Vest: Michael Kors Military-Style Gilet ($149) // Dress: Alexander McQueen Poplin Dress ($196) // Bag: Kenneth Cole Chrystie Satchel ($258)

This look makes all the right moves.  I love the interplay between masculine and feminine styles.  The stylish military very and feminine details like a poppy-colored nail and layered bracelets for a look that is tough but pretty.

The Military Vest. Worn over a dress or belted over a pair of jeans, an olive-colored vest is a great option for late summer/early fall.  This Kors vest has a really cool shape and great details.  I also like this shawl-collar option from Forever21 and this navy, twill vest from Maison Jules.

Plus-size? Try this American Rag military vest.

A Crisp, White Shirtdress. A shirtdress is the epitome of mixing the crispness of a masculine button-up with the femininity of a white dress.  This one from Alexander McQueen is perfect for layering.  Add a vest. Add a belt.  Wear it loose over leggings.

Looking for something more affordable?  This Madewell shirtdress is on sale. Like more structure?  This Fifth Way dress is to die for.

The Structured Satchel. A bag with a strong shape dresses up any outfit.  It brings an easy sophistication that can’t be missed.  It’s the perfect, versatile bag.

I like this Kenneth Cole satchel.  This Rebecca Minkoff Bowery tote/satchel is a great buy at The Outnet.  Need something under-$50?  Try this bag from Urban Expressions.  Prefer a bag in dark brown?  I love this bag from Emilie M.