If there is one thing you need to know about Award-winning fashion designer Michael Bastian, it’s that when it comes to American menswear and its various influences, he is a student of history. Growing up on the East Coast and attending Babson College in the 1980s, Bastian was surrounded by the influences that helped shape his appreciation for all-American Ivy League style.

We had a chance to sit down with Michael and discuss how what we know as the American men’s look was actually born out of the societal confluence of three historical trends. The result is a style of dress that was based on a completely new way of thinking about life, and it became a long-lasting trend combining classic elements of design and everyday optimism.

Michael points out that, as World War II wound down in the mid-1940s, young American soldiers began to flood back into the country at an unprecedented rate. Because of the newly created GI Bill, many found their way to college campuses across the country. These young men brought home with them a completely different perspective of fashion, borne of military necessity and focused on comfort.

Imbued with a more free-wheeling (for the time) sense of life, the daily wardrobe for these men was looser, tougher, more casual, and in many ways, more adaptable.

Comfortable khakis and cargo pants – literally everyday wear back on the battlefields of Europe and the Pacific – were paired with more traditional oxford cloth shirts and blazers. Rucksacks, once seen only in the field, appeared in classrooms hauling books instead of bullets. Sturdy field jackets, like the now-iconic M65, became standard wear.

Military gear has always had a place in the menswear space – it is after all the most masculine form of dress – but his was different. A fundamental change to the core elements of what American style is today is directly traceable to this post-war cultural shift.

Another growing influence at the time was sports. Collegiate athletics was fast becoming the new glue that bonded student to college and college to collegiate rivalries. Sportswear, inherently casual, began to work its way into everyday life, blending and melding with other active wear influences.

While today we may see polo shirts, sport coats, crewneck sweaters, and boat shoes as dressy casual office-wear, at the time adoption of these preppy staples into everyday use was a fashion and cultural sea-change.

The influence of sports and sportswear in American style continues to this day. And, with consumers continuing to blend dress and casual, formal and informal, the focus shows no sign of waning. Just look at Bastian’s namesake label and his work with GANT, now a byword for modern American prep fashion.

Lastly, there is what Michael calls the “Brooks Brothers” influence, which solidified these nascent fashion shifts into a new societal standard. A main stream, white-shoe influencer like Brooks adopting Harris Tweed odd jackets and Weejuns was the stamp of a new accepted menswear standard.

As the collegiate clothiers of the time, stores like Brooks Brothers, J.Press, Chip, and the Andover Shop where the foreword guard in this movement. They codified, as it were, these three disparate influences that reshaped what the world now accepts without question as the very definition of American Fashion.

Of course, American style is popular the world over. When we asked him what makes the American man’s look so classic and influential, whether in Japan or France, Michael had a simple answer. “Two things – an appreciation of a little of humor and personal style.”

Americans by nature are imperfect and we like it that way. Go to Italy, says Bastian, and you will see sartorial perfection. Indeed, the Italian man seeks perfection; his clothing fits just so, his hair is perfect, his shoes are shined. Imperfection is a sin.

In America, we celebrate the irony of imperfection and see it as an attribute of honesty and realness.

We also like to inject our style with some humor. We like frayed edges and scuff marks; we wear lobster print shorts and embroidered belts. We want things to show age and wear, and we value the personality earned by longevity (or just being manufactured to look that way).

With the influence of social media and blogs, the consumer now drives what’s cool and classic. We are a nation, a globe, of self-styled style auteurs with instant access to trends and brands, idea-shapers, and even designers like Michael Bastian himself.

No surprise then that our wardrobes’ naturally occurring scars of life have evolved into a style goal of perfect imperfection; a sort of meta sprezzatura. Think of it as the American contribution to global style dominance.

However, Bastian notes – and we wholeheartedly agree – that imperfection is not the same thing as shoddiness or being of poor quality. American style is essentially founded on the backbone of New England thriftiness; the idea that you pay good money for something of high quality and then wear it to death, patch it up and wear it some more.

Quality is paramount, and for those who truly appreciate it, there is no substitute. Don’t forget, all those great preppy classics were quite expensive back in the day. They were made well and meant to last. That’s why the style cognoscenti go gaga over vintage Shaggy Dog Sweaters, WWII-era chinos, and original Yale Co-Op GANT locker-loop oxfords.

The modern reflection of this value proposition is the current trend in “heritage brands.” Even brands that have no real history are seeking to sell their imagined roots and quality-driven aesthetic. And, while Michael feels that the heritage thing has hit a bit of an apogee and is starting to move on, true heritage brands – the ones that never placed trend ahead of commitment to making the best – will continue to benefit from the renewed awareness of value, quality, and craftsmanship.

Those same qualities are what led Michael Bastian to join forces with Frank Clegg Leatherworks in 2013 on a unique capsule collection, now in its second year. In addition to sharing an alma mater, Babson, Michael and Frank also share an obsession with quality and crating the finest products possible. The way that Michael fixates on what makes the best pair of khakis or the perfect button down oxford, Frank obsesses over leather.

“It’s a true family business, he and his two sons, and Frank is the best,” said Bastian. “Frank can’t sleep if he worried about how a piece of leather creased or bucked the wrong way. He is always thinking about leather.” Indeed, it’s a family fixation. Every bag, case, and accessory that comes out of their workshop is quite literally touched by a Clegg.

Incorporating an elegantly simple shield as the collaboration’s hallmark – a design element borrowed from a vintage U.S. Mail bag – the Michael Bastian x Frank Clegg capsule collection is a study in modern, masculine, classicism. These are bags to keep, and use, for life.

As we wrapped up, Michael told us a story that illustrated Frank’s absolute fixation on quality and perfection of his craft. Michael wanted to emboss his initials on a bag Frank was making for him. It’s not an unusual request, they blind emboss all the time. However, Michael wanted it done in gold. Frank said no.

The problem, he explained, was that most makers actually emboss using brass leaf, not gold leaf which is prohibitively expensive. Frank’s concern was that brass leaf might eventually tarnish or rub off. And to him that equals poor quality work, even though it’s unlikely anyone would ever notice and even if they did, would chalk it up to the patina of aging.

But Frank would know, and the idea of it would keep him up at night. Bastian went with blind embossing, as Frank suggested. Because, of course, exacting standards respects obsessive quality.