The Ultimate Gentleman’s Bucket List: 30 Amazing Experiences

As a way to orient big goals and major accomplishments, a lot of people find it not just useful but also inspirational to create a bucket list. Really, it’s all about the things you’d like to see, accomplish, and experience before you kick the bucket. As a classic men’s style channel, of course, our bucket list skews much more heavily on the menswear and classic style side. 

Somebody said it was a good idea to provide some inspiration for you, in case you haven’t finished your bucket list or just want to add to it. Of course, if you haven’t started, this is a great time. I’ll focus on self-improvement, travel, the finer things in life, and of course, clothing. Don’t worry, we have lots of other suggestions before you go to that big changing room in the sky. 

Of course, these are just suggestions that we hope to inspire you to create your very own bucket list

30 Amazing Experiences: Sartorialism

So, without further ado, our first suggestions, of course, are all from the sartorial world. Shouldn’t be too surprising.

1. Commission a bespoke item of clothing.

It can be a suit, a shirt, a pair of shoes, or all of the above. No, we’re not saying once you go bespoke, you’ll never go back, and only bespoke is the Holy Grail. I’ve bespoke items, and I still buy vintage items for five bucks at the flea market. They’re not mutually exclusive.

In my mind, bespoke clothing is the ultimate expression of your personal style in menswear. It is your chance to manifest your imagination together with another individual to create something that is truly unique to you in either fit, style, comfort, or all of the above.

If you’re a clotheshorse like me, chances are you really enjoy that process of creating something very special where the sky is the limit. If you think everything bespoke is expensive, you can get a smaller item, such as a bespoke watch strap, or a bespoke shirt, and if you want to learn more about the differences between ready-to-wear, made-to-measure, and bespoke, we got you covered.

2. Develop your own statement piece.

If you’re into classic style these days, you stand out in the crowd. I mean, even if you wear a navy blazer, you’re probably better dressed than 90% of the people around you. But, I think a bit more personality to your look is definitely something that can work in your favor.

Let’s say you’re at a trade show and you are a bow tie guy, or maybe you are the green suit guy. It’s definitely something that will help you define yourself as a person, and people will recognize you for it.

You’ve probably seen other people regularly employing a particular color; often, it’s like white or black, but there are other colors that you can use that are maybe your favorite. Yours could mean that you wear something more generic in a particular way. Just think about Gianni Agnelli and how he wore his wristwatch on top of his cuff, right? We all wear wristwatches, we all wear dress, shirts, but people did not wear them in that way.

Or maybe you want to revive vintage accessories because you like collar bars and collar clips, and you decide to wear those. Maybe it’s colorful socks, or do you wear cufflinks all the time? Really, whatever it is that reflects your style.

No, it’s not like a uniform, and you don’t have to wear it all the time. But, statement pieces really help to make your look one-of-a-kind. Like David Byrne’s ensemble in the music video for “Once in a Lifetime.”

3. Visit a famous menswear destination (or all of them!).

Just think of London’s Savile Row or Jermyn Street. You will probably enjoy just strolling around, going into the shops, and seeing what the myth is all about; or heading to Milan’s famous Via Gesu, or you just walk a back street there and maybe find a cool shirtmaker, or Tokyo’s Ginza District; or you go to Naples and try to explore the different tailoring houses, maybe London House, Marinella, and so forth.

4. Build your ideal classic wardrobe.

I know that’s a bit of a moving target because style is always evolving and never stands still. Some people say great clothing collections are never finished, just abandoned. That being said, I personally aspire to have a complete wardrobe. So, I try to have a White Tie ensemble, a Black Tie ensemble, an evening overcoat, a hunting suit, and so forth.

Of course, as I find new things and my style evolves, I may exchange certain things, or I’ll just get more things until my closet can’t take it anymore. No, if you take an organized approach, it doesn’t take a lifetime to acquire your ideal classic wardrobe, but it is a lot of fun to do it over a lifetime – at least, in my opinion. Now, having a wardrobe that is quality, versatile, seasonal, and stylish is definitely something that we strive to help you with here at the Gentleman’s Gazette.

5. Assemble a full Black Tie and White Tie ensemble.

A major step is to have a full Black Tie outfit because it requires special things such as a tuxedo shirt, probably with shirt studs and cufflinks. Chances are you don’t have any other shirts with shirt studs. Maybe you want a detachable collar. Maybe you want a soft, turn-down collar. But you probably will have special Black Tie socks, a boutonniere, and so forth.

Honestly, we talk extensively about these things in our Black Tie guide, which is the most comprehensive in the world. So, just check that one out. And once you’ve mastered Black Tie, you can move on to White Tie, which in my mind, is a lot of fun, even though I don’t wear it very often.

