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Downtown Winter Garden Senior Pictures: Josh’s Editorial-Inspired Shoot

Josh was one of my senior reps, and after photographing his actual senior session at Mead Botanical Garden, we decided to do one more shoot together just for fun. For this one, we headed to Downtown Winter Garden and planned something completely different with more of a fashion-inspired, editorial feel.

Since this wasn’t his actual senior session, we had a little more freedom to experiment and just create. Josh is always fun to photograph because he’s easygoing and pretty much up for anything I suggest, which made him perfect for this idea.

Thankfully, that also included being willing to wear a jean jacket in Florida in May, because it was HOT.

Senior guy in a denim jacket during an editorial shoot in Downtown Winter Garden

An Editorial-Inspired Shoot in Downtown Winter Garden

Josh wore one outfit for the entire shoot: jean shorts, a matching jean jacket and a white shirt underneath.

Even with just one outfit, we were able to create a lot of variety by changing the surroundings, lighting and overall feel as we moved through Downtown Winter Garden.

We started around the old train station and then walked through different parts of downtown, stopping anywhere that caught my eye. We used the mural, some of the side streets, the steps of the parking garage and eventually made our way to the top of the garage.

One general area gave us completely different looks without needing to spend our time driving from place to place.

Senior guy posing near the historic train station in Downtown Winter Garden
Senior guy posing in front of a colorful Downtown Winter Garden mural

That’s one of the things I love about photographing senior pictures in Downtown Winter Garden. You can walk a relatively small area and find brick, color, streets, architecture, rooftops and tucked-away spots that photograph completely differently from one another.

If you want to see another way I’ve used the area, take a look at Sebastian’s Winter Garden senior pictures session, where we combined Downtown Winter Garden with Oakland Nature Preserve for two very different settings.

Senior Pictures for Guys Don’t Have to Feel Basic

I think there’s sometimes an assumption that senior pictures for guys need to be pretty simple — find a good location, put him somewhere and take the picture.

They absolutely can be simple if that’s what your senior wants, but they don’t have to be.

With Josh, we were creating something with a little more edge. His serious expressions worked really well with the denim outfit and downtown backgrounds, and he was completely willing to lean into the fashion/editorial direction we were going for.

We also pulled out my off-camera lighting for some of the photographs, which changed the look even more. Those ended up being some of the images Josh got especially excited about. I remember showing him the back of my camera after we took them, and he absolutely loved what he saw.

I love moments like that, when we try something different and the senior immediately gets excited about what we’re creating.

Editorial senior portrait created with off-camera lighting
Fashion-inspired senior picture in Downtown Winter Garden

If you have a senior guy who wants something beyond the standard senior portrait, tell me. We can plan around his style instead of trying to make his session look like everyone else’s.

[INTERNAL LINK — Senior Pictures for Guys | Orlando Senior Photos]

Apparently We Also Needed Senior Assassin Security

There was one other thing happening during this shoot that had absolutely nothing to do with photography: Senior Assassin.

If you have a high school senior right now, there’s a pretty good chance you know exactly what I’m talking about.

The game was in full swing when we photographed Josh, so his mom and dad followed us around Downtown Winter Garden and spent basically the entire shoot keeping an eye out.

I was watching for photographs while they were watching for assassins. 😂

Nothing like trying to create serious editorial senior portraits while your parents are simultaneously running security.

Senior guy walking through Downtown Winter Garden during an urban photo shoot

It was also unbelievably hot that day, and Josh was such a sport about it, especially considering the jean jacket. At one point we finally stopped at Foxtail so we could cool off, grab something to drink and take a little break before heading back out to finish the shoot.

Downtown Winter Garden Gives Us So Much Variety

After photographing around the train station, mural and side streets, we worked our way over to the parking garage.

We used the steps first and then headed all the way to the top, where we were able to create a completely different look from the older buildings and streets below. The rooftop worked especially well with Josh’s denim outfit and the stronger expressions we were using throughout the shoot, and it fit perfectly with the editorial direction we had planned.

Senior guy posing on the Downtown Winter Garden parking garage steps
Rooftop senior portrait in Downtown Winter Garden

We also brought out his cap and gown while we were downtown and added some graduation photographs into the mix.

That’s another easy way to create more variety without completely changing what we’re doing. The location stays the same, but adding the cap and gown immediately gives us photographs that feel completely different from the rest of the shoot.

