Custom Portrait Styles for Special Occasions

Have you ever wanted to give someone a gift that really means something but didn’t know where to start? Finding the right way to capture big life moments like weddings, anniversaries, or even saying goodbye to someone you love can be hard.

The problem is, photos can sometimes feel too ordinary or forgettable. They don’t always show the heart behind the moment. That’s where custom portraits come in. The right portrait style can turn a memory into a piece of art that lasts forever.

As artist CJ Hendry once said, 

“Art is about feeling something. It’s not just what you see - it’s what you remember.”

In this guide, we’ll walk you through how to choose the perfect portrait style - whether it’s oil, watercolor, pencil, or digital - for different special occasions in your life. Let’s make your moments unforgettable.

Key Takeaways

• Different occasions call for different portrait styles - choose based on the mood and emotional tone of the event.

• Oil paintings work best for timeless, formal moments like weddings and memorials.

• Watercolors are soft and romantic - ideal for weddings, birthdays, or joyful celebrations.

• Pencil sketches offer simplicity and emotion, great for intimate moments like anniversaries or tributes.

• Digital portraits are modern, flexible, and perfect for fun, creative gifts or quick turnarounds.

• Communication with the artist is key - share the occasion, reference photos, and your vision clearly to get a portrait that truly feels personal.

• Where you display the portrait matters - at home, at events, or as a gift, presentation enhances emotional impact.

• Proper care and framing preserve the artwork’s quality and meaning for years to come.

  
   

Why Portrait Style Matters for Special Occasions

Every big moment in life tells a story - and the way you choose to capture it can shape how that story is remembered. The style of a portrait isn’t just about looks. It’s about emotion, meaning, and memory.

An oil painting might bring a classic, timeless feel that suits a wedding day. A pencil sketch might feel soft and personal, perfect for remembering a loved one. Watercolor can bring lightness and warmth to joyful milestones. Digital art allows for creativity and fun - ideal for modern celebrations.

Choosing the right portrait style helps you match the tone of the moment. It adds depth to your memories and turns a simple image into something truly special - something worth passing down or putting on display.

Whether you’re celebrating love, honoring a life, or marking a major milestone, the style you choose helps tell your story the right way.

Choosing the Right Portrait Style by Occasion

Every life event has its own energy - and the portrait you choose should reflect that. A bold oil painting might be perfect for a wedding, while a soft pencil sketch may feel more fitting for a quiet remembrance. Picking the right style isn’t just about how it looks. It’s about how it feels.

To make your decision easier, here’s a quick guide that matches portrait styles with different occasions, so you can find the one that tells your story best.

Comparing Portrait Styles – What to Know Before You Choose

Not all portraits are created equal. Some feel classic and serious, others feel soft and sentimental, and some are bold and modern. Each style has its own voice, and choosing the right one depends on the story you want to tell. Let’s break down what each style brings to the table.

Oil Paintings – Classic and Full of Emotion

Oil portraits have a rich, timeless quality that never goes out of style. They’re known for their depth, texture, and warmth, making them perfect for meaningful, formal occasions like weddings or memorials. This style adds weight and dignity to any image, which is why many families treat oil paintings as heirlooms. The downside? They take longer to create and usually cost more - but the final result is worth it if you're looking for something truly lasting.

Watercolor – Soft, Dreamy, and Romantic

If you're drawn to gentle brushstrokes and subtle colors, watercolor might be the perfect choice. This style feels light and emotional, often with a whimsical touch that fits beautifully with romantic moments like weddings or joyful celebrations like birthdays. It’s not meant for high detail, but that’s part of the charm - watercolors capture feeling more than precision. They're especially great for portraits that are meant to feel warm, natural, and a little artistic.

Pencil Sketches – Quiet, Personal, and Honest

There’s something deeply moving about a pencil sketch. Stripped of color, the focus shifts entirely to expression, form, and feeling. Pencil portraits are ideal for more intimate occasions like anniversaries or memorial tributes. They feel thoughtful and sincere - simple in appearance, but full of emotion. Plus, the black-and-white aesthetic works beautifully for minimalist spaces or classic framing. If you're looking for subtle elegance, this is it.

Digital Art – Modern, Bold, and Customizable

Digital portraits are fun, fast, and full of possibilities. Whether you want bright colors, clean lines, or custom backgrounds, digital art gives you endless options. It’s a great fit for birthdays, graduations, or casual gifting. Especially if you’re on a tight deadline or looking for something playful and unique. These portraits are easy to share on social media, print on different materials, or even use as profile pictures. Just know they don’t have the texture or physical feel of traditional artwork.

Working with an Artist – What to Communicate

The magic of a custom portrait doesn’t come from the art alone, it comes from the story behind it. That’s why working closely with your artist is so important. The clearer your communication, the more likely you are to get a piece that feels exactly right. Here’s how to guide the process from start to finish. 

Step 1: Explain the Occasion

Start by letting your artist know why you're commissioning the portrait. The meaning behind it influences everything - from the style and color choices to the mood of the final piece. Is it a romantic wedding gift? A quiet tribute for a memorial? A fun digital portrait for a milestone birthday? The occasion gives the artist emotional context, which helps them bring the right feeling into the artwork.

If it’s for a gift, also let them know the recipient’s personality - are they more classic and traditional, or fun and quirky? That can affect everything from pose to background.

