A conversation with Michael about tailoring, confidence, and what belongs underneath.

What makes a great suit feel so powerful—and what belongs underneath it?

On a new episode of Brief Talk After Dark, I sit down with Michael Dobbs for a conversation I have wanted to have for a long time: suits and underwear. They may seem like two separate interests, but for many guys, they fit together perfectly.

We talk about what makes a suit sexy, why the ritual of getting dressed can completely change your mindset, and how the underwear no one else can see may be the most important part of the outfit.

Brief Talk After Dark: What makes a great suit feel so powerful—and what belongs underneath it?

A Suit Can Be a Kind of Armor

Michael’s love of suits began when he was about 20 years old and working in Boston. It was the 1990s, when Back Bay was still filled with men in traditional businesswear. Seeing those sharply dressed guys made an impression that never left him.

Today, he describes a suit as much more than formal clothing. It can be a special outfit that changes how you carry yourself, much like leather, sports gear, latex, or puppy gear does for the people who love those styles.

“A suit is almost like armor. Just like leather, sports gear, latex, or puppy gear, it’s a special outfit that changes how you feel. When I put one on, I feel confident, sexy, and ready for whatever comes next.”

The Power of a Suit: A suit is almost like armor

That feeling is something many gear lovers understand. Clothing can create a boundary between everyday life and the version of yourself you want to become. A suit can make you feel polished, focused, powerful, or sexy before you ever walk into a room.

Getting Dressed Is Part of the Experience

A suit is never only the jacket and trousers. The complete look is built one choice at a time: the shirt, tie, cuff links, pocket square, socks, shoes, and everything worn underneath.

For Michael, that process is a ritual. He sometimes wears a suit even while working from home because changing into it signals that the workday has begun. The outfit helps create the mindset.

“Putting on a suit isn’t just getting dressed. It’s choosing the shirt, the tie, the cuff links, the pocket square, the shoes, and even the underwear. Every step is part of a process that helps me feel confident before I walk out the door.”

More Than Just Clothes: Putting on a suit is a process

The same transformation can happen with other types of clothing. Running tights can put you in the mood to exercise. Cowboy boots, jeans, and a hat can bring out a different side of your personality. Leather can unlock another one. What matters is how the clothes make you feel.

Why Suits Remain So Appealing

Workplaces have become much more casual. Offices that once expected jackets and ties now settle for trousers and a shirt—or jeans and a polo. Even in London, with its legendary tailoring tradition, Michael has noticed that complete suits are no longer as common in financial districts.

That may be one reason a fully styled suit feels even more distinctive today.

Michael loves pinstripes, especially as part of a three-piece suit. He appreciates waistcoats, rich fabrics, beautiful linings, cuff links, pocket squares, sheer over-the-calf socks, sock garters, and highly polished shoes. Each detail adds to the energy of the finished look.

“What I love most about suits is the feeling they create. It’s the appearance, the energy, and the confidence. Putting on a suit gives me a sense of power that a lot of people don’t understand unless they’ve experienced clothing that makes them feel incredible.”

Why Suits Are So Appealing: appearance, energy, and confidence

There is also something exciting about going beyond the minimum. If a restaurant requires a jacket and tie, Michael does not want to dress one level above the requirement—he wants to go ten levels above it. Dressing well brings compliments, attention, and, most importantly, personal satisfaction.

The Best Part May Be Underneath

Of course, this is Brief Talk After Dark, so we had to discuss what goes under the suit.

Michael’s two favorite styles are thongs and jockstraps, with thongs taking the top spot most of the time. The contrast is part of the appeal: a traditional, perfectly coordinated suit on the outside and something small, sexy, and unexpected underneath.

“I sneak thongs under my suits all the time. Even with a beautifully lined pair of trousers, I love having that extra layer underneath. It’s part of what makes wearing a suit feel complete.”

Underwear Completes the Experience: thongs under suits

That secret can give you a private confidence boost throughout the day. No one else has to know what you are wearing, but you know—and that can change the entire experience.

There are no rules about the “right” underwear for a suit. A thong, jockstrap, bikini, classic brief, boxer, or something more adventurous can all work. The best choice is whatever makes you feel good in the clothes.

A Lifetime Love of Thongs

Michael has been wearing thongs for more than 30 years. His story began at 16, when he found a hidden package at Kmart and took it home. That first purchase grew into an enduring part of his style and identity.

After stepping away from underwear collecting for a while, he returned to it around 15 years ago. Today, he attends thong events and enjoys discovering new brands and styles through other people in the community.

“I’ve been wearing thongs for more than thirty years. It started with one hidden package from Kmart when I was sixteen, and it’s grown into something that’s become part of who I am.”

A Lifetime Love of Thongs: Michael’s story began with a package from Kmart

The story will sound familiar to many underwear lovers. Before online shopping and social media made nearly every style easy to find, discovering something different in a department store could feel like finding a new world. That first pair was not just underwear—it was the beginning of understanding what made you feel like yourself.

Suits, Underwear, and Wearing What You Love

The biggest lesson from our conversation is simple: wear what makes you feel confident.

For Michael, that might be a pinstripe three-piece suit with a thong underneath. It might be a tuxedo and patent leather shoes, a leather blazer and trousers, compression gear for a run, or cowboy boots worn with a suit. Each look creates its own energy.

You do not have to like every combination, and you do not need everyone else to understand yours. Personal style becomes much more interesting when we stop treating categories as rigid rules and start letting people enjoy what makes them feel good.

So, what belongs under a great suit? Whatever makes you feel sexy, powerful, and ready for whatever comes next.

Listen to Brief Talk After Dark featuring Michael talking suits

Listen and Follow

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Follow Michael on Instagram: @michael_d_living

Are you a suit guy? What do you wear underneath? Send your thoughts to feedback@brieftalkpodcast.com. I would love to hear from more suit lovers—and this conversation definitely deserves a part two.