An interview with Jack Simpson


September 6, 2018 by Ville Raivio

Age & Occupation

As most who find themselves in the creative field, I see age bias to be especially shortsighted.  Outside of my couture endeavors, I am a model, albeit one on a select basis. Age is an elusive factor, as an image of a senior man with a young woman is often of greater emotional interest than a similar photo with a woman of a certain age; the same is true for an older woman and a younger man. Giorgio Armani teaches us that age may even enhance one’s design vision, and, moreover, innate appeal. Mr. Armani and I have one thing in common: he started his business at the age of 40, as did I.


I had the good fortune to be awarded a Morehead Scholarship to the University of North Carolina, one given to those young people who show promise in both scholarship and leadership. However, I left after two years, perhaps naively so, for more creative stimulation.


Spouse & Children

My wife’s career has also been in the luxury apparel industry, and she is the only woman to have served as the North American agent for the revered cashmere brand Malo. One of my two sons managed a luxury menswear boutique at 25; the other is far too well-grounded to consider apparel as a career, even though we had a bespoke cashmere blazer made for him at four years of age. Both my wife and I shopped for the boys in Paris and Milan when they were very young. It now seems to me that it may have been somewhat frivolous, yet it surely instilled in them an appreciation for the value of refined self-expression.

The infamous cashmere jacket

Father & Siblings

One of my first memories of rejection related to the adult world was when my father, a long time clothing enthusiast, took me to the local menswear shop to be fitted for a sports jacket. The owner told us that I was too slight for any of their stock, a crushing moment then for me. I later worked, while in high school, for a similar independent specialty retailer of menswear, perhaps motivated by my earlier experiences; two of my three brothers did the same.

Jack Simpson MTO comes from the Martin Greenfield factory

Other Interests

My interests outside of clothing design are diverse.  Sport has long been a passion, and I served as both a head coach, as well as president, of youth football in the Connecticut town where we raised our sons. Both Formula 1 and IndyCar racing have long been of keen interest. I structured a deal for the company I headed at the time for an associate sponsorship of Paul Newman’s IndyCar team, and I often flew with him to races.  Paul became a client, and the suits we made for him carried his unique signature of classicism edged with irreverence. Each was made in a 4/1 DB with three open patch pockets…even his tuxedo. If one were to review my Instagram feed, you would find my principle subjects of interest to be period automobiles, the Golden Age of Hollywood, fashion illustration of the 1930s and 1940s, vintage furniture, and those gifted artists and painters whose voices reflected the intersection of color and movement.

First Inspiration

I read Ian Fleming’s James Bond novels in my early youth. The way he described the clothing and overall lifestyle moved me greatly, as later did the films. Sean Connery’s clothing in “Goldfinger”, especially the brown barleycorn tweed jacket, which was most memorable when he stood aside his silver Aston Martin in Switzerland, provided an invaluable lesson in masculine classicism and rakish male elegance. 

Gleaned Knowledge

My design aesthetic, both personally and professionally, has benefitted greatly from life experiences. I had the good fortune of being recruited by the noted designer Alexander Julian when his company was in its infancy. This gave me the opportunity to be involved in all aspects of the business from textile design to marketing. Alex, a five time Coty Award winner, taught me much. 

Design Influences

Elegance has long been a focus, and I have had the opportunity to create designs for a number of actors and statesmen who have been greatly admired for their sophistication and grace.  These relationships allowed me to study the presence, style, and personal presentation of each man.  Through my early attendance at the international trade fairs Ideabiella and Premiere Vision, I was exposed to equally elegant men in luxury menswear.  It is from these collective experiences that the lessons of taste and creativity remain at the forefront.

But I am also an avid reader, and the wisdom of a great many have influenced my design aesthetic. Among them are:

Oscar Wilde, “Consistency is the last refuge of the unimaginative”;

Lord Chesterfield, “Dress is a very foolish thing, and yet it is very foolish not to be well dressed”;

Charles Baudelaire, “Dandyism emerges in times of transition”;

Coco Chanel, “In order to be irreplaceable, one must always be different”;

Karl Lagerfeld, “Trendy is the last stage before tacky”;

Sir Francis Bacon, “Fashion is the only attempt to realize art in living forms and social intercourse”;

Diana Vreeland, “Style, all who have it have one thing…originality”;

David Bayles, “Craft is the visible edge of art”;

Frank Lloyd Wright, “Give me the luxuries of life, and I will willingly do without the necessities”; and

Harry Winston, “People will stare. Make it worth their while”.

