Reward Yourself! 8 Buys to Celebrate Milestones & Success

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As we move through life, we happily encounter special occasions and events. These can be commemorated with the purchase of an item to mark the achievement or milestone. Success may be its own best reward, but when celebrating success, don’t forget those important words: treat yourself!

The most personal rewards will become wonderful mementos of the occasion that you’re celebrating. These could include achievements like a big promotion or a new business venture, personal milestones like getting married, buying a home, or major events like a special birthday, or anniversary.

We’re going to provide you with a list of suggested items that fall within the realm of a classic lifestyle. These will be ideal for marking any occasion or accomplishment. We’ve specifically curated this list to include items that you can regularly enjoy, items that stand the test of time, both for usefulness and longevity. It will bring you increasing enjoyment the longer that you use them.

8 Buys to Celebrate Milestones & Success

The gifts on our list aren’t all expensive, but they are specialty items that you wouldn’t consider to be everyday purchases. But when it comes to celebrating the special events in your life, you’re worth it.

Fountain pen paper and a Lamy Safari fountain pen
Fountain pen paper and a Lamy Safari fountain pen

1. A Quality Fountain Pen

According to popular accounts, American author Ernest Hemingway marked his time as an ambulance driver in World War I by purchasing a fountain pen. But, not just any fountain pen, a Montegrappa fountain pen. This is because the factory was near where he was stationed. 

Beautiful pens are traditional gifts, especially for things like academic achievements, like graduating from school or college or starting a career in fields like law, journalism, or writing. But, feel free to follow Hemingway’s guidance and purchase one to celebrate any event you choose.

For instance, you could use your new pen to sign a special document like a mortgage for a new home, a contract for a new job, or certifying a marriage certificate. Every time you use your pen, you’ll remember that special occasion and, contrary to what many people assume, quality fountain pens can be found at any price point.

We offer guides to fit your needs, from budget to mid-range. We also have a guide where Raphael helps you determine if it is worth it to celebrate a special occasion with a Meisterstück. We also have a post that will have you master writing with a fountain pen in no time.

Of course, if you prefer not to write with a fountain pen, many quality manufacturers also offer rollerball varieties of their popular fountain pen models. These are also great alternatives.

oil paintings
Adding some oil paintings will make your space look more polished and formal.

2. Artwork

In 1898, London art collector Asher Wertheimer commissioned celebrated artist John Singer Sargent to paint his portrait for his silver wedding anniversary. Over the next decade, Sargent completed 12 portraits of the Wertheimer family.

We don’t necessarily expect you to accrue enough art to fill the Tape Gallery, but a unique piece of art is a wonderful way to celebrate a worthy achievement or event. This could literally be any kind of work of art of your choosing that has some kind of significance for you.

For instance, following an especially memorable trip, you might purchase a landscape of the place that you visited or have a print shop enlarge a photo that you took and then frame it. You’ll then be reminded of that trip and you’ll also have an interesting conversation piece for guests.

You could associate a famous work of art that you like with your achievement. Maybe after spearheading that big merger at work, you feel like Napoleon crossing the Alps or, perhaps, the birth of a child could be commemorated with the framed pages of a beloved comic book; a comic book that you hope to someday share with your little one.

Any special event is a good opportunity to seek out fine art, whether you do your shopping at the local antique store or a contemporary art gallery.

If your budget allows it, you could even commission an original piece of art like a portrait on a wedding day or a special birthday. While original art is certainly expensive, it is a unique gift and something you will treasure for the rest of your life. But, of course, it’s the memory, not the money that matters.

So, this could be as simple as buying a frame at the store and printing out a picture of yourself to put in it.

Bspoke Split Toe Single Monk Strap Shoe
Bespoke clothing, like bespoke shoes, is a personal reward that can be regularly enjoyed.