Step 2: Share Details About the Person or Moment

This is where you make the portrait personal. Share a little backstory - what makes this person special? What memory or vibe do you want the portrait to capture? Some people want a more realistic portrait, while others prefer something more symbolic or stylized.

For example:

• “This is my parents' 40th anniversary. They met at the beach, so I’d love if that could be subtly worked into the background.”
• “This is my sister’s graduation. She’s holding her degree, but could you also include her dog in the corner? He was with her through all her college years.”

These small details make a big emotional difference.

Step 3: Send Reference Photos (and Be Specific)

Good reference photos are essential - especially for realism. Send at least 2–3 high-quality images, preferably with different angles and expressions. Here is a guide on how to choose the best picture for your custom painting you can check. 
Tell the artist what you like in each photo. For example:

• “I love the smile in this one.”
• “This lighting feels really warm - I’d like to keep that tone.”
• “Please don’t use this one for the face, it’s not very flattering.”

If the person is no longer living or you only have old or low-res photos, explain that upfront. Many artists can still work with what you have - they may just need more time or direction.

Step 4: Be Honest About What You Want (and Don’t Want)

A lot of people feel shy about giving direction to an artist - but you should. Artists want to know your likes and dislikes so they can create something you’ll love.

Be open about:

• Color preferences (e.g., warm vs. cool tones)
• Painting style (If you still have not decided on painting style check this article)  
• Framing style (headshot, half-body, full-body)
• Background ideas (plain, abstract, meaningful setting)
• Level of realism or stylization
• Any features to avoid or downplay (like if someone’s self-conscious about a certain feature)

Also, if you’ve seen the artist’s past work and loved a specific piece, send it! Saying “I really like how you did the soft background here” is super helpful.

Step 5: Set a Clear Timeline

Many people forget this step, but it matters a lot. Artists usually work on multiple projects at once, and traditional mediums like oil or watercolor take longer to dry and frame. Let them know if you have a hard deadline - like a wedding date or memorial service - and ideally give some buffer time.

Ask about their process too,

• How long do they take to sketch?
• Will you get to review and approve a draft?
• Do they offer revisions?

Understanding their workflow helps avoid stress and miscommunication later.

Bonus Tip: Ask About Delivery & Display Options

If you’re ordering a physical piece, check if the artist handles printing, framing, or shipping - or if you’ll need to take care of that separately. For digital portraits, ask for the right file formats so you can print them clearly at your preferred size.

With these steps, you’re not just placing an order - you’re collaborating. A thoughtful portrait takes care, communication, and a little bit of heart on both sides. When done right, the result is more than just art - it’s a story made visible.

Where and How to Display Your Custom Portrait

Once your custom portrait is complete, the final step is choosing how - and where - to display it. This decision is more than just practical; it’s a chance to give your artwork the presence and meaning it deserves in your space or event.

In the Home – Make It a Focal Point

A well-placed portrait can become the emotional centerpiece of a room. For formal oil or pencil portraits, consider hanging them in spaces that feel personal yet visible - like a living room, hallway gallery wall, or above a fireplace. Watercolor and digital pieces may feel more relaxed and fit beautifully in bedrooms, entryways, or home offices.

Tip: If the portrait is part of a milestone (like an anniversary), consider placing it near other mementos - like framed letters, photos, or keepsakes from that day.

At Events – Add a Personal Touch

For weddings, memorials, graduations, or milestone parties, displaying the portrait at the event adds a personal, emotional element. Place it near the welcome table, gift station, or guest book. Use an easel or elegant frame to elevate the piece and make it part of the décor.

Some families even set up a mini “memory corner” with the portrait, candles, and flowers to honor a loved one during memorials or special celebrations.

As a Gift – Presentation Matters

If you're giving a portrait as a gift, how you present it adds to the experience. Choose a high-quality frame that suits the style of the artwork, and consider wrapping it carefully with a note explaining the meaning behind it. For digital portraits, you can print them on canvas, wood, or even turn them into keepsake items like calendars or cards.

Online & Social Media – Share the Story

Digital portraits especially shine on social platforms. Share the portrait along with a short story or dedication, and tag the artist if possible - it’s a nice way to show appreciation and support their work. Some artists even offer social media-ready versions with your chosen caption or date.

Don’t Forget: Proper Care

• Oil paintings should be kept away from direct sunlight and moisture. Frame them with glass only if needed (some prefer them without).
• Watercolors and pencil sketches are delicate - use UV-protective glass if you’re framing them.
• Digital prints can be reprinted if damaged, but still benefit from proper framing and storage.
• Avoid extreme temperature changes or humid environments (like bathrooms) for any physical piece.

No matter how you choose to display it, a custom portrait should feel like part of your space - something you see often, that reminds you of someone or something you love.

Conclusion

Every life event tells a story. A custom portrait doesn’t just capture how someone looks - it captures who they are in that moment, and what that moment meant. Whether it’s a wedding day, an anniversary, a celebration of life, or a personal milestone, choosing the right portrait style adds emotional depth that lasts long after the moment has passed.

So take the time to pick a style that feels right. Think about the mood of the occasion, how you want it to be remembered, and the kind of emotion you want to carry into the future. Whether it’s the softness of watercolor, the timeless feel of oil, the intimacy of pencil, or the modern boldness of digital - each one tells your story in a different way.

As contemporary artist Kadir Nelson said,

“Art is a language that speaks directly to the heart.”

And the right portrait? It speaks volumes - without saying a word.