6. Attend a major men’s fashion event.

Probably the biggest one right now is Pitti Uomo in Florence, which happens twice a year – once in January, once in June. If you don’t like the heat, I suggest you go in January. Of course, you can also go to New York Fashion Week, London Fashion Week, or Milan Fashion Week.

But, personally, I’m not too enticed by these events, which is why we decided that we host our very own Belvedere Bash event, which is for classic style enthusiasts. We’ll host in Minneapolis, our hometown, on October 27th and 28th of 2023. Stay tuned, and I’ll hope to see you there! And yes, you can wear your Black Tie and White Tie outfits because that’s what we’re all about. And yes, Preston is going to sing.

7. Invest in a quality piece of heirloom jewelry.

What do I mean by that? Well, something that wasn’t factory-made, but was maybe made bespoke for you or for someone else that is really quality, that is unique, and that will stand the test of time, that you can hand down to your kids and grandkids, and that you enjoy wearing every day.

Jewelry is very personal. Some people may like cufflinks, I just hate them. It can be a watch, it can be a signet ring, it can be whatever other people like to wear, a collar bar, or something more unique such as an earring, or something else that really speaks to you and reflects who you are. Of course, the great thing about it is: it’ll keep your memory alive long after you kick the bucket. And while you’re still kicking, you can enjoy, too.

It’s not about the price. And if you can afford a bespoke piece with a jeweler that resonates with you, that’s awesome. But maybe you find a ring at a flea market that really speaks to you, that fits you, and that’s exactly what you’ve always been looking for, and that’s fine, too. All that matters is that it resonates with you and your style.

8. Own a leather good that you can pass on to someone else.

This goes in a similar vein. Exceptional quality leather that is well cared for and not just left in the sun to rot under UV radiation can last a lifetime. Think about maybe a piece of luggage, maybe a weekender bag, a briefcase, or an attache case. Because chances are that your wallet that you wear every day heavily is probably not gonna last a hundred years. Why? Well, leather is a natural material, and it just wears out.

So, having a leather good that uses a thicker leather rather than a split leather or a leather that hasn’t been split so it’s very thin will probably be the way to go on this one. I mean, don’t you want something that your kids fight over when you’re gone?

9. Shop at an iconic menswear flagship store of a brand that you really enjoy.

As a regular, you’ll already know, we’re not big into labels and all about quality and style. That being said, flagship stores often have a lot of money put into them to create a cool experience. And at the end of the day, experience is something we all strive for. I always find that making a pilgrimage to a flagship store is almost like going to a cool museum with stuff that you’re really interested in. And of course, you go shopping, too. So, it’s all rolled into one thing.

So, food for thought could be the Cartier flagship store at the Champs-Elysees in Paris, or for example, Brioni’s Via dei Condotti  Boutique, or maybe Henry Poole & Co. on Savile Row, or the Ralph Lauren Rhinelander Mansion in New York. And hey, while you’re there, check out Paul Stewart, Brooks Brothers, and J. Press. I’m sure you’ll enjoy it. Basically, in every city, you can find great stores. Just think about Vienna, where you can go to Jungmann & Neffe, which is a great selection of accessories with their art deco interior.

Now that I think about it, we could almost create a list of all the menswear destinations one could travel to. Let us know in the comments if that’s something you’d be interested in.

10. Host a Black Tie event.

If you feel like us, there are not enough opportunities to wear Black Tie. Whenever I talk to other men, that’s definitely something I hear a lot. So, don’t just wait for others to invite you to a party,  just post your own. And the cool thing about it is: people usually love it, and they probably get inspired by you to host their own party, which they likely will invite you to their party, then. So, you get to wear your tuxedo more often.

Be the change you want to see. Yes, you could have a major birthday party and have a Black Tie dress code. You can have a nice dinner party, just a general party, or frankly, you don’t need any particular reason. You can just do it because you love it. Just give yourself permission to do it. I promise you, you won’t regret it.

Frankly, I also think being a host and having to think everything through, also makes you a more desirable guest because you’re probably going to be more respectful. For example, Jack on our team had a Black Tie dress code for his 30th birthday, even though his family and surroundings are not really into menswear. But, it was his birthday after all, so he just went with it and he loved it.

11. Attend or host at least one White Tie event.

A lot of people think of White Tie as something that’s a bit archaic or something that’s not worth investing their money in. If you have your Black Tie wardrobe covered and you want to do something special, I highly recommend it.