3. Bespoke Clothing

To really enjoy regular use of your gift, consider purchasing a bespoke garment to mark a special occasion. Bespoke clothing will emphasize the personal nature of your achievement and it also gives a great feeling of giving back to yourself. After all, you’re watching this channel, so what gift could beat high-quality, perfectly-fitted clothing?

Bespoke clothing can also be tailored to your needs and budget. Looking forward to a major wedding anniversary? You could celebrate with a gorgeous bespoke suit.

Consider commemorating your climb up the corporate ladder with a bespoke pair of shoes. And a bespoke dress shirt is a great gift for any occasion from which you’ll get a lot of use. Consider a bespoke item that you’ll be able to wear often. It’ll remind you of the special occasion and improve the cost per wear ratio.

If it’s your first foray into bespoke garments, we get that it might be confusing, so avail yourself of the guide offering guidance we’ve made here at the Gentleman’s Gazette.

Raphael Prototype with Fort Belvedere Wallets New
Leather accessories, like wallets, are ideal personal rewards.

4. Quality Leather Accessories

Because of leather’s beautiful luster and exceptional durability, leather items are ideal for commemorative gifts. They can suit a variety of occasions and personal styles and will be beloved treasures for a lifetime. We will note for instance that leather is the traditional gift for third-year anniversaries.

A new wallet is a great gift for professional milestones like starting a new job, a big promotion, or completing a major project. But, as far as we’re concerned, anytime is a great time for a new wallet. Need help navigating your options? Check out our guide to wallets.

In a similar vein, consider a business card case, it will elevate your entrepreneurial style and serve the valuable function of protecting your business cards and, you guessed it, we have a definitive guide for business card cases as well. 

For a different span on leather goods, consider investing in a pair of dress gloves to commemorate a unique and unforgettable event like a stroll through a historic garden on a trip abroad, a gala premiere of an opera, supper at the captain’s table during a cruise, or anytime that you want to feel like you’ve stepped outside of a J. C. Leyendecker illustration.

Medium Budget Watches
Whether it’s a Seiko or a Rolex, a wristwatch or a pocket watch, it might be time for you to reward yourself with a luxury watch.

5. A Luxury Watch

For many gentlemen of style, they know they’ve “made it” when they buy their first luxury watch. But, contrary to what you might think, a watch doesn’t have to be expensive to become a treasured keepsake. So long as it’s meaningful to you, it’ll be a wonderful personal reward.

So, while most people associate the iconic Rolex as one of the first purchases made by the newly wealthy, we’ll let you decide whether this watchmaker is for you after you review our “Is It Worth It?” guide on Rolex watches.

If you’re just starting out your collection, you may find our recommended watches under $100 helpful.

Another avenue to consider is secondhand watches. High-quality watches are designed to last several lifetimes, so they’re great items to pick up on the vintage market. You get a quality watch at a fraction of the cost and you may learn that some of these watches already have a story of their own.

Maybe they were the previous owners’ first big personal purchase or you could find an inscription or engraving. This hint added significance to its previous owner. When you buy the watch, you’re directly participating in its storied history and you’re adding your own chapter.

The Jaeger LeCoultre Reverso
The Jaeger LeCoultre Reverso

As with all high-end, secondhand purchases, do your research beforehand to make sure that what you’re paying for is fair. Fortunately, there are many reputable companies that specialize in reselling luxury watches, and they can help you find the perfect new-to-you timepiece.

No matter what your watch costs, you can always get it engraved with a meaningful date or short message. This will immediately elevate it to the heirloom status.

Brown patterned suit and yellow Winchester shirt, orange boutonniere, orange tie and cufflinks from Fort Belvedere
You’ll have lots of opportunities to enjoy, and wear, jewelry as a personal reward.

6. Quality Men’s Jewelry

Jewelry as a gift is usually associated with women, but we don’t think there’s any reason why girls should have all the fun.

As we discussed in our comprehensive overview of men’s jewelry, men have been wearing jewelry for millennia and you have lots of jewelry options when it comes to rewarding yourself, like a class ring to mark the graduation from your beloved alma mater or signet ring to really help you put your stamp on the world.

