Both pairs of shoes go with every outfit so you are welcome to just choose one to bring :)

Pictured is your gray J. Crew pencil skirt and white woven lafayette blouse.  A white silk blouse may also be worn.  

The classiques cowl neck dress is pictured on the bottom row. The plum blazer can pair with any of the dresses. The navy velvet blazer pairs best with the tweed and gray dresses. 

The green Everlane blouse may go under the the black J. Crew skirt suit or the green MM La Fleur dress.

Charcoal Theory jacket pairs with the gray theory turtleneck dress. The navy Theory suit pairs with the black Boss top and the patterned dress.

Jacket is optional over peplum blouse (business casual look)

Black J. Crew Skirt Suit & Navy Theory Skirt Suit

Tights are optional.