Wauwatosa West class of 2027 Sneak Peek | Will

What do you wear when you only get one outfit? No bag of backups in the car.

I’ve watched seniors stress over that single choice harder than a final exam.

Will didn’t stress. Will wore a suit.

He leaned into that wall, hands folded, like he had a board meeting at noon and somewhere more important to be at two. Seventeen years old. Completely unbothered.

And THAT is how you do an Express Session.

Congratulations to Will from Tosa West on your upcominig graduation with the class of 2027.

Wauwatosa West senior boy in a gray suit and navy tie leaning against a stone wall on a wooden bridge for his senior portraits near Milwaukee, Wisconsin

Here’s my wardrobe talk, short version: when it’s only one outfit, what you choose really matters. So keep it simple...and make it count.

Simple doesn’t mean safe.

Safe is the hoodie you wore last Tuesday.

Simple is one strong choice: a suit, a sharp jacket, the dress you’ve been saving for something. Not the dressy type? That’s ok. Make your wardrobe choice fit your personal style - maybe it’s a sweater you really love or a polo that brings out the blue in your eyes.

Will picked the suit because that was what HE wanted to wear.

Now the part for the parents…

An Express Session is the simple option, not the lesser one.

One outfit, one location, and your senior still walks away with portraits worth framing. It’s built for the kid juggling three sports and a job, the one who gave you a flat “fine” (or even a “no”) when you brought up senior portraits. This is the session you book when you’re simply short on time.


I photograph high school seniors from Wauwatosa West, Wauwatosa East, Brookfield, Elm Grove, New Berlin, Pewaukee and all over Milwaukee and Waukesha County, from my studio at 155 S. Executive Dr. in Brookfield to a park near you.


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Wauwatosa East class of 2027 Sneak Peek | Oliver