Theatre Headshots in Little Italy

Headshot Day in Little Italy | Lissa Gray
Lissa Gray headshot in Little Italy

Headshot Day in Little Italy

Three characters, three looks, one afternoon in Little Italy.

My daughter Lissa is graduating with her Theatre degree and needed headshots for auditions — not just a nice photo, but a set that shows real range. In her Auditioning class, she learned that a strong headshot session requires specificity: you don’t just show up and smile. You plan each look around a character type, and you come prepared. So that’s exactly what she did. Lissa chose a specific character for each outfit and built a playlist for each one to get into the right headspace before we started shooting. My sister — who’s also a photographer and has a deep background in theatre — came along, and the three of us headed to Little Italy to knock it all out.

Look One

The Girl Next Door

Denim jacket, striped sundress, soft light. Lissa built this look around the warm, approachable type — the lead in a rom-com, the best friend in a coming-of-age film. The kind of face a casting director sees and immediately thinks “she’s easy to root for.” We found a clean wall and some great greenery nearby and worked both locations.

Lissa in striped sundress, soft smile Lissa peeking through green foliage

Jacket off for a softer take on the same character.

Look Two

The Scene-Stealer

Teal corduroy jumper with embroidered flowers over a cream sweater. Lissa picked this look for the quirky character-actress range — the one who steals every scene she’s in. She had her playlist going and was already in character before we even started shooting.

Lissa in teal jumper against pink wall, playful head tilt Lissa with hand in hair, bright smile

The color contrast between the teal and the pink wall was a nice bonus.

Lissa tugging jumper strap confidently Lissa with arms crossed, mischievous side-eye Lissa laughing candidly

Confident, mischievous, then a real laugh. That’s range.

Look Three

The One You Don’t Want to Cross

All black — leather jacket, mock neck, key pendant necklace, newsboy cap. This was Lissa’s dramatic range: the villain, the femme fatale, the one with a secret. New playlist, new energy, and she locked right into it.

Lissa in black leather jacket, intense look over shoulder Lissa leaning on iron gate, smoldering look

The leather jacket plus that iron gate. It just works.

Lissa in newsboy cap, arms crossed, serious Lissa with arms up on iron gate, direct dramatic gaze Lissa in cap and leather jacket, mysterious street portrait

Cap on, attitude dialed up. Three totally different reads from one outfit.

The whole session took about 45 minutes — three looks, three characters, quick changes in the car, and a team that worked well together. Lissa came in with a plan, and it shows. These aren’t just pretty pictures; they’re tools. Each one is designed to tell a casting director something specific about what she can do before she even walks in the room.

Graduation’s coming up. After that, the auditions start for real. She’s ready.

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