Leila Bailey-Stewart Photography

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Leila Bailey-Stewart Photography

Lifestyle and Portrait Photography

10/27/2026

A Different Kind of Bloom. 🌻

Strength doesn’t always have to be loud.

Sometimes it’s found in the contrast. In the unexpected. In the space between softness and power.

A little fashion. A little nature. And a whole lot of presence.

Not your average garden-variety editorial.

What caught your eye first? The fashion, the flowers, or the feeling?

Model: Brandon Hogan
Hair & MUA: Jenn Jackson l Hair • Makeup • Male Grooming • Education
Fashion Stylist: Kadon Brown
📍 Chicago | Bokeh Photo Summit
📷 Captured with Canon USA R5 MII & RF 24-105 f4
🔦 Westcott Lighting FJ250

10/25/2026

Join me there. Get your ticket today. You don’t want to miss this!

10/23/2026

Fashion without permission. ⚡️

Who says the runway needs four walls?

A little neon. A little attitude. And a whole lot of confidence.

Chicago gave us the architecture. We brought the editorial energy.

Another frame of creativity from Lakil.

Model: thereal_lakil
Hair: Alicia Igess | Bridal & Special Events Hairstylist
MUA: ATLANTA HAIR & MAKEUP | Jaylei 💄
Fashion Stylist: Kadon Brown
📍 Chicago | Bokeh Photo Summit
📷 Captured with Canon USA R5MII & RF 24-105 f4
🔦 Westcott Lighting FJ250

10/20/2026

Presence isn’t something you put on. It’s something you bring.

No introduction needed.

A little mystery. A lot of intention. And the kind of confidence that speaks before you ever say a word.

Chicago after dark. Where fashion meets attitude, and every frame tells its own story.

Model: Brandon Hogan
Hair & MUA: Jenn Jackson l Hair • Makeup • Male Grooming • Education
Fashion Stylist: Kadon Brown
📍 Chicago | Bokeh Photo Summit
📷 Captured with Canon USA R6 MIII & RF 50 1.2
🔦 Westcott Lighting FJ400 (Modeling Lamp)
🐆 CheetahStand C10

Which frame commands your attention?

10/16/2026

Elegance doesn’t have to be quiet.

A little drama. A little edge. And a whole lot of presence.

The gold. The textures. The attitude. Every detail had something to say.

Chicago gave us the backdrop. Lakil brought the energy. 🔥

Fashion is the expression. Confidence is the statement.

Model: thereal_lakil
Hair: Alicia Igess | Bridal & Special Events Hairstylist
MUA: ATLANTA HAIR & MAKEUP | Jaylei 💄
Fashion Stylist: Kadon Brown
📍 Chicago | Bokeh Photo Summit
📷 Captured with Canon USA R5MII & RF 24-105 f4
🔦 Westcott Lighting FJ400
🐆 CheetahStand C10

Which frame is your favorite — 1, 2, or 3?

09/27/2026

I’m so excited to join the Shutterfest stage. Meet me there and get your tickets now! Drop 💜 if connection and confidence is important to you!

09/13/2026

SAME LOOK. DIFFERENT LIGHT.

One direct. Graphic. Unapologetic.

The other softer. Quieter. More cinematic.

Same woman. Same styling. Two completely different ways of seeing her.

That’s what I love about light. It doesn’t just illuminate the story. It can change the way the story feels.

Created at Bokeh Photo Summit.

Model Jamila
Hair Alicia Igess | Bridal & Special Events Hairstylist
Makeup Olivia K.✮ (STL MUA✈️)
Styling Kadon Brown
Event Bokeh Photo Summit
Model coordinator All Things Booked & Busy

📷 Canon USA R6 Mark III + 85mm

Boston-based and available for beauty, portrait + editorial commissions. Travel inquiries welcome.

09/09/2026

MORE IS A DESIGN CHOICE.

The coat. The stripes. The shape. The attitude.

Nothing here is asking to be subtle.

And that’s exactly the point.

Model: Lex🌻
Style: Kadon Brown
Hair: ATLANTA HAIR & MAKEUP | Jaylei 💄
Makeup: Atlanta Luxury Hair & Makeup | Christine Amelie
Source: All Things Booked & Busy
Event: Bokeh Photo Summit

📷 Canon USA R6 Miii+ 85

09/06/2026

STRIPPED BACK.

No elaborate set. No color story doing the heavy lifting.

Just denim, light, form and presence.

I love a portrait that knows when enough is enough. Sometimes taking things away is exactly what lets the person come forward.

Model: Ty Williams
Source: All Things Booked & Busy

Created at Bokeh Photo Summit.
CheetahStand Nanlite USA

📷 Canon USA EOS R5 Mark II + RF24-105mm F4 L IS USM

Men’s portraits don’t have to feel corporate.

Ready for something with a little more presence? Now booking portrait + editorial sessions in Boston and beyond. Link in bio.

05/11/2026

Out with the old… snap into the new 😮‍💨

Been rocking the OG for years, but this upgrade? Yeahhhh… they did what needed to be done. The fit, the feel, the snap-in action… smooth every time.

Little things that make moving through shoots faster, cleaner, and way more fun.

Appreciate gear that actually keeps up with the chaos. 🕷️📸

Address

Boston, MA

Website

http://leilabaileystewartphotography.com/

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