Scoring an invitation to a White Tie event is really hard, and unless you’re in Vienna, you go to the Opera ball, or you’re getting a Nobel Prize and attend a ceremony, chances are you probably won’t encounter too many events. If you do, good for you. If you don’t, just host your own. Maybe get together with some others, make it a nice dance party, organize something, invest in it, and I’m sure you’ll have a wonderful time.

12. Find your menswear Holy Grail.

What do we mean by that? Well, find something that’s very evocative of your personal style. Maybe it can be something like a genuine, silk plush top hat, or a grey top hat that you wear when you go to Royal Ascot, or maybe it could be a vintage flight jacket, or maybe even an overcoat that works with your Black Tie outfit. Really, it’s just something that is rare and unique that uniquely suits you and your style.

13. Become comfortable with your personal style.

Yes, I know it’s a broad one, but it’s an important one. Even the nicest clothes that fit well are somewhat useless if you don’t feel comfortable and confident in them, and it’ll show in the way you show up, the way you walk, and the way you present your body.

For example, early on, I was uncomfortable wearing bow ties because I felt it wasn’t me. Over time, I was able to build up the courage, I would put on a bow tie with regular day wear, and all of a sudden, I became more comfortable. Yes, in the beginning, it can be hard – other people may laugh at you or make fun of you. But, over time, you’ll develop the courage to stand above that because that is truly who you are and how you want to be seen.

Today, I don’t wear a bow tie every day and that’s okay, but when I do, I’m really comfortable in my skin and compliments fly to me left and right. If you’re curious about how to take a compliment like a gentleman, check out this video here.

Lifestyle

Next up, we’ll cover experiences relating to lifestyle.

14. Buy an original piece of art or something that just resonates with you.

Lately, for example, I’ve been interested in large-scale vintage menswear posters that were used for advertising. And yes, you can get the reprints, or you can get an original that is linen-backed. And when you frame it, it’s quite impressive. We even have one at the office. 

15. Sample a bottle of something that is older than you are.

The beauty of it is that you can just keep doing that for a very long time. Nothing quite puts your life into perspective as much as sipping on maybe a whiskey or a port that is quite a bit older than yourself. No, it doesn’t have to be something alcoholic necessarily. You can probably find a bottle of Coke that is older than you. It just may not taste as well.

It’s also fun to do, like a tasting, for example. I like port, and so you can go back, and while there’s not always a vintage of the birth year because they only make vintages in certain years, you can definitely find something that is older than you.

16. Play a hand of baccarat at a classic casino.

Originally, James Bond’s game of choice was baccarat. If you prefer poker, go for it, but I think it has something special to play that old game. I mean, what better to live life to the fullest, 007-style?

I’m not talking about some back alley casino, but something like that’s more luxurious and sophisticated. Think of the casino in Monte Carlo or the one in Baden-Baden, which Marlene Dietrich once called “the most beautiful casino in the world.” Of course, if you’re drawn to places like Vegas, maybe check out the Cosmopolitan or Macau’s Grand Lisboa.

One of our writers recently checked this off his bucket list, and he said that he never looked more stylish, felt more refined, and like he was living more glamorously than at this moment while he was also losing 200 euros in a very short amount of time.

17. Eat at a Michelin-starred restaurant.

Even if you’re not into food, having this experience at least once in your lifetime will make you a more complete human being. Among the famous restaurants, there are differences, too. Some are more experimental, some are more classic, so choose whatever floats your boat. Yes, I know not all areas in the world have Michelin-star restaurants because the local tourism board decided not to sponsor the guides coming in. For example, the Midwest of the US is such an area. But, you can still find exceptionally great restaurants that would easily get a star or two or maybe more if they were in other places of the world.

Yes, you’ve probably heard of Noma in Copenhagen, and they may not always be open, there is Central in Lima, there’s Piazza Duomo in Alba in Italy, or The Fat Duck in Bray, England. There’s also The French Laundry in California, and there’s a whole list of the hundred best restaurants in the world. I’m sure you’ll find something that you’re somewhat close to, that you might enjoy.

18. Leave a tip that is larger than your bill.

No, I’m not talking about buying that scone and leaving a five-buck tip. But, maybe after enjoying a hearty meal, you feel inclined to spread the wealth around. A great way to do that is to tip generously. A riff on that is to pay for someone else’s meal at an expensive restaurant. Maybe it’ll inspire them to do like-minded things, but at least, they will think about what just happened.

19. Leave a legacy donation to a charity of your choice.

To maximize the warm and fuzzies, consider leaving a sizable chunk of your inheritance (if there is one) to a charity that deserves it in your mind. That means, you’re not just doing good, but you actually leave a legacy that will be doing good when you’re already gone. Isn’t that cool? Next,

Travel

Of course, going out to see the world is a great thing to do, so experiences relating to travel is what we’ll cover next.

