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Engaging Moments: Expert Advice on a Picture-Perfect Engagement Session

If a picture is worth a thousand words, it’s no surprise we all want that picture to be unforgettable. And with the intense focus of a wedding, you can bet brides and grooms are looking for downright perfection. While wedding-day photography captures the essence of one of the most important days of a couple’s lives, engagement photography sets the tone for your road to wedded bliss—and the beginning of an important journey with your photographer.

“Many of our clients have become some of our closest friends; that reflects the investment we put into each one of our couples who allow us to capture their wedding and future milestones,” says Sarah Spottswood, co-owner with husband Steven of Spottswood Photography in Milwaukee. “This is always our reminder of why we document these special moments for people.”

Much like wedding photography, each engagement session is unique. From the location to the wardrobe, theme and poses, engagement photos are a personal reflection of each couple. Here, some of Wisconsin’s top wedding photographers share their advice for achieving your dream engagement photos.

Preparing for Perfection

While every photographer has their own unique process for capturing engagement photos, they all have one thing in common: They need to get to know you as a couple, and what makes you tick. From a consulting conversation to meeting at your favorite restaurant or even visiting your home, a photographer should do everything they can to make you comfortable with their process.

“We tend to ask our clients some personal questions, like where they met or their favorite dinner spot or bar, and potentially shoot in that environment,” says Matt Haas, owner of Matt Haas Photography in Milwaukee. “We even urge our clients to let us in their homes to start a session.”

According to Spottswood, the engagement session is really a “getting to know our couples” session. It helps build rapport and trust between the photographer and the couple—and in the end, ensures the best possible wedding photos. “Engagement sessions really create a connection with our couples. Couples are more vested in their photography, and the images showcase that.”

But let’s be honest: No matter how much you prepare, that first photo session with your photographer can be awkward—at least in the beginning. “We tend to feel uncomfortable in front of the camera and don’t know what to do with our hands. It’s entirely normal,” says Fort Atkinson-based photographer Jenna Kutcher. The goal is to interact with each other and forget that the photographer is even there; as time goes on, she says, it gets comfortable and fun.

“I want you two to flirt and be in love and laugh and talk about ice cream (or glitter or unicorns or anything that makes you laugh!),” adds Kutcher. “I promise I won’t put you into a million awkward poses or make you try to duplicate weird photos I’ve seen before; this is all about you and how you are most comfortable.”

A Winning Wardrobe

It can be a daunting task to achieve a look that is both timeless and on-trend. But when it comes to engagement photography, the fashion advice from our photographers is pretty simple: Choose outfits that reflect your personal style and complement one another, without going the way of the 1980s family portrait. Translation: Avoid matchy-matchy.

“I want these images to scream ‘you’ in your most genuine form, so wear things that you would wear in real life,” says Kutcher. “Don’t worry about matching or bold colors—color is good, and a little eclectic taste never hurt anyone. I love classic looks that you won’t laugh at 30 years from now when your children poke fun at today’s fashion trends.”

“These photos will reflect one of the best times of your life, so bring something that will represent that,” says Spottswood. “And remember to pick outfits that best fit your location.”

When in doubt, don’t be afraid to dress up. “Even if you are a casual couple, do a casual look, but then also a dressier look,” says Lottie Royten, owner of Lottie Lillian Photography in Milwaukee. “After all, you will be dressed up on your wedding day, so why not start now?”

Trends Worth Trying

As with weddings, engagement photography trends are plentiful, but should be approached with careful consideration. Just because it looks good on Pinterest doesn’t always mean it will translate when it’s you and your beloved in front of the camera. With this in mind, our photography experts say personalization is the best trend.

“Honestly, when I think about trends, it’s anything goes,” says Royten. Photos that reflect a couple’s vibe are the hottest trend of the season, whether that’s playing sports or games, getting outdoors, or heading to your favorite bar or restaurant.

“It’s all about images that represent the couples’ personalities—whether that’s documenting them doing something they love together or just relaxed, natural images of them, madly in love,” says Kutcher. “Often, selecting a season or location opposite of the vibe of the wedding is fun for variety. Snow, for example. We do live in Wisconsin—and should take advantage of that.”

One of the best ways to capture the essence of a couple, say our experts, is to spend time with them in a setting that feels natural and, above all, comfortable. That’s the key to truly embracing the personalization trend.

