Tips for Chicago Engagement Sessions- from photographer Brittany Lynn

I get these questions a lot: What should I wear? What should I bring? Where should we go? I hope this post helps you decide the details!

First, remember why you are doing engagement photos. You are celebrating the engagement between the two of you and practicing getting behind my lens before the big day. You want your session to represent your personalities and relationship between both of you. You are going to use these photos for save the dates, maybe a guest book, favors, and to hand around your home.   Here are a few things to consider when planning:

What season is it?

If it is spring, then a location with blossoming flowers are hands down the best. I love May because of the blossoming flower trees! Usually the trees will have shades of pinks/reds which photograph beautifully. They are usually only alive for a short period of time, so it’s important to catch it on time! The majority of my brides always want a fall engagement session, which realistically in Chicago only lasts for about….. a month. The weather in September is nice, but the trees don’t start turning until mid-October. By the end of October, the trees are gorgeous, but remember usually the weather is MUCH colder and windier (which means your gorgeous curls that you spent an hour on may be flying everywhere!). So it’s time for you to decide which you prefer- to brave the cold to get better fall colors, or call it safe and do it while the weather is a little nicer?  I do get a few brides who will bundle up and put on their winter gear for a December or January engagement session, and let me tell you I LOVE snowfall photos! It can be sooo beautiful :)

justin & emily blog (25 of 25)


Once you know the season you want to do, the next step is figuring out a location. I usually tell my brides to break it down between the city or the suburbs. If you want a Chicago Style engagement session, then the hot spots are always great. Millennium Park, Lincoln Park Zoo, and the Planetarium to name a few. These all have fantastic skyline backdrops for photos and iconic Chicago spots. If you want more of a urban session, Pilsen or the west loop has some awesome murals and street art to work with. Remember when traveling in the city it is usually best to meet at the first location, and cab it all together. Finding parking and walking just takes up too much time!

If you prefer a more rustic setting- the suburbs could be better. There are some fun barns in the southwest Homer Glen/Lemont area, the rocks of  Waterfall Glen in Darien, and various downtown settings which can be fun (LaGrange, Riverside, Naperville, ect). Cantigny Park in Wheaton is just stunning year round ($35 permit fee). The Morton Arboretum is a perfect spot in the fall to get a variety of colors and trees ($75 permit fee, and pesky mosquitos in August/September). There are plenty of other spots that could be closer to your home, and don’t forget the places which are meaningful to the two of you. Do you frequent a restaurant or bar often? Are you avid readers? Having a variety of stops makes for fantastic photos!

David & Sarah Engagement (95 of 112)53Brittany Lynn StudiosWhat do I wear?!

I always recommend that my couples wear two outfits, the first should be comfortable and the second should be more formal. The casual outfit is great for certain poses, like having your guy pick you up or if you are going to lay on the ground. Dresses can be restrictive, so I always recommend that one outfit isn’t a dress. Jeans or leggings matched with cute boots are a perfect combination. Don’t forget to ACCESSORIZE! Scarves, jewelry, make sure you plan out the whole outfit carefully and that you feel comfortable. If something it too tight or the shirt is too short you will be self-conscious the whole time! Also don’t forget to make sure you have on proper undergarments (no bright bra straps showing through a lace top!). The formal outfit is always fun to end with, to get some sassy night time photos. Most guys keep the same jeans on and just dress it up with a button down and a blazer (they have it so easy). Girls, don’t be afraid to go big with a flowy dress or floor length cocktail dress if you are doing your session in the city!



Most couples try incorporating their wedding colors, but remember not to be too matchy-matchy. Now that you know what season it is, carefully think about what type of backgrounds there are going to be. If you are having a fall wedding with reds and oranges, and also doing an October engagement sessions your outfit may blend in too much with the trees. Complimentary colors tend to photograph nicer (blues/purples pop nicely with fall trees). Bright colors always look fantastic in the spring, and if you are doing a winter session you don’t want to wear white and blend in with the snow :)

Todd+Amanda Engagement (26 of 146)


Lots of couples are turning to DIY or etsy to get some cute banners made with their wedding date on it. This is a fantastic idea for your save the date, but there are other creative ways to do so as well. Jerseys, pumpkins, athletic stuff (hockey sticks, balls) are also great alternatives. And also don’t forget your pets!! My dogs are my family too, so why shouldn’t you bring them with? (Maybe not the whole session, and if you have a friend who can be the dog handler that would help greatly!) Anything else that shows your relationship feel free to bring along, wine glasses, books, flowers…… <3 (Eugene has an extensive hat collection that is off-limits to Tara, which inspired this picture)

I hope these help in the planning process, and of course feel free to ask about specific questions!

Rustic Engagement Session, chicago illinois (33 of 35)








La Grange + Destination