A well-dressed Milwaukee Senior Session
Dartanion poses with a bowling ball at sunset in Milwaukee.

A well-dressed Milwaukee Senior Session

I’m excited to share with you the results of one of the most exciting and creative photo sessions that I’ve ever done.

Dartanion graduated in 2021 from Wauwatosa East High School. I got connected with him after a friend’s mom contacted me about doing a combined senior session with Dartanion and Emory. (Don’t worry, I’ll post Emory’s photos soon as well).

Group sessions

This was one of two combined sessions that I did that season, which raises a great point I want to make with you, if you’re considering signing up for your senior session with me.

If you’d want to make the experience a little bit more affordable consider signing up with a friend and getting a group rate.

Dartanion and Emory wanted to take photos in multiple locations, and for multiple hours. Since, I wasn’t going to be adding more time and locations than if it was just one student I said that we could do it all for an additional 33% of the package.

Although, it was more than my normal rate, it allowed both mothers to overall pay less than they would have if they had gone by themselves.

It’s a great option if you have a senior that’s not too excited about the photos. First off, their friends will help them loosen up during the session and you can pay less if you know your senior doesn’t care to have that much variety.

My other group high school senior session was with three boys and none of them were excited about the pictures, so I did the whole thing in 90 minutes with each boy getting about 30 minutes of photography time. 

It gave them about 20 photo options afterwards and because there were three of them they could split the cost and pay a lot less than if it was just one student. The more friends you can sign up, the lower your individual cost will be!

Edgy and industrial locations in the city

I first started Dartanion’s portrait session outside Fiserv Forum in downtown Milwaukee and I could tell right away that Dartanion was a high schooler that would be going places in the future. He was confident in the way he talked and was good at relating to adults.

He also had a clever and fun personality. While, I was taking photos of Emory, Dartanion had snuck off to buy some cookies at Insomnia’s Cookies.

I didn’t know what had happened and then I turned around and he was happily munching on them, saying they were his favorite cookies. 

Hey, sometimes photo sessions can run long and if it makes clients happier to be eating a snack in the downtime than that works great for me. In fact, I’ll now officially suggest that as a method to make the sessions go better.

Dartanion started the session off in his bright red Wauwatosa East High School Red Raiders sweater and switched back and forth between that and a black Nike hoodie.

Him and his mom also showed me off his personality, because Dartanion is a great bowler and he had brought some of his bowling gear along.

I didn’t ask him to get this out right away, because I knew I wanted to use it later in the session. I had a couple ideas for big dramatic shots that were more possible at the second and third location. 

After Fiserv, our second location was Commerce Street by Lakefront Brewery and the Milwaukee River. Here there is a great big long walkway that comes out of a hillside forming a bridge. 

It’s a great place to silhouette students against the sky and as it got darker I was able to get a great picture of Dartanion pulling the ball back like he was going to bowl a strike. He was facing me and I was able to isolate him high against the sky.

Of course, my favorite photos of him bowling I took even later at night in front of Lakeshore Park with the US Bank building in the background. I love this spot and we had waited all the way until it was night time.

At this point, the lights from the US Bank building were on and shining behind him and I used my telephoto lens to make the building look up close and personal. I also took my flashes and added a bit of bright red gel and used it to add a bit of a fun vibrant color on one side of Dartanion’s face, giving the scene maybe a “glow under the neon lights” kind of vibe.

If you want to see more examples in this same locations, check out Ethan’s post or to see more creative portraits check out Hannah’s pictures.

Dartanion’s example on how to dress well

The other thing I wanted to highlight for Dartanion was that he nailed the fashion portion of the senior session.

Knowing what to wear can be a little bit daunting for everyone. After all, we all want to look good and don’t want to make a fool of ourselves. But, we also want some clothes that make us feel comfortable and confident and show our true selves.

What I always suggest to clients is to wear an upper-casual outfit, like when you go out to eat at night with friends, wear a dressier outfit, like where you’re going to a wedding, church or any formal occasion. Finally, bring a third outfit that shows off your personality: like sports gear, or vintage thrift, or that flowing dress with a wide brim hat.

Dartanion nailed all of these suggestions. His outfit at the beginning was casual, but also showed off his interests with the Wauwatosa East High School representation. Then for the second location Dartanion changed into a full two-piece suit and tie and tie bar.

He looked amazing in it and I love it so much when seniors wear suits. It’s such a show stopper. In case you’re wondering: yes it’s not common, but it’s happened to me three separate times, so it’s also not unheard of.

It immediately raises the level of the portraits and showcases the unique moment for what it is: a special time that celebrates you graduating from high school.

It also helped that Dartanion knew how to pick a suit. It was well-fitted and he chose a navy blue suit and red tie.

For his last outfit, Dartanion again showed off his personality and interests by switching into his bowling outfit, complete with his bowling glove and ball. After the session, Dartanion’s mother got a hold of me and even asked about sending a photo to Motiv, the maker of the bowling ball and obviously one of Dartanion’s favorite brands.

I don’t know if it helped, but hopefully they sent him a new bowling ball!

If you’re ready to brainstorm how to use your hobby or sport in a photo session, please send me an email at matt@bigskyphoto.com and we’ll have you looking as epic as Dartanion in no-time.

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