20. Take a classically-inspired trip.

What that means is up to you, of course. You can revive the glitz and glamor of the 1930s. You can go stay at The Ritz in London or in Paris, or maybe you just want to travel aboard The Orient Express. Of course, there are also other trains like The Indian Explorer or The Rocky Mountaineer, or you can take one in India. Or you want to go on an old-school cruise. Maybe like Cunard line Queen Mary, or if you want to go on a Nile cruise on an old steamship that Hercule Poirot was on in “Murder on the Nile.

21. Attend an arts event in a famous venue.

Arts can be enjoyed anywhere, but there’s something special about enjoying them in a place of significance that is just beautiful. And now, it doesn’t have to be the MET Gala, it can be a performance of Shakespeare in the genuine Globe Theater or an opera at the famous La Scala building in Milan, or maybe a classic music concerto at the Elbphilharmonie in Hamburg. If you haven’t heard about that one, take a look at how stunning this building is.

You could maybe go to a dance recital in India at the Kerala Kathakali Center. Nothing beats a setting as sensational as a spectacle itself. I mean, just think about it, seeing Preston perform at Carnegie Hall, wouldn’t that be awesome?

22. Participate in or attend at least one big cultural event.

Think about something fun and exceptional, maybe in a faraway place – like the Running of the Bulls in Pamplona, Spain, or the Tomato Throwing Festival in Italy, or join the parades in Kenya’s Mombasa Carnival, or go to the carnival in Rio de Janeiro, Brazil or strip down naked for the Hadaka Matsuri Festival, the Naked Man Festival in Japan, or you could plan on a tour to the Seven Wonders of the Modern World.

So far, I checked the three from the list. I’ve been to the Great Wall, the Coliseum, and the Corcovado or the Christ the Redeemer statue in Rio. Of course, there’s other things like the Terracotta Warriors or Antelope Canyon, and there are national parks.

There’s so many things in the world that are worth seeing. If you’re not quite sure where to travel, the book “Thousand Places To See Before You Die” provides great bucket list inspiration.

23. Participate in or observe a singular sporting experience.

For example, you can enjoy the great outdoors and go fly fishing in Montana, or maybe deep sea fishing in South Africa or Alaska, or going for a shoot in the Scottish Highlands, or go on to an African safari. Maybe go horseback riding in Montana, Mongolia, or Australia. Maybe for you, it means to compete in a marathon or an Iron Man. I mean, it sure beats riding on your Peloton at home.

If you rather observe than participate, maybe go to a major event like a World Cup soccer game, for example, or maybe a Formula One race in Monaco or elsewhere. And if you’re in a VIP rank, the Moto GP, you may even go on a lap with a pro driver. Now, that’s an experience.

Of course, as a menswear enthusiast, attending the Kentucky Derby or the Royal Ascot horse race in England are definitely high on the list. If you need a refresher on the type of Morning Wear you have to wear there, check out our guide.

Self Improvement

Let’s switch over to more personal or self-improvement things.

24. Devise a personal motto.

Or maybe come up with some core values for you that you live and abide by. It could be something like “best foot forward” or the classically inspired “per aspera ad astra.” A personal model can help guide your life and conduct, even in situations when it gets tough. If you’re not quite sure how to find your motto, I suggest thinking about things that you regret in life because they’re typically close related to the things that you value the most.

Once you have one, you can maybe emblemize it on your letterhead, or you can just quietly have it stitched into your bespoke shirt or your bespoke shoes. Whatever floats your boat. Or maybe you come up with certain core values that you stand by.

Personally, for example, for me, it’s like a quality. I’d rather buy something that is quality and well-made, and it’s maybe used, than buy something new that is just of crappy quality.

We know what values we have at the Gentleman’s Gazette, but I’d be curious to see what you think our values are, or if you think a particular motto that you come up with would suit us quite well. Looking forward to seeing what you come up with in the comments.

25. Learn at least the basics of another language that is not your mother tongue.

I mean, there is a wide, wonderful world of menswear out there, and being able to speak maybe some Italian or Korean, or Japanese will definitely help you to enjoy that even more. In addition, there’s also quite a humbling aspect of learning and speaking another language because you realize that you can’t express yourself in the way you would really want to. Trust me, I should know. I started learning in school, and it’s quite fun to see the personal journey in the language and how your accent evolves, and it is definitely very satisfying.

26. Grow out your hair or facial hair just to see what it looks like.

And hey, once you decide it’s time to maybe shave or go back again, you can also have some fun and come up with cool haircuts like a mullet or different beard varieties just to see what it would be like. 