“We love ‘date spots,’ and encourage our couples to choose a date to take us on,” says Spottswood. “Wineries, breweries, rollerblading along the lakefront, hiking trails—choosing a location or activity that the couple loves or that holds a place in their hearts also helps to achieve that photojournalistic look that is so timeless yet on-trend for 2017.”

From mastering photo prep to creating picture-perfect outfits and setting the scene, the art of engagement photography that is uniquely you is as easy as following a few simple tips and remembering to always be yourself.

“I love engagement sessions for so many reasons, but most of all, I love giving couples photos of their real life—the kind that you look at and smile and connect with years down the road,” says Kutcher. “I promise, it will probably be the easiest thing you do while wedding planning.” *

Kate + Adam

Choosing a photographer was a no brainer for Kate Shelerud and Adam Eskuri—Kate’s sister is reknowned shutterbug Jenna Kutcher. “Since we are all so comfortable with one another, the photo shoot felt so genuine and unforced—this gave Adam and I a chance to fully be ourselves and goof around,” says Kate. That included photos with their beloved pup Summit, of course. “It was definitely one of the first parts of the wedding planning process where it all started to feel real.”


Britta + Casey

Britta Bengtson and Casey Donnelly took to the great Wisconsin outdoors for their dreamy engagement shoot with Lottie Lillian Photography. Gorgeous fall colors and streaming light created a perfect backdrop for their photos, but it’s the experience that they’ll remember most fondly. “Casey kept me laughing the whole time,” says Britta. “One of my favorite memories came when reviewing the photos. In one, I could remember the exact inside joke Casey was whispering in my ear at that moment—and it’s visible on my face.”


Emily + Steve

Emily Lockery and Steve Kelly hit the streets of Downtown Milwaukee for their urban engagement shoot with photographer Matt Haas. The couple’s chic neutral wardrobe played perfectly against the grays hues of the industrial city center. The best part for the photogenic duo? “Exploring the city together with our photographer and finding fun locations,” says Steve.


I Do (and Don’t)

Achieving swoon-worthy engagement photos is as easy as following a few do’s and don’ts, thanks to our pros. Take note!

Do: Have fun with it. It can be uncomfortable at times to be in front of the camera, but if you’re willing to laugh with each other, you will end up with more natural photos.

Do: Be yourself. “Don’t be someone else, or try to copy Pinterest,” says Matt Haas, of Matt Haas Photography.

Don’t: Try a new hairstyle a few days before the shoot. “Definitely see a stylist to get your hair and makeup done, but don’t make any major changes that you will regret,” says Lottie Royten of Lottie Lillian Photography.

Don’t: Choose a photographer based on price. There’s a reason some photographers are more pricey. Experience and confidence are a must. And beware of friends offering to take photos for you for free to build their portfolio.

Do: Choose a photographer you trust. “It’s important you connect with the photographer, are familiar with their style and choose someone whose ideas align with yours,” says photographer Jenna Kutcher.

Do: Bring a prop. “A baseball bat, kayak, canoe, surfboard, bike, tennis rackets, wine glasses, picnic basket … anything that tells the story of who you are,” says Sarah Spottswood of Spottswood Photography.

Don’t: Put pressure on yourself to have the “perfect” shoot. Nothing about life or photography is perfect, so just be up for anything, show up with a smile and relax.

Do: Enjoy a glass of champagne before your shoot. Not only is your engagement a reason to celebrate but the bubbly can help calm your pre-photography nerves. But it’s best to stop at just one.

Do: Include Fido or Fluffy. Our pets are our families—and involving them in your photography tends to make you more comfortable in front of the camera.

Thematic Elements

Looking for some theme inspiration for your engagement shoot? Here are some favorite ideas from our experts:

  • Iconic pose re-creations: Think classic couples or iconic old photos.
  • Carnival romance: Rides, balloons and cotton candy can be oh so sweet.
  • Take me away: Travel inspiration, featuring vintage suitcases and passports.
  • Glamping: Plaid and thermoses go adorably with canoes and tents.
  • High society: Don your ultra-glam attire in a city or mansion setting.
  • Movie inspirations: It can be anything from The Notebook to Dirty Dancing.
  • Superheroes: Superman, Wonder Woman or other characters can come through in details big or small.

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