Conversations with men of style
SEAN O’PRY
Award-winning Model and the Face of Our Reserve Collection
What does it take to become the best at something?
Perseverance, laser focus, determination and an undying belief in yourself.
What advice would you give to your 18-year-old self?
Say, “Yes,” more.
What makes something a classic?
The ability to be worn in multiple settings and combinations.
Why is quality more important than quantity when curating your wardrobe?
You want to be able to pull styles back out 10 years later and find new purpose and combinations for your pieces.
What comes to mind when you hear something's handcrafted in America?
Top materials, quality design and that it’s built to last.
What makes something qualify as luxury to you?
Something that, once worn, gives you more confidence.
Mason Wingtip in Walnut
Maxwell Derby in Chili
Murray Brogue Captoe in Walnut
Maddox Boot in Coffee
Andrew Weitz
Entrepreneur, Editor and Style Consultant
“My personal style mantra is - Style. Confidence. Success. You are your own visual business card. Wear your look with confidence and don’t be scared.“
How do you define "luxury" and how has this word evolved culturally?
Luxury refers to a state or condition of great comfort, elegance and high quality. The concept of luxury has evolved from being focused solely on material possessions to covering a wider range of experiences, services and values. In today’s world, it now reflects changing societal attitudes toward sustainability, ethics and exclusivity, while still encompassing the comfort and elegance that defined it in the past.
What comes to mind when you hear something is handcrafted in America?
I think of quality and attention to detail. Handcrafted products often imply a higher level of craftsmanship and personal touch since they involve skilled artisans investing time and expertise into creating each item. That can lead to a higher level of quality, durability and uniqueness compared to mass-produced goods. The notion of “handcrafted in America” also emphasizes a sense of pride and tradition. I always gear towards anything handcrafted.
How do you define a classic?
To me, a classic is defined as something that stands the test of time, possesses enduring quality and is recognized as a significant contribution within its field. It represents a timeless and enduring aspect of culture and continues to be valued and appreciated by generations beyond its creation. In fashion, a classic style is one that remains in vogue no matter the passing trends. For example, the Chelsea boot will never go out of style. Aspects of it may change but, the boot itself is a classic. That’s why I believe so many of Allen Edmonds shoes are considered classic styles.
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Salomon DuBois
Model, Chef and International Tastemaker
“I believe that true style is an extension of personality, a reflection of confidence and comfort. My approach to fashion is to seamlessly blend classic elements with contemporary flair, creating a look that is both timeless and on-trend.”
Salomon DuBois
Model, Chef and International Tastemaker
Describe your personal style mantra and your go-to, signature styling tip.
My personal style mantra revolves around the idea of effortless sophistication. I believe that true style is an extension of personality, a reflection of confidence and comfort. My approach to fashion is to seamlessly blend classic elements with contemporary flair, creating a look that is both timeless and on-trend.
When it comes to my signature styling tip, I swear by the power of accessorizing. A well-chosen accessory has the ability to elevate any outfit. It could be a statement watch, a carefully curated collection of rings or the perfect pair of sunglasses. Accessories not only add personality to an ensemble but also provide an opportunity to experiment and express your unique style.
How do you define a classic?
A classic in the broadest sense is something that has enduring value, timeless appeal and a lasting relevance that rises above the trends of a particular era. It is a standard of excellence, widely recognized for its quality, design or significance and often serves as a reference point for others in its category.
What is your go-to shoe style?
My go-to shoe style is one that seamlessly balances comfort and style while adding a touch of versatility to my overall look. A pair of boots always finds their way into my wardrobe for several reasons: blending timeless elegance, versatility and comfort, they become the ideal companions for my dynamic and diverse lifestyle.
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Josh Peskowitz
Editor, Creative Director, Designer and All-around Menswear Expert
“My personal mantra is ‘Does this make me laugh? Or at least smile?’ I try to wear things that make me happy, and that are made by people I either know personally or by reputation. My signature styling tip is that it doesn’t matter how many patterns or textures you’re wearing if the colors are complimentary.”
Tell us about your life's work and the inspiration behind your personal legacy.
My life’s work has really centered around trying to give people (and men specifically) the perspective, and to a certain extent the permission, to express themselves through their clothing. What one wears says a lot about them, and the choices one makes when it comes to fashion have huge socio economic, environments and human rights implications. With all that gravity, it’s always struck me as odd that people want to say fashion is frivolous. It should be fun and make you happy but needs to be considered carefully. I’ve also always tried to champion lasting style, quality, and craftsmanship. It’s part of the reason I’ve always admired Allen Edmonds.
Define "luxury:" how has this word evolved culturally?
I think people have lost the distinction between what is luxurious and what is expensive. For me, luxury generally means that something is made the old way. It used to be the only way, but now it’s the hard way. The way that many pairs of hands need to touch (or just one pair, many times) and that gives a product a sense of being cared about. Taking the time to make something that lasts is a luxury.
What comes to mind when you hear something is handcrafted in America? Why is this meaningful?
I feel pride and a sense of loss. So much of the manufacturing base in this country is gone, and in many meaningful ways that has made us culturally poorer. Quality and pride of craft are embedded in the American consciousness but have become vanishing thin on the ground here. That’s why I am always happy to see and support brands that still make it happen here.
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Nick Wooster
Editor, Creative Director, Designer and All-around Menswear Expert
“ Buy the best you can afford. It really is the most thoughtful way to consume and to build a killer wardrobe.”
Tell us about your life's work and how you got to be where you are today in the industry.
I’ve worked in and around fashion since 1976, when I was a junior in high school. I never understood what it meant to work in fashion. Only that I loved clothes, and I was interested in the clothing business. The only job that I understood innately was being a buyer and that’s how I started my journey and career in New York during the 1980s.
Where do you draw your style inspiration?
I draw my style inspiration from everywhere. I’m never not looking. I look at everything. Horrible, sublime, mediocre, everything can be a source of inspiration.
Do you have a style mantra that you try to live by?
Probably the best piece of sartorial advice anyone ever gave me is: Buy the best you can afford. It really is the most thoughtful way to consume and to build a killer wardrobe. I don’t know that I have a signature styling tip, but one thing that most people don’t want to hear is: If you have a choice between something classic and something a bit trendier, buy the classic.
How do you define luxury and how has the idea of luxury evolved over time?
I think luxury has always been synonymous with something rare or difficult to have. It’s not meant for everyone. Today, people equate luxury with logos. This is the opposite of luxury. I also believe taste is a missing component along with knowledge. These are ideas that the great merchants of my early years understood and imparted to their customers and employees.
What comes to mind when you hear something is handcrafted in America? Why is that meaningful?
It’s meaningful because it’s so rare. Sadly, so much institutional knowledge has been lost, but it’s so wonderful when you find craftspeople that can still make beautiful things in the United States. It’s something to be treasured and nurtured.
How do you define a classic?
A classic is something timeless. If it was great 50 years ago, it will be great 50 years from now. Goodyear-welted shoes, brogues, derbies and Chelsea boots are examples of classics. So is a navy three-button blazer and a grey flannel suit.
What is your go-to shoe style?
Brogues, derbies and Chelsea boots in equal measure. They’re great with edgy, contemporary pieces and they always look polished and put-together. I’m wearing exactly the same shoes I’ve worn since high school.
Why are legacy and authenticity important?
Because they stand the test of time. There’s nothing worse than a new, cheap blue oxford cloth shirt. And there’s nothing better than an authentic old one.
What wardrobe pieces are always worth the investment?
Coats, jackets, shoes and watches. Everything else is negotiable.