There are some men’s jewelry types that make great personal rewards. They will elevate your entire look, but they won’t break the bank.

Signet Rings with varying engraving styles
A signet ring is an excellent, personalized reward

Cufflinks are an exceptional personal reward because, provided that you have a French cuffed shirt, you’ll have many opportunities to wear them. It could be fun to associate some aspect of the cufflinks with your achievement. This will help you recall the occasion.

Silver and then, gold cufflinks would be very traditional, but you could also be more creative. Snorkeling on a tropical vacation could be associated with the deep blue of lapis lazuli or the deep green of malachite with a camping trip. So long as the associations make sense to you, you can pick anything that you like.

Eagle Claw Cufflinks with Malachite Balls 925 Sterling Silver Platinum Plated - handmade by master jeweler - Fort Belvedere
Colorful cufflinks can be associated with almost any special occasions or anniversary.

Fort Belvedere offers a variety of cufflinks with many colorful stones. These are able to suit countless occasions. You can also track down unique cufflinks at reduced prices. Try combing through antique stores and vintage websites.

Commemorate finally getting the car of your dreams with Ferrari cufflinks or even a successful trip to Vegas that you mostly, maybe, can’t remember.

Novelty cufflinks like these are fun additions to your wardrobe. They add unique creativity and levity but, for the greatest versatility, they should be unique counterpoints and not your principal pieces. So, we suggest grounding your cufflink collection with foundational pieces.

Monkey Fist Knot Cufflinks from Fort Belvedere
Monkey Fist Knot Cufflinks from Fort Belvedere
Monkey Fist Knot Cufflinks - 925 Sterling Silver Platinum Plated

Fort Belvedere

Monkey Fist Knot Cufflinks – 925 Sterling Silver Platinum Plated

Monkey Fist Knot Cufflinks - 925 Sterling Silver Rose Gold Plated

Fort Belvedere

Monkey Fist Knot Cufflinks – 925 Sterling Silver Rose Gold Plated

Double-sided Monkey Fist Knot Cufflinks - Vermeil Sterling Silver Yellow Gold Plated

Fort Belvedere

Monkey Fist Knot Cufflinks – Vermeil Sterling Silver Yellow Gold Plated

In classic cufflink designs, the most timeless is the monkey’s fist, which has been gracing gentlemen of style for centuries. It’s also available from Fort Belvedere in silver and gold. They’re a great personal gift with which to seed your new cufflink collection.

For something that adds unique visual interest, consider collar jewelry. They add unusual flair to outfits. So, on the special occasions when you want to add a pop to your outfit, you’ll also add a spring to your step when you’re reminded of the special occasion that this jewelry commemorates.

Many examples can be found in vintage shops, but there’s something special in knowing that you’re the first to own a piece of jewelry. The Fort Belvedere shop carries all the primary types of collar jewelry, including bars, pins, and clips. All of which are available at a very reasonable price, and they’ll mean a great deal to a clothes enthusiast.

Collar jewelry can add some visual appeal to your outfit
Collar jewelry can add some visual appeal to your outfit
Collar Bar Clip in Yellow Gold For Classic Narrow Spread Collars

Fort Belvedere

Collar Bar Clip in Yellow Gold For Classic Narrow Spread Collars

Prince of Wales Glen Check Silk Tie In Burgundy And White

Fort Belvedere

Prince of Wales Glen Check Silk Tie in Burgundy and White

Pink Carnation Boutonniere Life Size Lapel Flower

Fort Belvedere

Pink Carnation Boutonniere Life Size Lapel Flower

Finally, what gift for a special occasion is better than something you can wear on special occasions? A beautiful set of studs is the perfect finishing touch for a perfectly put-together formal ensemble that will make you swell with pride at your achievement every time you’re in black or white tie. You can learn more about shirt studs in our definitive guide.

