long layered dress When You Know Patchwork Maxi line prom dress designed to make you shine Alana Crimson Red Tiered Evening

While Y2K fashion may be in its comeback era, we think this romantic vintage-inspired corset bodice and lace trim will always be in style

In the 1988 comedy Working Girl, Melanie Griffiths character Tess McGill best personified the look and the battle for women to get ahead with her big-shouldered, tailored jackets

It wasnt necessary to wear a blouse under a suit jacket but was often more comfortable

Currently wearing Dress c/o Macys [HERE] | Earrings, Collection by Joya [SIMILAR] | Headband, BCBG [SIMILAR] | Shoes, c/o Diba True [SIMILAR] | Purse, Rebecca Minkoff [HERE] I have a hard time styling dresses with thigh-high boots, but I think the black dress / black tights / black boots combo works well here

Outfit #1 Small Town Street Scene Lets start with the iconic small town street scene outfit