IML Portraits2026-05-18T21:29:38+00:00

Leather Photo Sessions at IML

Leather photo Sessions at IML

Convenient, cinematic portrait sessions in Chicago during International Mr. Leather weekend — ready for leathermen, kinksters, titleholders, first-timers, and anyone who wants to be photographed in their gear.

All sessions include high resolution digital images and a selection of artistic edits from the session.

Choose your session

Portfolio Mini-sessions

Free | 15 minutes

Quick, polished portraits in curated Chicago locations during IML weekend.

These images will be used on social media and for marketing purposes by J-Bo Gray Photography.

Includes digital images from the shoot + 3 artistic edits.

Signature Session

$199 | 50 minutes

More time, more direction, and more flexibility for a wider variety of final images.

These images will not be required for social media and for marketing use by J-Bo Gray Photography.

Includes digital images from the shoot + 10 artistic edits.

Free 15 Minute Mini-Sessions

Urban Park

A softer outdoor look with greenery, open air, city texture. Great for portraits that feel clean and natural accompanied by the Chicago cityscape in the distance.

  • Friday — 10:00 AM / 10:30 AM / 11:30 AM

Urban Tracks

An edgier city backdrop beneath the Chicago “L” (aka CTA) tracks, with alleyway texture, steel, and a more cinematic urban feel.

  • Friday — 11:00 AM

  • Saturday — 10:00 AM / 10:30 AM

  • Sunday — 10:00 AM / 10:30 AM / 11:00 AM / 11:30 AM

Urban Alleyway

A gritty, industrial portrait setting with alleyway walls, loading dock texture, and a stronger editorial feel.

  • Friday — 3:00 PM / 3:30 PM /4:00 PM / 4:30 PM

  • Saturday — 3:00 PM / 3:30 PM / 4:00 PM / 4:30 PM

  • Sunday — 5:00 PM / 5:30 PM

Want More Time? Book a Signature Session – $199

Urban Lakeside

A bold waterfront setup with Lake Michigan, open sky, and the Chicago skyline behind you. Great for cinematic portraits, especially when photographed in the evening. (Requires a short uber ride to location)

  • Friday — 7:00 PM (50 mins)

To Be Determined

Do you have a location request or special idea you have in mind? Get in touch with me on Instagram (@jbogray) or via email at jbograyphoto@gmail.com to discuss your idea, or book and trust me to surprise you with a great setting for your portraits.

  • Friday Morning — 8:30 AM (50 mins)

  • Saturday Morning — 8:30 AM (50 mins)

What to Expect?

You do not need to be a model.

I’ll direct you through posing, expression, and how to use the space.

Bring your favorite Gear!

Leather, rubber, denim, boots, harnesses, uniforms, pup gear, title sashes, or whatever makes you feel most like yourself.

These shoots move quickly!

Please arrive 10-15 minutes early to your scheduled time. Since these are short sessions, late arrivals will impact what we can shoot.

Turnaround time will be a few weeks.

I anticipate booking 30+ shoots across IML weekend. That’s a lot of editing! Current estimated time is 4 weeks, but it’s worth it!

Got Questions? Check out these FAQs!

Are the mini shoots really free? What’s the catch?2026-05-12T06:13:50+00:00

Yes! I am offering the mini-sessions absolutely free of cost! Why? I have been an international award-winning photographer for the past 15 years, but I haven’t branched into leather and gear portraits until this year. I keep my vanilla business separate from my leather, so I’m building a portfolio from scratch. That’s where I need help. These sessions are specifically for me to be able to build my portfolio which is why a model release will be required for all shoots. Signing a model release is optional for signature sessions.

What is the difference between a free mini shoot and a paid shoot?2026-05-12T06:13:50+00:00

Mini-sessions are rapid paced, location-specific 15-minute sessions. Just long enough to get some solid portraits.

Signature Sessions are 50 minutes, which gives us more time, more flexibility, and more image variety. More equipment is involved and this allows us to get more technical with the location, posing, and lighting. This session is long enough to create solid artwork and an experience you won’t forget!

Do I need expensive gear or a full leather look?2026-05-15T06:39:49+00:00

No. You do not need to have a full leather wardrobe or titleholder-level gear. However these are specifically leather and gear shoots, so some level of gear is required for my free shoots. If you don’t have much gear, please still book, but IMMEDIATELY contact me on instagram (@jbogray) or email me at jbograyphoto@gmail.com. Please let me know what you do have and what your sizes are. I will do my best to acquire some loner gear in your size for the shoot.

Can I book more than one session?2026-05-12T06:13:50+00:00

No. At least to start.

If additional spots are open closer to the event, I may reach out to let people book multiple sessions, but I do anticipate a fully booked schedule for the weekend.

Where exactly are the sessions?2026-05-12T06:13:50+00:00

Exact location details will be sent within a couple days of your session and the morning of your session. The location names describe the general visual style of each session.

Please plan for around a 10 minute walk from the IML host hotel. For the Urban Lakeside sessions, please plan for a 10-15 minute Uber ride (and additional time for the uber to arrive!)

What if the weather is bad?2026-05-12T06:13:50+00:00

As everything will be photographed outdoors, sessions may shift, adjust, or be rescheduled depending on weather and safety. I will be in contact if that is the case.

Can I bring a friend or partner?2026-05-12T06:13:50+00:00

Yes, but please keep in mind that mini shoots are very short. If you want photos with another person, book one time slot together rather than trying to split separate sessions.

What should I wear?2026-05-12T07:19:06+00:00

Wear whatever makes you feel most like yourself: leather, rubber, boots, harnesses, uniforms, pup gear, title sashes, or other gear that photographs well! The most important thing is that you feel confident and comfortable moving in it.

If you have something very unique or hard to find, feel free to bring that!

If you want any guidance, my opinion on what will shoot best, or to share what unique gear you have that you want photographed, please feel free to contact me on instagram (@jbogray) or email me at jbograyphoto@gmail.com.

How many images will I receive?2026-05-12T06:13:50+00:00

Mini-sessions will include a small final gallery of around 20-25 images with 3 artistic edits.

Signature sessions will include a larger final gallery because we’ll have more time to create variety. Expect around 40-50 images with 10 artistic edits.

Will my photos be posted publicly?2026-05-12T06:13:50+00:00

If you are booking a mini-session, yes. Usage/credit expectations will be confirmed before images are shared publicly, but these images are specifically meant for portfolio and display purposes. Your face or certain body parts do not need be shown, however please bring hoods or other gear that conceals your identity if you would prefer it not to be shown publicly.

If you are booking a signature session, you may opt out of this.

Ready to Be Photographed at IML?

Choose the location that fits you best, grab a time, and show up in your favorite gear ready to be photographed.

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