Headshot of the Month is a free, public contest open to anyone who wants to showcase their best headshot to our community. Entries are critiqued live by Peter Hurley and Headshot Crew mentors during a public Crew Cast, offering valuable real-time feedback.
Peter looks for images that demonstrate the strong fundamentals taught in the coaching program—natural expression, clean lighting, and a genuine connection with the subject. After the review, he selects a grand prize winner, and a second prize is awarded to one random participant.
With prizes from monthly sponsors, HOTM is a fantastic way to challenge yourself, get expert insight, and experience the Headshot Crew coaching program in action.
If you’re not yet a member of the Coaching Group, we offer a free introductory course where you can get a feel for what Peter is looking for and the standards we uphold at Headshot Crew.
September Headshot of the Month, sponsored by Westcott
Westcott is sponsoring the September Headshot of the Month with two prizes.
First place: Westcott V-Flat 2-Pack, $489 value
Two full-size portable V-flats, one black fabric and one white. Each opens to 82 by 84 inches and folds anywhere from 15 to 180 degrees. Bounce soft fill with the white side, add negative fill with the black, flag a window, or stand one up as a background. Aluminum frames, no tools, and Westcott says one person is set up in under five minutes. The fabric is machine washable and does not warp, dent, or fade. It all packs into a 45 inch case that fits in a back seat, so these go on location with you.
Randomizer: Westcott Photography Wagon, $189 value
A collapsible rolling gear cart that hauls up to 175 pounds of lights, stands, and cases in one trip. The included boom pole mounts to the wagon and turns it into a mobile light stand, holding 13 pounds of gear up to 7 feet 8 inches high. Locking swivel wheels keep it planted. Three steps fold it down to 29 by 19 by 8.5 inches, and it weighs 24 pounds.
The randomizer prize is drawn at random from every entry. Enter your headshot and you are in the drawing. You must be present on the Crew Cast to win.
Contest Rules
- Upload your best headshot.
- Images must be uploaded before the deadline above.
- Headshots only.
- No Selfies
- Color images only.
- One entry per person
- You can't re-enter the same shot if it's already been entered in a previous HOTM competition.
- Winners will be chosen by Peter Hurley LIVE on a Crew Cast after the contest deadline.
- Click on the thumbnails below to view the larger image, leave comments, and rate your favorites.
- You can only win HOTM once, but you can still enter to get feedback even if you have won in the past .
The Grand Prize Winner will receive
- A 2 pack Westcott V-flat set
- One free year's membership to the Headshot Crew coaching groups (up to $500)
- Peter's Fstoppers Tutorial set
- A PhD (Peter Hurley Doctorate) badge on your profile.
One Random Winner will receive
- A Westcott Photography Wagon
This is a Public contest. Anyone may enter.
Thu, 10/01/2026 - 3:12pm EDT
Create a Free Account or log in to enter this contest.