A stylish conversation with Stefan Dobrescu — Style Consultant and Founder of "The Gentlemen's Order"

Dear readers, with the arrival of a new season, it’s the perfect time to refresh your wardrobe with some key pre-Fall or Fall pieces. For many, the thought of reorganizing the closet can be daunting, which is why seeking advice from a stylist can be invaluable. A stylist who truly understands your personal taste and has a sharp eye for what works, while keeping stepping in tune with today’s menswear trends, can make all the difference. Mr. Stefan Dobrescu, a style consultant based in Romania, is deeply passionate about classic menswear. He is also the founder of the style platform and YouTube channel "Gentlemen's Order", where he shares his expertise with those intrigued by timeless men’s style and the art of dressing well in the modern era. Beyond his consulting work, Stefan partnered with an Italian shoemaker to create a limited-edition collection of wholecut Oxford shoes, a testament to his dedication to quality craftsmanship and classic style. In today’s conversation, Stefan shares insights about his work, his passion for classic menswear, and offers styling tips for the upcoming Fall season. Without further ado, let’s dive in!

My Modern Darcy: Hi Stefan, it’s great to have you here. As starter, what is it about classic menswear that fascinates you? Was this something that interest you from your childhood?

Stefan Dobrescu: Hello My Modern Darcy, thank you for having me. The way I see it, back when classic menswear was in its prime, so let’s say the 1920’s to the 1950’s, society valued beauty - you could see it in art, in music and definitely in men’s style.

Gentlemen used to dress in a way that presented them in the best light possible, not only by accentuating certain physical qualities, such as broadening their shoulders with padding or increasing their perceived height through vertical stripes, but also by always striving to look presentable and professional. Nowadays, trendy styles are all about who is more comfortable or even vulgar and that is why I will always prefer classic menswear.

For me, this interest started quite young. At the age of 13, I wanted to look more mature and masculine than my jeans-and-hoodie self, and I found inspiration in classic films like Goldfinger. “If those men could wear suits every day and look so confident and in charge, why can’t I?”

MMD: Could you tell us about your path to becoming a style consultant? What inspired you to pursue this career?

SD: It is my opinion about men today who often struggle to find positive role models. You have one side shouting about “toxic masculinity” and the other equating masculinity to violence and bravado, but very few mainstream voices guiding men to be both intellectual, refined and empathic, as well as confident and tough: a true gentleman. That’s why I set out to help young men discover the “Cary Grant” within themselves - someone who embodies elegance, intellect, and strength in balance.

I began posting videos on Instagram in April 2023, and a few months later, I expanded to YouTube, where I could share more in-depth advice. At first, I tried to answer as many comments and messages as possible to support individuals directly, but over time, I realized that offering style consultations would allow me to put my knowledge to better use and create real, lasting change in people’s lives.

MMD: What does a typical day look like for you as a style consultant? How do you usually work with your clients? And what do you find most rewarding about this work?

SD: By day, I work as a software developer in banking, and by night I dedicate myself fully to menswear — reading, creating content for YouTube and Instagram, and working with a select number of clients. My goal is to steadily expand my client base as demand grows, but right now my schedule can’t allow it.

When I begin with a new client, the first step is always understanding his goals and lifestyle. Does he want to project more professionalism and trustworthiness, or boost his confidence in social settings? From there, we define a style direction that suits him personally — for one man it might mean sharp tailoring, while for another it could be a more relaxed, preppy-inspired look. Together, we refine his wardrobe, keeping only what serves him and adding timeless pieces that will last for years. Finally, I show him how to combine the items and create outfits that showcase his personality.

What I find most rewarding is seeing how style impacts lives beyond clothing. When a client tells me his confidence has grown, or that he even found the courage to walk up to the girl he likes and ask her out because of the way his clothes make him feel, those moments remind me why I do this.

MMD: In today’s casual dress culture, why does classic menswear continue to hold value? What makes its presence significant in our time now?

SD: Classic menswear is based on timeless principles of proportion, balance, and harmony. It considers attributes like complexion, hair color, height, and build, and applies rules that bring out the best in the wearer. For example, a striped suit might elongate the figure of a short gentleman, and a contrasting outfit will better match a contrasting complexion. Classic menswear, therefore, is scientifically proven to bring out the best in the wearer, and that’s why it is also known as the “eternal fashion”, it focuses on you, not on the trends.

MMD: Your YouTube channel "Gentlemen's Order" offers insightful tips on dressing well. How do you define a well-dressed man, and why do you think this matters today?

SD: First and foremost, a well-dressed man is one who dresses with intention; he knows that his clothes tell a story and he chooses to convey one every time he walks out of the house. In doing so, he makes an effort to present his best self to the world, and in our hyper-casual culture, even something as simple as chinos and a crisp white shirt can make him stand out. The way you dress reflects the level of respect you have for yourself, and if you don’t respect yourself, how should others? This of course, does not mean that you have to wear a suit every day, just to know when it’s time to outgrow the graphic tee and sneakers.

MMD: What are some challenges you’ve faced in both your consulting work and running your styling channel? And how have you overcome them?

SD: In any endeavor, you will encounter criticism - some of it will be constructive, while the rest will simply be the result of damaged people trying to lift themselves up by bringing others down. One of my biggest challenges so far was learning how to respond to hate and realizing that you can’t help everyone, because if someone does not want to change, you cannot convince them otherwise. What I’ve learned from this is to focus my time and energy on those who are actually motivated to make a change in their lives.

