Engagement Pictures

I thought we had a month for this. We planned on early the morning of Columbus Day, and we had time to choose the locations & figure out what we were wearing.

The engagement pictures don’t really matter to me, but were one of the most important things to Mike, so I am trying to take them seriously. This means I’m basically trying to microplan something I never even thought about. By tomorrow. Which at least means the weather forecast is out, and it isn’t warm.

Luckily, they seem to consist of basically two things:


We need to figure out what to wear. Most things that fit me well* are a couple years old, and the things that aren’t are work pants or busy patterns. I love a good busy pattern, but I hear that isn’t the right choice for engagement pictures. I did like the idea of wearing something monochromatic but with texture, and a scarf for a pop of color was a common suggestion (although it won’t work for me–Mike hates scarves).

I think we’ll change once, and these are the basics I’ll look for. Of course, due to none of my clothes fitting all that well, we need to go shopping today to find the things on my list. Wish us luck!

For Her: Casual For Him: Casual

Simple top


JeansHenley or Polo

Flip flops or decent shoes?

For Her: Dressier For Him: Dressier
Casual dressStill a cardigan?

Fun tights (its cold and I like tights)

Low heels

Khakis or dress pantsButton down shirt

Dress shoes

*This is both a comfort thing and a style thing–if my clothes actually fit, I won’t look squeezed into them, which will make me look thinner than barely fitting in to a smaller size.


We want to reflect some Chicago in our pictures, although it can be on the subtler side. When we met, Mike lived on Michigan Ave, so we’d love to get his old building (its the one with the “beehive” on top near the Art Institute) in the background. We got engaged at my church, but since we’re getting married there we didn’t want to do engagement pictures there as well.


  • Lily pond in Lincoln Park
  • Northerly Island
  • Promontory Point
  • Lakefront (anywhere along the path)–maybe
  • Lincoln Park (by the pond)
  • Lurie Gardens (Millenium Park)
  • By the Nature Museum (in the Ravine out back)
  • Art Institute Gardens

Chicago Love:

  • Michigan Ave by river
  • Daley Plaza
  • Art Institute (front, bridge)
  • Skyline at Plantarium
  • Buckingham Fountain
  • Navy Pier (we’re obsessed with the swings)
  • Union Station
  • Wrigley
  • Millennium Park (the bean)
  • Harold Washington Library
  • Conservatory (Lincoln Park or Garfield Park)
  • Chicago Theater

City Feel

  • El stop/train
  • Lightology
  • Underpass to Lakefront trail
  • Rooftop deck
  • Graphic hotels

I checked out this post for ideas, as well as posted on Weddingbee for help! How did you figure out what to wear? Where to go? So many options!!


One thought on “Engagement Pictures

  1. Pingback: Engagement Pictures: How to Stare Deeply Into Each Others Eyes | Mary Marry Mike

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