Senior wearing a cap and gown in Downtown Winter Garden

How Shoots Like This Became The Creative Series

Looking back now, shoots like this one with Josh were part of what eventually turned into what I now call The Creative Series.

One of the things I loved about having a senior rep program was having a reason to create extra shoots that weren’t tied to someone’s actual senior session. It gave us room to try an idea simply because it sounded fun and see where we could take it.

That’s exactly what this Downtown Winter Garden shoot was.

Josh and I decided we wanted to do a fashion-inspired editorial shoot, picked Downtown Winter Garden as our location and went out and created it. Since we had already done his senior session, this shoot could have a much more specific look and feel, and I could experiment with things like stronger expressions and off-camera lighting.

Eventually, I realized I didn’t need a rep team to keep the part of it that I loved most.

That’s where The Creative Series came from.

Now, my booked seniors can have opportunities throughout their senior year to participate in additional themed, editorial and creative shoots outside of their regular senior session. It gives us a chance to try ideas that might be completely different from anything we planned for their main senior pictures.

When I look back at sessions like this one with Josh, I can definitely see the beginnings of something that has now become a really fun part of the senior experience I offer.

[INTERNAL LINK — Addie’s 50s-inspired session/The Creative Series post once published]

Creative editorial senior portrait featuring a denim outfit

Planning Senior Pictures That Fit Your Guy

Of course, your senior guy doesn’t need a jean jacket, off-camera flash and a rooftop to have great senior pictures.

Some guys want natural, relaxed photographs. Some want sports incorporated. Others may want music, cars or another interest included, and some are totally up for creating something more fashion-inspired like we did with Josh.

That’s why I like figuring out the direction before the session instead of showing up with the exact same plan for everyone.

If your senior already has ideas, I want to hear them. And if his answer to every question about senior pictures is basically, “I don’t know,” that’s okay too. We can figure it out together.

[INTERNAL LINK — Orlando Senior Photography Experience]

Downtown Winter Garden senior portrait featuring a denim outfit

Downtown Winter Garden Senior Pictures: Frequently Asked Questions

Is Downtown Winter Garden a good location for senior pictures?

Yes! Downtown Winter Garden gives us a lot of visual variety within a fairly small area. We can use historic architecture, murals, side streets, brick, parking-garage areas and other downtown backgrounds without spending the session driving from location to location.

Are Downtown Winter Garden senior pictures good for guys?

Definitely. The downtown backgrounds work especially well if your senior wants photographs that feel a little more modern, casual or fashion-inspired. We can also change the look quite a bit depending on his outfit, the areas we use and the style of lighting.

Does a senior guy need several outfits?

Not necessarily. Josh wore one denim outfit for this entire shoot, and we created variety by changing locations and lighting and adding his cap and gown. For an actual senior session, we can talk through outfits during planning and decide what makes the most sense for the photographs your senior wants.

Can we create more editorial senior pictures?

Absolutely. If your senior likes fashion-inspired photographs, stronger expressions, creative lighting or something that feels different from traditional senior portraits, tell me during planning. We can use those ideas to help shape the session.

What is The Creative Series?

The Creative Series gives my booked senior clients opportunities to participate in additional creative shoots throughout their senior year. The concepts can be themed, editorial, seasonal or simply something fun we want to try, and they’re separate from the senior’s regular session.

Can we include cap and gown pictures?

Yes. Cap and gown photographs can be worked into your senior experience, and we can plan them so they fit naturally with the rest of the photographs we’re creating.

Ready to Plan Senior Pictures That Feel Like Your Senior?

This shoot with Josh started because we thought it would be fun to create something with more of an editorial, fashion-inspired feel. We had a great denim outfit, Downtown Winter Garden, some creative lighting and a senior who was completely willing to go along with whatever I threw at him — even in a jean jacket in May, with his parents on Senior Assassin patrol.

Looking back, I can also see how shoots like this helped shape the creative opportunities I now offer my booked seniors through The Creative Series.

And when it comes to your senior’s actual session, we’ll plan that around him. If he already knows exactly what he wants, great. If he has no clue at all, that’s completely fine too. We’ll talk through his style, locations, clothing and ideas and figure out what makes sense for him.

[INTERNAL LINK — Contact Melissa]

Editorial rooftop senior portrait in Downtown Winter Garden