Skyline Headshots
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Skyline Headshots
I'm your headshot specialist in Chicago. My job is to equip you with images that you're proud of - and give you the confidence to go put those images to work. During your shoot, it's my job to be your expression coach, your hype man, your supplier of ridiculous jokes. I want to transform how the world sees you, and how you see yourself.

Others will see and judge the portraits you use to showcase your personal brand, long before they hear what you have to say. Your headshot is just the start. Skyline Headshots offers custom portraits and branding to let the images speak for you. You've probably seen that there are a TON of background options.
Reviews (11)
Lindsay Sherman
Lindsay Sherman
Jan 12, 2022
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Positive: Professionalism, Quality, Responsiveness
I am literally the least photogenic human on the planet and I left with beautiful headshots. Garrett is a camera magician. 10/10 would recommend!!
Mmcferrin
Mmcferrin
Dec 17, 2021
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I was very happy the pictures that Garrett took. He created a very comfortable environment and made me feel at ease, which translated to a shot that I was very pleased with. I would highly recommend Garrett and Skyline! 5 STARS!
Megan Cameron
Megan Cameron
Nov 15, 2021
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Positive: Professionalism, Quality, Responsiveness, Value
Garret was a joy to work with! He worked hard with me to find my best angles, and made sure that I'd have several shots I loved to take home. His editing works magic, while leaving you looking like your most natural self!
Ryan Lavelle
Ryan Lavelle
Oct 26, 2021
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Positive: Professionalism, Quality, Responsiveness, Value
What a fun experience with Garrett and Skyline Headshots! He's kind, professional, funny, and great at what he does! Made the whole experience of being in front of a camera comfortable and enjoyable. 10/10 headshots! Would love to use him more in the future!
Sergio Mendez Roa
Sergio Mendez Roa
Oct 26, 2021
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Positive: Professionalism, Quality, Responsiveness, Value
Garret is a complete professional. He certainly is a perfectionist, as he is always looking for the most perfect shot. His kindness and creativity takes you on a journey to explore the boundless possibilities photography has to offer. Having been let down by two photographers last year, I am glad to have found Garret.
Jose Jimenez
Jose Jimenez
Aug 30, 2021
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I want give a huge shout out to Garret Buckley at Skyline Headshots for a wonderful experience. Having never gotten a headshot I didn’t know what to expect. Garret is both professional and personable. I came into his studio nervous and apprehensive, but left feeling confident and empowered by his work! I highly recommend his services.
Hailey Kurtz
Hailey Kurtz
May 19, 2021
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Garret is a delightful individual to work with and a very skilled photographer. He did an excellent job on our company's professional headshots. We reached out to him in a crunch and he was super accommodating to fit 10 people in in no time. They all made comment on how friendly he was too! His turn around time was very speedy and his responsiveness was unmatched. We had a wonderful experience with Skyline Headshots and will without a doubt be returning for future photos.
Austin Miller
Austin Miller
Oct 23, 2020
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Recently, I needed an updated headshot. After seeing Garret’s work, I decided to visit his studio. Right from the start, he made me feel welcome and comfortable. Normally I don’t like getting my picture taken,… but I was at ease and was able to relax. This photographer knew what he was doing, directed me the whole time, and continually reassured me. In the end, I was stunned to see the images! Without question, he produced the best headshots I have ever had taken of me! I would recommend this studio to anyone; it’s worth every penny!
Caroline Smith
Caroline Smith
Jul 30, 2020
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Great headshots! The experience was easy and comfortable. I’d recommend garret for any pictures you need!
Hannah Schmuck
Hannah Schmuck
Jul 19, 2020
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Garret was very professional but personable so I felt comfortable during the shoot. Studio was clean and set up really well - the headshots turned out perfectly and I am very impressed!
Sharon Solomon
Sharon Solomon
Dec 30, 2019
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We had Buckle Down Media cover our engagement ceremony in Naples, FL. Garret was extremely friendly and creative with his shots. He came early to scout out the venue and was prepared with photo ideas which made… the process much easier. Josh and I both thoroughly enjoyed working with him. He even came in very handy when we needed extra batteries for the event and offered to help!! He was very accommodating throughout the event. We would recommend Buckle Down Media photography services to anyone seeking a friendly yet profession experience!