linen purple dress Boden Women's Florence Blend in This breastfeeding Elowen 27 | Lace Linen

These tucks are a nod to modern design sensibilities, adding a touch of uniqueness to the classic ballgown shape

The Little Black Dress If you could only have one dress in your entire wardrobe, let it be the little black dress

Once you add the dressing, things will start to turn mushy pretty quickly

Structured Drape Twill Satin kaftan dress

"Whether you are wearing a clunkier sneaker like the New Balance 740s or a simpler framed sneaker like the Converse All Star Sneaker, you can work your way up," says fashion stylist Talya Bendel

Polished leather shoes would just be a touch too formal, so the addition of the suede double monks punctuates the look perfectly