Ask someone to picture the perfect pin up look and the first thing they'll imagine is almost certainly the hair. Before the red lip. Before the cat eye. Before the polka-dot dress.
The hair.
Specifically: the victory roll. The pin curl. The pompadour. The carefully set wave. These hairstyles are so deeply embedded in the visual language of vintage glamour that they have become shorthand for the entire aesthetic — immediately, unmistakably, gloriously mid-century.
And they are, without question, some of the most spectacular, most technically demanding, and most visually rewarding hairstyles ever devised. When a victory roll is done perfectly — symmetrical, smooth, dramatically high — it transforms not just a hairstyle but a presence. You don't just look different. You look like you belong in a different era, a better-dressed, more deliberately beautiful era, where hair was an art form and every morning was a creative act.
At Pinup Art Studio, we see vintage hairstyles in our customers' reference photos every day — and we know from experience how powerfully a great vintage hairstyle elevates the quality of the resulting custom pin up portrait. In this comprehensive guide, we'll teach you every major vintage pin up hairstyle — from the iconic victory roll to the elegant chignon, from the dramatic pompadour to the soft and romantic pin curl set.
🎀 The Philosophy of Vintage Pin Up Hair
Before diving into specific styles, it's worth understanding the philosophy that underlies all of them.
Volume is virtue 💇♀️ — Vintage pin up hairstyles are not subtle. They take up space. They announce themselves. The higher the victory roll, the more carefully set the curl, the more deliberately architectural the composition — the more authentically vintage the result.
Structure requires support 💪 — Unlike contemporary "natural" styles that rely on the hair's own behavior, vintage styles are constructed. They use setting techniques, supports, and careful assembly to create shapes that hair doesn't naturally achieve. This is not a limitation — it's what makes them spectacular.
The finish is everything ✨ — A vintage hairstyle should look polished and deliberate. The smooth sections between rolls and curls should be genuinely smooth. The set curls should be genuinely set. Half-measures undermine the entire aesthetic.
Tools are essential 🔧 — You cannot create authentic vintage hairstyles with just a brush and a prayer. Setting lotion, bobby pins (many of them), a fine-tooth comb, hot rollers or pin curls, and a strong-hold hairspray are non-negotiable.
🌹 Victory Rolls: The Queen of Vintage Hairstyles
The victory roll is the single most iconic vintage pin up hairstyle — the first thing most people imagine when they think of 1940s–1950s glamour.
What Are Victory Rolls? 🎨
Victory rolls are large, cylindrical rolls of hair positioned above the forehead, on the crown, or along the sides of the head. They create dramatic height and volume, framing the face with architectural confidence.
The origin of the name is somewhat debated, but the most popular theory connects them to WWII victory roll aircraft maneuvers — a romantic piece of wartime mythology that fits the era perfectly.
Types of Victory Rolls 💇♀️
The Classic Double Victory Roll — Two symmetrical rolls positioned above the temples, curving up and inward above the forehead. The most recognizable version — immediately associated with the 1940s pin up aesthetic.
The Single Central Roll — One larger roll centered above the forehead, creating a more dramatic, architectural look.
The Side Rolls — Two rolls positioned at the sides of the head, with hair swept up from each temple. More theatrical and three-dimensional than the classic double roll.
The Crown Roll — A roll positioned at the very top/back of the crown, with the front hair smooth or softly waved. A slightly softer, more accessible version of the full victory roll look.
How to Create Victory Rolls: Step-by-Step 📋
What you need:
- Setting lotion or mousse
- Fine-tooth comb
- Bobby pins (minimum 20 — more for long/thick hair)
- A small cylindrical tool (a round brush handle, a roll of toilet tissue, or a specialized victory roll tool)
- Strong-hold hairspray
Step 1: Section off the hair for your rolls — typically the front 2–3 inches on each side. Clip the remaining hair away from these sections.
Step 2: Apply setting lotion to the roll sections and comb through thoroughly.
Step 3: Take one section and begin rolling it around your cylindrical tool from the ends toward the roots, rolling the hair away from your face and upward.
Step 4: When the roll reaches the desired position (typically touching or very close to the scalp at the temple/front hairline), slide the tool out carefully while holding the roll in place.
Step 5: Secure with bobby pins — at least 4–6 pins per roll, inserted from both sides to create a stable criss-cross structure.
Step 6: Repeat for the second roll, using a mirror or a friend to ensure symmetry.
Step 7: Smooth any visible pins or loose strands with a fine-tooth comb.
Step 8: Spray generously with strong-hold hairspray.
🌀 Pin Curls: Soft, Romantic, and Timeless
Pin curls are the foundation technique of virtually all vintage hairstyling — small sections of hair wound into flat circles and pinned close to the scalp, then dried (either naturally or with heat) to create lasting curl or wave patterns.