For example, Preston did that, and it’s a pretty cool progression to see him with these different beard styles. Not sure how to grow a beard? We got a guide where Kyle shares great tips.

27. Learn how to cook a signature dish.

Breaking bread and having a meal together with people is just a very special form of enjoyment. And no, it’s not just about getting the nutrients into your system, but it’s about the connection you create and the memories.

Having a dish that is maybe a little bit special in the way it’s prepared or the way it tastes and that it’s not something that people will find everywhere all the time can really help to almost create kind of a pilgrimage to your place where you host people and share your love for that meal.

Maybe you’re inspired by a meal that you had at a Michelin-starred restaurant, or maybe you’re from a country where there’s a special dish that people where you now live normally don’t know. It is really a gift that you can bring to the world, and people will love to pilgrim to your place where you host them and share your gift with them.

Not sure what to cook? It could be something like a souffle or a Baked Alaska or, for example, we like to do nice beef Wellington dinners. And when it comes out, and you carve it open, it is just always beautiful, and people really love it. And hey, if you invite me to one of your sick traditional dinner parties, I will try my best to get there.

28. Develop your personal variation on a signature cocktail.

Or maybe come up with your own cocktail recipes! Now, during 2020 and 2021, I started experimenting with cocktails and understood what elements you have to add, and I came up with a bunch of nice drinks so that when we have people over, I can ask them, “What do you typically like?” I can present them with something that is in that vein but it’s a bit special.

So, for example, if someone likes a Manhattan, maybe I’ll make a Galliano Manhattan, which is slightly different but in that same family. So, I know they’ll like it even though they’re like, “Oh, I’ve never had that before!”

Or, for example, if someone’s into gin, I have this German Waldmeister syrup, which translates to “forest master,” and it’s like an herbal syrup that I mix with Cointreau, which is an orange liquor, and some lime juice, and people always love it. And this is a vibrant green color, so they’re always like stunned, like, “Wow! This looks like at a restaurant or a bar!”

After you’ve mastered your drink, it’s time for a toast, which leads us nicely to our next item.

29. Learn how to give a great toast.

Speaking in front of a crowd may not be your thing, but frankly, once you learn how to incorporate humor into everything and how to say what you want to say in a non-boring way, it gives you a really nice feeling, and people will appreciate you for it.

We’re not all born as eloquent as Laurence Olivier, and we may not all have the wit of Noël Coward, but it’s definitely something that you can practice and learn and get better. From festivities at the pub to wedding receptions, there will always be an opportunity for you to show that skill, or maybe you have to give a best man’s speech.

By the way, we have a great guide of what to say and what not to say when it comes to those.

30. Make your very own bucket list.

I hope we provided some good inspiration from you here. And don’t feel intimidated. Some things may resonate with you, others won’t, right? Maybe you want to drive a supercar, maybe you don’t.

Make it your own, but as long as you start making it, you think about it, and you keep it in a place where you can always refine it, change it, or add things, and then intentionally cross things off, I firmly believe that once you put down your thoughts, desires, and goals on paper, you work on them, you refine them, you exchange things, you will live a more fulfilled, a more happy, and a more grateful life.

I really look forward to learn what you put on your bucket list. So, please share in the comments below because I’m sure I can pick up some things from you.

Outfit Rundown

Today, I’m wearing a terracotta-white-striped shirt from Spier & MacKay. I’m wearing a Fort Belvedere prototype travel blazer in a fabric that we had woven just for us. It’s a really nice and soft, silk and wool blend that is very breathable and stylish patch pockets. So stay tuned for it.

My pocket square is a silk wool blend from Fort Belvedere. It was inspired by a ceiling at a Viennese museum. My pants are some prototype chinos. I’m currently testing some fabric, and I want to see how it wears right out of the washing machine without ironing it. So, you see some wrinkles, that’s the reason why. After all, if we sell you pants, we don’t want you to spend time ironing them. We want them to look as great as possible once they come out of the dryer or the washer.

My socks are green and brown, shadow stripe from Fort Belvedere, and they transition to my shoes, which were the product of my bespoke collaboration with Amara Hark Weber, and you can find the entire series of how these were made.

Last but not least, two accessories. I have a green precision watch that is very flat with a brown lizard strap, as well as a gold ring with some art deco-inspired carving and an orange stone.

Honestly, I don’t even know what it is, but it works well with my shirt stripe. Amara made me a matching belt of the same leather as the shoes with a gold Fort Belvedere buckle that is exchangeable, and it matches, in this case, my watch and my ring.