One of the most common questions I get when scheduling a photo session (particularly an engagement session) is, "What should we wear?" I've suggested color schemes, jeans, heels or flats based off of the location we had chosen, but really, when I heard this answer from another photographer, it made total sense:
Wear what makes you feel beautiful. 

I looked back at the photos that Gerard and I have had taken for our anniversaries the past 3 years and it's true. I migrated towards what I loved to wear and what made me feel beautiful.

Anniversary #1:
Location-Wisconsin at a friend's wedding, another friend pulled Gerard and I aside for 10 minutes and got these. I love these capris and have never found a replacement.  And the top made me feel glamorous despite its polka-dots....

Anniversary #2:
Location-a field across the street from our photog's house. The owner of the land kindly let us park on his grass. I had just taken the hem out of these jeans to make them longer and they have side pockets in the style I prefer. I love how comfortable they are and I love the white top I chose-a little ruffle, but still business-like. We dressed Gerard accordingly. And added our '49 Pontiac and 9 week old Ella.
 (photos 2009, courtesy of Nick Nielsen)
Anniversary #3:
Location: a field on our route from our home to Des Moines. I found these brown pants for $4 at Kohl's clearance rack. Score! I had also just purchased this green top with a lacy collar line-just the right amount of feminine for me. I scheduled a hair cut for me and for Ella (not from the same person!) so that we'd be trim and fresh. I felt gorgeous. And we dressed Gerard accordingly.

 (photos 2010, courtesy of Justin Meyer)
If you wear what makes you feel beautiful, you will "shoot beautifully". 

If you wear what makes you feel confident, you will come across confidently in your photos. 

Your creativity, your personality, your sense of style, will come across so much better if YOU direct what you wear to a session instead of me. 

This will forever be my advice when asked what to wear for a session-because it's true and it works!

Happy clothes hunting/shopping!