Why Your First Portraits Look Weird (And Why That’s Good): The Brutal Truth About Drawing Faces, Fails, and Finding Your Style
If you want to test your courage as an artist, try drawing a face—especially someone you know. Nothing, and I mean nothing, exposes your insecurities, your weird tics, and your lack of patience like staring down the human head. Doesn’t matter if it’s your little sister, your neighbor, or the mugshot you found in the newspaper. You’re gonna screw it up. Their nose will drift, their eyes will stare in opposite directions, their mouth will look like they’ve just had dental work in a war zone. And here’s the punchline: That’s a gift, not a curse.
Confession: My First Portraits Looked Like Uncanny Valley Horror
When I started, every single face came out crooked, bug-eyed, or haunted. My mother’s portrait looked like it belonged in a Tim Burton film. My self-portrait had one ear and three chins. Friends laughed. I hid the drawings and swore I’d never try again. But the more I failed, the more I started to see why portraits are the world’s greatest teacher—and why those early disasters are priceless.
Why Are Faces So Freaking Hard?
Your Brain Is a Liar:
Your mind stores a “symbol” of a face—a circle, two dots, a line. But that’s not what’s actually there. Every time you draw from memory, your hand pulls from the cartoon, not the truth.
Everyone Knows a Face:
We’re wired from birth to read faces. If a single eyebrow is off, everyone spots it instantly—even non-artists.
We Fear the “Likeness Test”:
If it doesn’t look just like them, we panic. But “likeness” comes way, way later—first, you have to learn to see shape, light, and proportion.
Step-By-Step: Rust Dawg’s Guide to Surviving the Portrait Purgatory
Step 1: Embrace the Ugly
Don’t hide your first attempts. Pin them up, laugh at them, own them. They’re not failures—they’re records of your vision warping into honesty. The best artists can show you ten years of “freak faces” before they hit gold.
Step 2: Forget the Outline—Draw the Big Shapes
Start by blocking in the head as a big, faceted mass—not an oval or circle. Use angular planes to rough out the brow, cheekbones, jaw, and chin.
Mark the axis: a vertical line down the face, a horizontal for the eyes. These will save you from “sliding features syndrome.”
Don’t draw the eyes first. Place all the features lightly, then adjust. The nose and brow set the tone; the eyes and mouth follow.
Ingredient Hack:
Flip your drawing upside down and check for errors. The weirdness jumps out instantly—crooked eyes, lopsided skull, warped chin. Fix them without mercy.
Step 3: Squint and Shade for Structure, Not Pretty
Faces aren’t made of outlines—they’re made of planes and value. Squint hard, find the big light and shadow blocks, and map them in first.
Shade the shadow side of the nose, under the brow ridge, below the mouth. Leave the highlight bright.
Don’t sweat the details. A “blobby” face with strong structure is better than a perfect line drawing with zero depth.
Why “Weird” Is Actually Gold
It Teaches You to See Mistakes:
Every off-kilter portrait is a crash course in learning where your eyes and hands are lying to you. The more you spot, the faster you improve.
It Builds Grit:
If you survive the “monster phase” and keep drawing, you become fearless. That’s where real growth lives.
It Sets You Free:
Once you accept that everyone’s first hundred faces are ugly, you’ll stop holding back. You’ll take risks, push shadows, bend proportions, and discover your style.
Personal Confession:
Some of my all-time favorite drawings are old, lopsided portraits. They’re honest, they’re funny, and they have a raw power I lost when I started chasing perfection.
The Anatomy of Weird: Where Portraits Go Off the Rails (and Why You Should Push Harder)
Here’s a brutal, blessed fact—every “wrong” feature is a marker on your roadmap. You don’t become good by tracing pretty faces. You get there by screwing up, by redrawing that droopy eye for the fiftieth time, by pushing so hard you snap your pencil, by asking “what the hell is wrong with this mouth?” and then fixing it. Each disaster is a goldmine.
Common Portrait Disasters—and the Secret Wisdom in Every One
1. Wandering Eyes:
You put one pupil too high, or too wide, and suddenly you’re drawing Sid the Sloth. This isn’t failure—this is your chance to master symmetry, to see that the eye sockets tilt, that eyes curve into the skull, not just sit flat.
2. Alien Foreheads and Caveman Jaws:
Weird skulls happen when you don’t map the planes. Practice seeing the “boxiness” of the head, not just an egg shape. Every weird cranium gets you one step closer to real structure.
3. Gumby Mouths:
Mouths that drift or warp are the classic beginner’s curse. Start with the middle line, not the lips. Build from the corners out. Each monster grin is a crash course in proportion.
4. Floating Noses:
If your noses look like stickers, it’s because you drew the outline, not the planes. Study the way the nose connects to the brow and cheek. Each “stuck-on” schnoz is a ticket to understanding volume.
Ingredient Hack: The Mirror Ritual
Draw yourself. Draw yourself again. Ten, twenty, a hundred times. Nothing speeds up learning like staring down your own weirdness. You’ll see mistakes instantly, and you’ll stop fearing them.