House Style

We believe that style emanates from individual taste, and our house design centers on exacting architectural disciplines in model and pattern development, with the first objective to provide the client the opportunity of wearing a garment for upwards of 15 years. We also favor the idea of appropriate dress for every occasion. We encourage our clients to develop a balanced wardrobe; this includes elegant casual wear in addition to a tasteful, demonstrative professional wardrobe. Additionally, we believe that formal wear should be the most dramatic in the male wardrobe. Where anatomically appropriate, we think that these clothes should be steeped in an elan of natural glamour, with softly roped shoulders and superbly sculpted waistlines. Above all else, our design aesthetic subscribes to the twin tenets of classicism laced with wit, and of convention challenged by creativity.

Company Founding

When I founded the company in 1994, it was my belief that the world of designer menswear, which had been my professional focus for 13 years, and the world of custom tailoring would one day be merging. We were likely early in that reality, but it seems to me that this union is very much the case in the present day.

Couture v. Custom

The notion of couture was developed in Paris in the 1930s, with a one-on-one relationship between designer and client. In contrast, the modern day custom experience in America is rarely guided by the hand of an experienced designer. As such, our service is fundamentally different. Not only was my brand an exclusive at Neiman Marcus, I have also served as creative director and designer for Oxxford Clothes. This gave me the opportunity to work directly with textile designers in the finest mills in Europe to create proprietary fabrics, as well as to work with highly experienced pattern makers to create proprietary patterns. It is this body of knowledge that distinguishes our couture services.

Workshops and Quality

We have two levels of artisanal craftsmanship from our tailoring partners: bespoke and hand-finished, made-to-measure. When a man buys our suit, he is also buying our reputation, our tradition, our quality, our durability, and our value. The same is true for shirtings, for which we have both a made-to-measure factory and a full bespoke atelier, with whom we have worked with for 25 years. The Robb Report, in its 13th annual Best of the Best issue, named our made-to-measure suit among the world’s finest.

Brand Aesthetic

The most distinguishing feature of our service is the individual lifestyle approach to wardrobe development. Within our presentation, The Nine Categories of Dress for Accomplished Men, are over one hundred seasonal boards, each with a swatch presentation of complete ensembles. This allows me to study a man’s tastes and inclinations in order to nurture him through the wardrobe development process. Dress for men, be it for professional or personal use, has seldom been more confusing. Corporate America has shaken the very foundation of conventional business attire through the movement to casualization. Few men seem to understand the new rules; fewer still have the time to research the best options. I have spent my entire career in luxury apparel. Through interviewing my clients about their wardrobe needs, I have seen a pattern emerge. The lifestyle of the accomplished man demands that he have separate clothes for business, for high profile social occasions, and for formal events. Our goal is to design a modern wardrobe that fulfills all of a man’s lifestyle needs: designs developed exclusively for him in models created to flatter his physique.


I am informed by art and inspired by the elegance of the Golden Age of Hollywood. I am also challenged by the lifestyle needs of our clients.  After our inclusion in a feature on the world’s top custom brands in Departures magazine, the first five men to contact us offered the same personal insights: “I am in my late fifties and my wife is twenty years my junior. I want to change my look, but I do not want to look foolish.”


Style, to me, is the outward expression of one’s creative intellect. As my friend Bruce Boyer has written, “Real style is never right or wrong. It’s a matter of being yourself on purpose.”


The design process starts with color. In advance of each season, I develop concept boards with twenty key shades, as well as thirty additional colors to be used in complement. This palette is consistent throughout all categories and ensures continuity in overall presentation. If a man selects two ensembles, the shirts and ties will be interchangeable. 

The most expressive aspect of the men’s field is neckwear, and I turn to mill archives in England and Italy for pattern design inspiration, adjusting for scale and color pairings. That said, in menswear it is fabric that determines direction. I have long felt that the clothing must honor the cloth; this, without question, is the most pivotal aspect of design for the individual, as it instructs me on the nuances of cut, the elements of drape, and the line of shoulder for each of our clients.

1 comment »

  1. E.Hoskin says:

    Hi My name is
    E.Hoskin the owner of E&P Hoskin Custom Clothier i would like to know more about your company
    and like to no do you sale wholesale are your suits Ready To wear
    Or Made To measure.

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"If John Bull turns around to look at you, you are not well dressed; but either too stiff, too tight, or too fashionable".
~ Beau Brummell