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Engagement Session Outfits

CONGRATULATIONS on your engagement! Seriously! It is such an amazing moment in your life that only happens once, soak it all up. If you want more information on getting in touch with me, you can head on over to!

One question I get often is, “What do you recommend we wear for our engagement session” and well I wish this was a simple answer, it really is not. Which is exactly why I decided to make this blog for all my clients and for anyone looking for some assistance in this area. (I have a huge announcement regarding this topic SO soon).

(1) One dressy, one more casual.

For my clients, I give them two outfits for their hour and a half session to ensure we get enough content in each outfit. Of course if they want three, I just let them know that their total photos delivered will more than likely be less. If they still want three, I typically roll with it.

I recommend one more dressy choice and one more casual choice. Now you are probably like Okay Bailee that is great, but what does dressy and casual even mean!? I was there once too – I GOTCHU.

Before getting in so deep on what I mean by dressy and casual, if you find that you are NOT a dressy type person and would prefer two more casual options (or vise versa), please wear two casual (or two dressy if that is what you are into) because at the end of the day I want these pictures to look and feel like YOU. Not only from the posing/prompting I do based on getting to know you but within outfits as well.

Dressy outfits don’t have to mean heels, a long skirt or whatever you were initially envisioning when I said dressy. When I say a dressy outfit, I am envisioning a long flowy dress with cute shoes and maybe I would bring a hat to throw on for a couple shots. Another example would be with a long skirt and a cute graphic T tied or something along those lines. Embrace your style just think about flowy and long.

(2) Picking Colors

I always, always – no matter the season – recommend earthy tones and darker colors. Olive green, rust, burgundy, tan, beige, taupe, black, darker blues, etc. They photograph really well and make your photos the most timeless they can and will be.

Avoid pastel colors! Anything that reminds you of easter, ABORT MISSION! If you really like yellow though, you can choose a mustard color rather than a pastel color. Mustard is a great choice! Pastel and lighter tones make your skin tones not nearly as nice as darker colors. They also don’t make the photo look as great as it could with my style of editing!

(3) Don’t be afraid to accessorize!

Feel free to wear no hat for some pictures and add a hat to others. Hats really finish a look and I personally loveeeee them! They are a simple add to make the same look, look like another look completely. I love felt wide brim hats for ladies!

I have three different hats, but my favorite hat is from a company named Gigi Pip. They are expensive, but they are 1000% worth it if you will wear it. They are super high quality and will last forever – seriously! Plus they ship in a super nice box with lots of padding so you are sure to get a hat that looks just as it did before shipping.

Some other accessorizing options are jean jackets, scarves, cardigans, etc. Basically layering pieces are always great options. You definitely don’t have to add anything to your photos, I want them to still feel like your photos!!

Stores to Shop From:


  • Willow and Roan – casual, functional options
  • Bohme – dressy and casual options
  • Baltic Born – dressy
  • Pink Lily – casual (SUPER cute sweaters!)
  • Roolee – cute tops (mother and me options here as well)
  • Altar’d State – more expensive, but cute options


Want more information on what booking me for your engagement or wedding photos looks like? CLICK HERE!

Engagement Session Outfits

bailee raye

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