How to Learn From the Weird (And Not Run Away Screaming)
Compare your drawing to a reference, but not obsessively.
Look for big shape differences, not little details.
Ask another artist (or brutally honest friend): “What’s off here?” Nine times out of ten, they’ll spot the tilt you missed.
Don’t erase every “wrong” line. Let your process show. Those ghost lines are a roadmap of your growth.
When to Push, When to Start Over
If the foundation is broken (skull shape, eye line), don’t just patch it—start again. Every restart is worth ten corrections.
If it’s just a feature out of place, fix it. Move that eye, redraw the mouth, lift the jaw.
Treat every portrait like a workout—more sweat, more gain.
Personal Confession:
I still draw monster faces on purpose—caricatures, exaggerations, full-on weirdos. They keep my hand loose, my style sharp, and my ego in check. Every time you dare to go weird, you claim new ground for your style.
Dirty Reality: “Likeness” Is the Last Thing to Worry About
Nobody, not even Rembrandt, got it right the first try. Worry less about copying a face perfectly, and more about understanding the forms. When your portraits start to feel solid—even if they look like ogres—you’re on the path.
From Disaster to Style: How Ugly Portraits Forge Unforgettable Art
If you stick with it—keep grinding, keep embracing the mess—you’ll stumble into something the perfectionists never find: your own style. Every “wrong” mouth, every wild nose, every lopsided eye is a fingerprint on your journey. The weirdness doesn’t just fade; it transforms into a personal voice that no algorithm, no AI, no photo reference can touch.
Rituals for Turning Weird Into Wonderful
1. Keep a “Monster Gallery”
Every time you finish a freaky portrait, put it somewhere you can see it. Pin it above your desk. Use it as a page break in your sketchbook. It’ll remind you where you’ve been, and you’ll start to spot patterns—recurring mistakes, but also wild successes.
2. Try Deliberate Exaggeration
If one eye keeps drifting, push it even farther—turn it into a character. Draw caricatures, goblins, or comic faces. Exaggeration teaches you which features matter most for likeness and expression.
3. Study Real Faces—Not Photoshopped Models
Photograph real people: friends, family, strangers at the bus stop. Real faces have asymmetry, wrinkles, scars, and weird proportions. The more you draw from real life, the less “wrong” your portraits will seem.
4. Make It a Game
Challenge yourself to do a 10-minute portrait every day for a month. Don’t erase, don’t stop. By the end, you’ll see a transformation—a slow taming of chaos into something fierce and unmistakable.
Ingredient Hack: Use a Colored Pencil or Marker for Construction Lines
Start with a blue or red pencil for your guidelines. You’ll see the structure better, and your mistakes will be easier to correct when you go over with graphite. Plus, the color peeking through adds energy to the final sketch.
Personal Confession: My Most Honest Work Was Born in the Wreckage
Some of my most “successful” portraits—the ones people wanted to buy, print, or hang—were born in the messiest pages. The personality, the attitude, the grit, all came from mistakes I refused to erase. You only get real, living faces when you let your hand stumble, then fight to pull something out of the wreck.
Dirty Reality: Weird Faces Are the Mark of an Artist Who’s Not Afraid
Anyone can trace. Anyone can copy. Only the brave lean into the awkward phase and draw their way through it. That’s how you build skill, and that’s how you build guts. If you want to get good, you have to get weird.
Final Word: Your Weird Portraits Are the Proof You’re Alive—and Growing
Here’s the unsweetened, unvarnished truth: those early portraits that make you cringe are gold mines, not graveyards. Every lopsided smile, every too-wide forehead, every lost-in-the-wilderness eyeball is a milestone. They’re not just proof you tried—they’re proof you dared. If your work isn’t weird at first, you’re playing it too damn safe.
Confession: My Breakthrough Came When I Stopped Chasing Pretty and Started Chasing Honest
The minute I stopped worrying about perfection and started chasing the raw, honest, ugly truth of every face—that’s when things clicked. Suddenly, every “mistake” became an ingredient. The strangeness became character. The crooked lines turned into attitude and voice.
Ultimate Survival Wisdom: Lean In, Laugh, and Learn
Show your monster portraits to other artists. Trade horror stories, swap advice, and challenge each other to make even weirder faces.
Study the greats—Sargent, Schiele, Alice Neel, Egon Schiele, Lucian Freud. Their early works? Wild, raw, full of “mistakes.” Their masterpieces? Just as weird, but with purpose and punch.
Most of all, remember: the weirder the journey, the more powerful the transformation.
So fill your walls, your sketchbooks, your trash bin with faces that look a little haunted. Every time you draw, you’re one step closer to a likeness that bites back—and a style that nobody else can touch.
See Also:
“Drawing on the Right Side of the Brain” by Betty Edwards (spotting and fixing what’s off)
“Portrait Drawing” by John Singer Sargent (studies and experiments, not just finished pieces)
The “Draw Yourself Every Day” Challenge (document your weirdness, watch it evolve)
James Gurney’s “Sketching People” (faces in the wild, not in the studio)
#uglyportraitclub on Instagram (revel in the raw and real)