Comparing Josie - a model who has worked hard on her products - to Ivanka - a rich kid raised in her father's conservative business world who was raised to please daddy in his world - is comparing apples to oranges. Ivanka dresses well for the stiff and stodgy business world of her father and is not a model. They are from different worlds - thus different styles.
Josie is beautiful and dresses in absolutely gorgeous clothing that fits her and suits her. What some in their normal everyday lives think of as a cocktail dress is not for someone who is a model and has been all over the world. Her normal clothing naturally would be too fancy for most of us to wear in our unglamorous jobs.
Everyone has different tastes and no one can please everyone.
Josie has some of the best products and what she chooses to wear doesn't change that anyway.