The Basic Pin Curl Technique 📋
Step 1: Wash and condition hair. Apply a setting lotion while hair is still damp.
Step 2: Section hair into small sections — the smaller the section, the tighter and more defined the curl.
Step 3: Take one section and wind it into a flat circle against the scalp, winding in the direction you want the finished curl to go.
Step 4: Secure with two bobby pins in a cross pattern.
Step 5: Continue until all hair is pinned.
Step 6: Dry completely — either air dry (2–4 hours) or sit under a hood dryer (45–60 minutes). The hair must be completely dry before removing pins.
Step 7: Remove pins and gently separate curls with fingers (not a brush — a brush disrupts the curl pattern).
Step 8: Style into your desired arrangement and set with hairspray.
Pin Curl Arrangements for Different Results 🎨
All curls in the same direction — Creates a smooth, unified wave pattern when brushed out. The classic 1940s Hollywood wave.
Alternating directions (staggered) — Creates tighter, more bouncy curls when separated.
Spiral arrangement — Creates the specific bouncy ringlet look associated with early 1950s pin up hairstyling.
🎭 The Pompadour: Dramatic Height and Attitude
The pompadour — hair swept dramatically upward and back from the forehead, creating significant height — is the most theatrical of the vintage pin up hairstyles.
Creating a Pin Up Pompadour 📋
Step 1: Section off the front 3–4 inches of hair.
Step 2: Backcomb (tease) this section thoroughly from roots to mid-length — the teasing creates the volume that supports the pompadour height.
Step 3: Smooth the surface of the teased section with a brush, maintaining the volume underneath.
Step 4: Roll or fold the smooth surface over the teased interior and pin securely at the crown.
Step 5: Smooth the sides away from the face and secure.
Step 6: Style the remaining hair as desired — either pinned up, in curls, or in a low arrangement.
🌸 The Veronica Lake Wave: Soft and Seductive
The Veronica Lake wave — named for the 1940s actress famous for her signature peek-a-boo style — creates a smooth, dramatic wave that falls partially over one eye.
Creating the Veronica Lake Look 📋
Step 1: Set hair in large pin curls all rolling in the same direction (away from the face for a classic side-swept wave).
Step 2: Once dry, release and brush out thoroughly into a smooth, unified wave.
Step 3: Use a brush or comb to direct the wave to fall dramatically over one eye — the left side is most traditional.
Step 4: Secure the other side above the ear if desired.
Step 5: Set with strong-hold hairspray.
💫 Quick Vintage Hairstyle Guide for Your Portrait Reference Photo
Not all of these styles are achievable without practice. Here's a quick guide to the vintage hairstyle that best matches your portrait style and your skill level:
| Portrait Style | Recommended Hair | Difficulty |
|---|---|---|
| Classic Pin Up | Victory rolls or pin curls | ⭐⭐⭐ |
| Hollywood Portrait | Veronica Lake wave or elegant updo | ⭐⭐⭐ |
| Rockabilly Portrait | Pompadour or dramatic victory rolls | ⭐⭐⭐⭐ |
| Glam Portrait | Formal updo or dramatic waves | ⭐⭐ |
| Flirty Portrait | High ponytail with a bow or soft curls | ⭐ |
| Beach Portrait | Loose waves or tousled natural style | ⭐ |
❓ Frequently Asked Questions
Q: Do I need to style my hair for my portrait reference photo? Not necessarily — our artists can apply the vintage hairstyle in the portrait regardless of your hair in the reference photo. However, having vintage-styled hair in your reference photo helps the artist understand the look you're going for and creates a more authentic starting point.
Q: What if my hair is too short for victory rolls? Victory rolls can be created in hair as short as chin-length with the right technique. For very short hair, a pompadour or pin curl set in the available length is a great alternative.
Q: Can I achieve these styles without going to a hairdresser? Yes — all of these styles are achievable at home with practice and the right tools. YouTube has excellent tutorials for each style. The key is practice — don't attempt your first victory roll the day you want to take your portrait reference photo.
Q: What products do you recommend? For setting: Lottabody Setting Lotion or Schwarzkopf Osis+ Spray Wax. For hold: Got2b Glued hairspray or Tres Semme Mega Hold. For smoothing: a light pomade or cream applied to the surface only.
🚀 Style Your Hair — Then Commission Your Portrait
You now have everything you need to create one of the most spectacular vintage hairstyles in existence. Practice, play, and find the one that makes you look in the mirror and see a 1950s illustration looking back.
And when that moment comes — take your reference photo and let our artists at Pinup Art Studio do the rest.
👉 Order your custom pin up portrait at Pinup Art Studio today and let us preserve your most spectacular vintage look forever.
💇♀️ Victory rolls. Pin curls. The pompadour. The hair that started it all — and still does. ✨