But, we’ll leave you with an important tip for buying: vintage studs are beautiful, but most are sized for old-style shirts. It will often be too small for contemporary evening shirts, so you could find yourself constantly chasing your escaped studs across the dance floor.

Modern day shirt studs and matching cufflinks set by Fort Belvedere
Modern day shirt studs and matching cufflinks set by Fort Belvedere

For perfectly sized shirt studs that are timelessly elegant, look no further than Fort Belvedere. You’ll be the toast of the party in your lovely new studs. And speaking of toasting…

Raphael Schneider holds a bottle and glass of champagne
Consider popping some bottles and toasting yourself as a personal reward.

7. Top-Shelf Alcohol

For those of you who partake, we can think of a few better ways to toast your success than with a good drink. Drinks can be drunk immediately to help set a festive mood or stored away to age for a delightful treat in a few years. When it comes to spirituous celebrations, whiskey, port, brandy, cognac, and champagne are all considered excellent options.

We’ll help you decide if Dom Pérignon is right for you in our guide, but remember that you don’t need a $12,000 bottle of Hennessy Ellipse to celebrate. Although, of course, it doesn’t hurt. 

Raphael recommends St. Hilaire Blanquette de Limoux, an effervescent wine that sparkles like champagne, but at a fraction of the cost. One of our writers treats himself to a bottle of Rémy Martin XO on his birthday. Studying and testing spirits at different price points to find the one that is best for you will make the final gift all the sweeter when you select it.

If you need help, it’s been our experience that the staff at reputable liquor stores are more than happy to share their expertise, and they can also make recommendations. With a little expert help, you’ll be able to resplendently and responsibly enjoy your special beverage on your special occasion.

Cigars might be a great way to reward yourself
Cigars might be a great way to reward yourself

8. Fine Cigars

Passing out cigars is traditionally associated with the birth of children but, if you’re so inclined, we think you can light up to mark any special occasion.

Of course, all tobacco products have certain risks, so consider the circumstances of your own health. By saving cigars for extraordinary occasions, you’ll make savoring the smoke even more special and, ideally, mitigate the impact on your own health.

Cuban cigars are considered the best, but quality cigars don’t have to break the bank or be smuggled past any embargoes. Many cities and towns have local smoke shops, where the staff will be more than happy to introduce you to the basics of cigar smoking, and they can even suggest brands.

Just make sure that you light it in the proper way. Cedar spills or lighters designed for cigars that contain butane are also acceptable.

Conclusion

We hope that you’re excited about some of the gifts that we suggested and you’re booming with new ideas on how to reward yourself.

Outfit Rundown

Kyle wearing wearing a blue cable-knit sweater, a blue and white striped dress shirt, green trousers and brown chukka boots and Fort Belvedere socks.
Kyle wearing wearing a blue cable-knit sweater, a blue and white striped dress shirt, green trousers and brown chukka boots and Fort Belvedere socks.
Dark Brown Two Tone Solid Oxford Socks

FORT BELVEDERE

Dark Brown Two Tone Solid Oxford Socks

Today, I’m wearing a blue cable-knit sweater, a blue and white striped dress shirt, green trousers and brown chukka boots. I’m also wearing a pair of Fort Belvedere socks to round out the outfit.

For the pair of socks I’m wearing, you can take a look at the Fort Belvedere shop here.

Let us know in the comments below some of your favorite brands of the categories that we’ve listed today and share any special gifts that you’ve picked up!

Reader Comments

  1. I would argue for options #9 and #10:

    #9 A nice meal at a great local restaurant. As much others may argue that eating out to celebrate is overdone to the point of being as cliched as the movie/dinner date, I enjoy high quality food and the experience of exposing myself to great new flavours and textures and savouring them altogether makes for a rewarding time.

    #10 Experiences. The list is never ending and it’s something that fosters euphoria in the leaf up and creates a lingering sense of it days, weeks and even months later even after the high of buying something wears off.

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