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Classic: A favorite amongst the It girl and style blogger set, the classic button-up shirt dress is always a chic choice

Underwood was dressed in a pair of stone-wash denim joggers and silver platform high-tops that somewhat resembled an astronaut's bulky moon boots

Cinched waist with boning

The OCBD is arguably the most dressy Outfit 5: More Formal For outfit 5, we went with the wool dress trousers

Two mesh pockets disappear into the pleated skirt and allow for dirt and grit to fall through

The exposed neckline creates a beautiful canvas for statement jewelry, and cool silver tones contrast gorgeously against the warmth of the burgundy fabric