MMD: As we slowly enter the Fall season, could you share your style insights? What are the key pieces to invest in, and what color palettes and silhouettes do you recommend?

SD: No matter the season, I’m always a fan of earth tones, and they’re especially striking during the fall. That’s why I recommend muted shades of green, beige and brown. There are a few key pieces that I consider essential for the fall season: an olive waxed jacket for casual outings or any activities in nature, a long khaki trench coat for rainy days, a brown herringbone tweed sport coat for business casual occasions, high-waisted flannel trousers perhaps in grey or even (a bit more daring) cream, and a pair of Goodyear-welted Chelsea boots to tie everything together. These items are not only timeless, but also practical. Oh! And also, a bunch of sweaters - one can never have enough of those.

MMD: You collaborated with an Italian shoemaker to create a limited-edition shoe collection. How did this partnership come about, and how does it reflect your work and personal style?

SD: The collaboration came about when Andrea, who is a very talented Italian shoemaker, reached out to me by email. I was immediately excited by the idea of a collaboration and very happy to share his work with my audience. I always advise people to invest in quality, and Andrea’s shoes are exactly that: they’re handmade in Italy and feature premium quality leather.

MMD: From your perspective, what defines a well-made pair of shoes? What details will you look into?

SD: Interestingly, a well-made pair of shoes has many of the same attributes as a well-made suit. First is the material, which in this case is the quality of the leather. Next is construction; for durability and longevity, I recommend shoes that are either Blake-stitched or Goodyear-welted. Design is equally important, so I suggest timeless styles such as cap-toe Oxfords, double monks, or penny loafers. Last but not least, we have the fit. Does it really matter that your shoes were made by Church’s or Crockett and Jones if they are uncomfortable and you will never wear them?

MMD: Let’s discuss your personal style, how would you describe it? What is your go-to or favorite outfit? Are there any style icons that inspired your choices?

SD: I have never actually considered a “go-to” outfit, but now that I think about it there is one that stands out: During warm summer days, I like wearing this lovely three piece off-white linen suit, paired with a pin-collar shirt by Edward Sexton, an ivory linen tie, and a white Panama hat. I also enjoy wearing double-breasted blazers, which I believe to be one of the most underrated garments in menswear. Overall, my style is a blend of vintage inspiration and Ralph Lauren aesthetics, but I naturally also draw inspiration from classic icons such as Cary Grant, Humphrey Bogart, Sean Connery, and Roger Moore, as well as from certain movies and Pinterest.

MMD: When choosing clothing, what criteria do you consider? How do you balance creating impeccable outfits while staying true to your personal taste?

SD: I mostly focus on classic wardrobe essentials. Sure, sometimes I deviate from this, but there’s little sense in buying a pink cardigan that I’ll wear once or twice if I don’t yet own a cricket sweater, which is a true staple. I also like to focus on quality and I have been distancing myself more and more from both synthetic fabrics, as well as fashion forward brands that try to do everything without doing anything particularly well. In time, I have also created a list of personal favorite brands that I like to frequently revisit, though I am always happy to discover new ones.

MMD: If you had to pick three items in your wardrobe you couldn’t live without, what would they be and why?

SD: That’s a tough one. First, I would have to say my made-to-measure navy double breasted blazer - simply one of the most underrated garments in menswear. It’s incredibly versatile and can be dressed both up and down. Second, my mid-grey chalk-stripe double-breasted suit - every man should own at least one suit and this one is my current favorite (though that might be recency bias). And finally, my 1994 Omega De Ville. Beyond its timeless design, it carries sentimental value, and I think every man should have a watch that not only completes his outfit but also signals that he means business.

MMD: What does the word “style” mean to you? What key elements do you believe that can make someone sophisticated and stylish?

SD: In the immortal words of Yves Saint Laurent, “Fashion fades, but style is eternal”. For me, style is about presenting yourself with intention and maturity, in a way that feels timeless. If an outfit would have looked good 50 years ago and will still look good 50 years from now, that’s the essence of true style.

MMD: Beyond being well-dressed and well-groomed, what qualities do you think a modern gentleman should possess?

SD: There are many qualities that define a modern gentleman. He should be well-read and well-traveled, intelligent yet modest, ambitious yet disciplined, and charismatic while remaining composed. But above all, I believe a gentleman must have a kind soul — showing compassion, loyalty, sincerity, and a genuine concern for others. In a society that thrives on gossip and envy, the greatest mark of a gentleman is his ability to hold on to his humanity.

MMD: Finally, if someone asked you how to become a great style consultant, what is your advice?

SD: A great leader, in any field, always leads by example. I wouldn’t be where I am today if I hadn’t kept an open mind and stayed willing to learn. Over the past decade, I have improved my style by 1% every day, by reading books, analyzing different outfits, as well as trying different things to see what works and what doesn’t. My advice is simple: stay curious, admit when you’re wrong, and treat every mistake as an opportunity to grow - it is the only way you can improve yourself, and be able to better help your fellow men.

Special thanks to Mr. Stefan Dobrescu.

Image courtesy of Gentlemen’s Order, Romania.

https://www.gentlemens-order.com/

https://www.youtube.com/@Gentlemens-Order/videos