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Mr. David Shepard

This story originally appeared on the Gents Cafe Newsletter. You can subscribe here.


Meet Mr. David Shepard (@sidave) from Ann Arbor, Michigan, Global Applications manager for an advanced materials/chemical company.

David, how do you define your style?

More casual, but always trying to improve.

What does it mean for you to be a Modern Gentleman?

A modern gentleman can only be measured in my opinion by his interaction with others as there must be a reference or benchmark when determining whether a person is a gentleman. A gentleman is defined and measured by his interactions – verbal or physical – in the form of body language. The audience may be friends, family, colleagues, customers, or a fellow sitting at the bar next to you. I believe a modern gentleman is a person who can enter a room or new atmosphere and immediately participate in conversations regardless of the person or topic in which he is interacting with. Listening first and then providing input shifting the conversation to keep the others involved. The modern gentleman is much more than the superficial things such as clothes, jewelry, cars, etc. In my opinion, how a man builds and interacts with others during conversation is a true indication of a modern gentleman.

When it comes to style, where do you mostly get your inspiration from?

Instagram, not just doom scrolling through the “for you” page but inspiration from people I follow such as Noah Williams, Matt Hranek, Casper Lundmose, etc. and whose posts they re-share. The blogs that influence me are mainly Valet. and Huckberry Journal.

What’s your personal style signifier?

Driving loafers. Every day. My favorite brand as of recent has been To Boot New York. My only gripe with loafers would be their finite lifetime versus other types of shoes. I think this is a bitter-sweet relationship with the shoe, but the silver lining is the ability to constantly try new brands and styles. I’m pretty harsh on my shoes and the typical lifetime for a daily wearer would be 4~6 months.

What are your favorite wardrobe essentials?

A shawl cardigan, well-worn jeans, and a slim-fit cotton polo. My fiancé introduced me to shawl cardigans back in 2020 and I’ve been in a dire search trying to find one that has the fit, feel and pattern that fits “me” and as of now, it’s a Ralph Lauren. The jeans need to be slimmer at the ankle and I prefer them just a bit long so I can roll the cuffs when wearing loafers.

What are your main passions and how do you cultivate them?

Photography, cocktails, cooking, and watches. I’m always looking for inspiration to fulfill my passions for cocktails and cooking and this comes from visiting some amazing establishments in Detroit. The photography fits in perfectly as I’m always working to capture both the food and cocktails how I see them whether that’s at home, restaurant or bar. The last being watches and I’ve really enjoyed how watches ties into other hobbies such as whiskey, cars, cooking etc. My main inspiration for watches has been Hodinkee and the editors who write for them.

What does your ideal Sunday look like?

Waking up in the morning in my own bed with my fiancé, 75 pound Silver Labrador and our 6-month-old son Graham. The best Sundays start by scrolling TikTok with Graham while my fiancé gets ready for the day. Then taking Ellie for a walk and, on the return home, brewing an espresso. I’ve enjoyed having Graham press the buttons on our Saeco to brew the shot. I’ll enjoy my espresso sitting on the ottoman across from Graham in the lounge chair making faces and pinching his cheeks. The remainder of the day involves some form of exercising either on the stationary bike or a trip to the gym. The mid-afternoon most definitely involves a cocktail (Negroni or Old Fashioned) an episode of Mad Men (wherever I left off last… I’ve watched the series at least a dozen times and always catch something new), and lastly cooking a meal for the family.

Describe an interesting trip you have taken and tell us and what’s the next destination on your bucket list.

I was traveling all across the globe from 2013 through 2020 visiting customers to introduce or develop technology for emissions control applications as each country has its own regulations. I would often try to spend the weekend before or after customer visits to explore new cities. The most interesting trip was in February 2018, a weekend in Tokyo. I was just getting back into photography and my good friend stuffed an Olympus Stylus Epic Zoom loaded with a roll of film into my briefcase. I was staying the weekend at the Tokyo Hilton in Shinjuku. I had a few goals in mind which were eat local Japanese food, get a cocktail at Bar Benfiddich, and capture some photos worthwhile developing. All of which I was doing without speaking a word of Japanese and made an oath to myself I would call my Japanese colleague for any help in translation or support. The next destination on my bucket list would be Rome, Italy. I’ve visited Italy many times for work but I’ve only seen the inside of hotels, restaurants and airports. I have three simple goals: enjoy an espresso, a Negroni, and buy a pair of loafers.

Tell us what can never be missing in your liquor cabinet.

Bourbon, Carpano Antica Sweet Vermouth and a variety of bitters. The bourbon is important and Four Roses barrel-proof single barrels are my go-to. The high proof (typically >110) and age (typically >8 years) allow them to be enjoyed neat or in a cocktail. One of my goals is to further expand my knowledge regarding wine, and wine and food pairings. I’ve really enjoyed discovering red wines from different regions of France as historically I’ve leaned towards California red and red blends.


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