Engagement Photography Guide
Couples pose for engagement portraits in Milwaukee and the surrounding area.

Engagement Photography Guide

Alright, so you’ve signed up for your wedding photography which includes an engagement portrait session as part of the package. There are a lot of great benefits and uses to having an engagement session. You’ll get used to my style and be more comfortable with me for the wedding portraits. You can use the photos for save-the-dates and invites. Or you can just celebrate and remember your time together dating.

With all that being said, I wanted to give you some tips and things to think about to make your engagement session great. This will be a comprehensive list, so please don’t be intimidated with all of this. I’ve had some couples opt for simply meeting at a park for an hour and taking photos that make them look photogenic and nothing more. We can keep it as simple as you’d like.

Choosing a Time of Year

Whether your session is simple or more elaborate, the first thing you’ll need to think about is when you’d like to take your photos.

Many couples get engaged during the holiday season either during Christmas and New Years, but they may not want to get photos done in winter.

Beside the overall look you’ll want in the photos with the background, choosing warmer weather is more comfortable, but if you have stylish coats, scarves and hats, winter can make for beautiful portraits. Plus, the cold weather can give you a reason to snuggle.

Many Wisconsinites prefer the fall colors for their engagement, but the weather can be unpredictable and since fall is my busiest time of year I can’t offer any weekend sessions and rescheduling can be dicier if I don’t have any other open dates.

Every season has its benefits and downsides, but many couples choose their season based solely on the logistics of their wedding date.

You may want to use the photos for their save-the-dates and invites. Save-the-dates go out a year before the wedding and the invites are mailed six months ahead. It’ll take me about five weeks to finish all of the edited photos, plus you’ll want time to choose your photos and design the invites, so that’d be either eight or fourteen months before your wedding.

Time of day and length of session

My engagement sessions are two to four hours long. That’s a longer amount of time than a lot of other photographers offer, but I love setting up portrait sessions and this gives us time to go to different locations, wear different outfits and even set up themed portraits.

All of these sessions are scheduled for the best light, which is either in the morning starting before sunrise or in the evening ending at sunset.

If you choose one to three locations we’ll plan on a four hour session. If sunset is at 8 pm then we’d start at 4 pm.

If you choose only one location we’ll plan on a two hour session, meeting at 6 instead of 4 pm.

Locations

Choosing locations is ultimately up to you, although all of my engagement sessions will be locally in southeastern Wisconsin unless we specifically agree on something else before you sign your wedding contract.

However, most people ask for suggestions and my favorite places.

We typically choose a public place that doesn’t charge for photography, many times a city or state park. If you have a place in mind that does charge a photography fee, it will be your responsibility to pay it unless I specifically choose that location.

I also suggest picking a variety of locations. 

If you really like an outdoor park with rustic woods, we’d then couple that with a beach location and a place in downtown Milwaukee. At the very least, I like to suggest picking an urban spot and a nature spot.

For nature there are woods, fields, the beach and by the water. For urban, there is downtown with skyscrapers, the lakefront, or a trendier neighborhood feel like the Third Ward or Cedarburg.

Outfits

Similar to locations, I suggest a variety of outfits, but only up to three so we don’t spend all the time during the session changing between clothes instead of taking photographs.

With three outfits you can choose a dressy outfit, a casual outfit and then one that shows off your personality.

The personality outfits can be clothes that show off your hobbies. I’ve had couples wear Wisconsin Badgers gear, their college alma mater, their club baseball team, camping gear, or Milwaukee Home T-Shirts. It can also just be clothes that are a little more adventurous like a big floppy hat, a floral patterned t-shirt for the guys or that vintage outfit you found at Goodwill. If we’re meeting somewhere unique like an arcade bar in Milwaukee or a neon-lights flashing ice cream drive-up restaurant, a more bold and loud outfit would work well for these spots.

Other than that, you can try to match your outfits to the locations. Dressier outfits work best in the city and the more casual outfits work better with nature. Barefeet and shorts work best for the beach and sweaters and boots work better walking through the trees during the fall or winter.

With any outfit, think about using layers and accessories to make the outfit pop.

Themes

If you’re excited for an engagement session and ready to take advantage of the full four hours, you can use a part of that time doing a themed session. This won’t be the entire session, just an hour or two supplementing the more traditional engagement portraits. 

The theme is up to you, but most of the time it’ll involve your hobbies. I’ve had baseball fans bring bats, balls and uniforms to the baseball field. I’ve had bicyclists bring vintage bikes. I’ve had travelers bring cameras and suitcases. I’ve had campers bring a tent and set up a campfire. Others have set up a picnic (with my help). And, still others have brought their pets to the session.

The picnics are the most common and they work great for engagement portraits. However, I love being creative and am always looking to stretch my photography if you have ideas.

Props

The last thing I’ll bring to your mind is whether you’d like to use props. Aside from a themed session, some couples like to bring a prop. At the very least, this can be your engagement ring. Otherwise, some people like to bring something with the wedding date on it: pumpkins in the fall, coffee cups in the city or a life preserver on the beach.

As always if you have any questions or would like to talk through your choices, please feel free to give me an email at matt@bigskyphoto.com or text or call me.

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