Roscoe Village Engagement Session Featuring Oly the Pup – Madeleine & Justin

I had so much fun with Madeleine and Justin during their Roscoe Village engagement session last fall! When I first heard from these two, they had recently moved to the neighborhood with their pup Oly and had just started planning their 2023 wedding… which just happens to be one month from TODAY!! Needless to say, I cannot wait to capture their wedding day!

Our session began with a lovely walk around the neighborhood with Oly. We passed by the iconic Welcome to Roscoe Village sign on our way to one of their favorite local spots, Four Moon Tavern! After a couple brews, we headed home for some photos in their Oakland A’s apparel on the steps (Oly too!). I have to admit: these are some of my favorite photos from our entire session! I mean, just look at that sweet puppy face!

As the sun began to set, we headed east to the lakefront for photos with the skyline. Madeleine and Justin had gotten engaged at the lakefront earlier that year, which made it extra special! The way these two laugh together made my job super easy – I truly felt like a third wheel (in a good way)! We even rented an impromptu Divvy bike to make date night complete 🙂

Madeleine and Justin: Your Roscoe Village engagement session was such a blast… I can’t wait for your wedding day next month!

Candid photo of couple laughing with their dog in front of fall foliage during Roscoe Village engagement session
Romantic fall engagement photo of couple with their dog in Roscoe Village neighborhood
Fun photo of couple walking their dog in Roscoe Village neighborhood during fall
Couple holds their dog near ivy wall during fall Roscoe Village engagement session
Candid photo of couple in front of fall foliage during Roscoe Village enagagement session
Candid engagement photo of couple walking dog across street under Roscoe Village sign
Exterior photo of welcome sign in Roscoe Village over Wolcott Avenue street sign
Candid photo of couple sitting under Four Moon Tavern sign during Roscoe Village engagement session
Black and white photo of couple drinking beer at Four Moon Tavern during Roscoe Village engagement session
Close up photo of couple clinking beer glasses at Four Moon Tavern during Roscoe Village engagement session
Photo of couple with their dog at Four Moon Tavern in Roscoe Village during their fall engagement session
Couple sits on steps of house with dog during fall Roscoe Village engagement session
Candid photo of couple sitting on steps with their dog during fall engagement session in Roscoe Village
Candid photo of woman smiling with dog on steps during fall engagement session in Roscoe Village
Candid photo of happy couple with dog during fall Roscoe Village engagement session
Candid photo of couple wearing Oakland Athletics hats on steps with dog during fall Roscoe Village engagement session
Candid photo of couple walking along Chicago lakefront during fall engagement session
Black and white photo of couple walking along Chicago lakefront during fall engagement session
Fun photo of couple at Chicago lakefront during their fall engagement session
Fun photo of couple walking along Chicago lakefront during their fall engagement session
Romantic photo of couple in front of Chicago skyline during fall engagement session
Candid photo of couple kissing during fall engagement session at Chicago lakefront
Romantic photo of couple in front of Chicago skyline during their fall engagement session
Woman rides away on Divvy bike while fiance playfully chases her during their fall Chicago engagement session
Black and white photo of couple riding on Divvy bike together during Chicago fall engagement session
Candid photo of couple on Divvy bike with fall foliage during Chicago engagement session
Candid photo of man carrying fiancée during fall engagement session at Chicago lakefront
Romantic photo of couple kissing in front of Chicago skyline during fall engagement session

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