapel jacket (part of suit)

1980s – Power Business

Decades2 copy

“…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”.


Hairline Stripe Worsted Suit in Navy

White USA Oxford Shirt

1990s – Hip-Hop Movement


“…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.


White USA Oxford Shirt

  • Vintage varsity jacket ·
  • Jeans by APC ·
  • White air max sneakers by Nike ·
  • Watch by Montblanc Timewalker Automatic ·
  • Detroit Tigers Fitted Hat by New Era
  • · White oxford shirt by Band of Outsiders

2000s – Designer Minimalism


“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”.


Essential Worsted Suit in Navy

Textured White Broadcloth Shirt

  • Wool tie by Thom Browne ·
  • Silver sharktooth cufflinks by Jan Leslie ·
  • Sterling Silver tie bar by Tiffany & Co. ·
  • Brown leather wingtips by Gucci ·
  • Watch by Montblanc Timewalker Automatic
  • · Midnight navy suit
  • · White formal shirt

Thanks for reading.

Yours in style,

Dan Trepanier


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

Photography by Alex Crawford.