I have had a decades-long fascination with the Sinatra clan, which began when I fell in love with Old Blue Eyes when I was six years old. Frank Sinatra was the first man that I ever had a crush on, and as most of my delusional crushes go, I assumed that I would one day marry him. Well, he unfortunately passed away before I ever had the chance to make that happen (and I swear that's the ONLY thing that stopped it because I still think Frank and I would've gotten along swimmingly), but I still pretend that I am part of the Sinatra family. For some reason, despite loving her music, I haven't really written too much about the most 60s-centric of the lot, Nancy Sinatra. I really have to thank a commenter who suggested I write about her, because going back through her music and looking at pictures and reading about her life has really sparked something in me! 
In my opinion, Nancy is one of the most underrated fashion icons of the 1960s. Obviously, her look is influential today -- as even Lana Del Rey refers to herself as a self-styled "gangster Nancy Sinatra" -- but why isn't every girl marveling over her fab looks? 
We all know that she had boots that were made for walking, but some other style signatures include bright, tight minidresses, colorblocked tops, cigarette pants, and oversized sweaters worn as tops. I read on The Fashion Spot that Nancy is 5'3'' but the way she dressed -- in her short hemlines and tall, heeled boots -- her legs looked as tall as skyscrapers!
Her look is what I would consider an Americanized version of the yé-yé pop look, and I think that is also the best way to describe her music style as well. The crossover between Nancy and French pop is incredible (please do yourself a favor and check out the French cover of "Boots" by Eileen, called "Ces Bottes Sont Faites Pour Marcher"). There is a fun French feel to her look, a mix between the sweetness of France Gall and the bombshell-ness of Brigitte Bardot, but also a lovely flower child element à la Sharon Tate (this photo is so amazing!). 
Even in a pre-(500) Days of Summer universe, my karaoke song of choice was always "Sugar Town," but only recently did I learn that the song was about LSD. How crazy is that?! I love learning facts like that about songs. Also, I think Nancy is the unrivaled queen of the cover song -- I love her versions of "As Tears Go By," "Here We Go Again," "It Ain't Me Babe" and the Beatles tunes "Run for Your Life" and "Day Tripper." She makes even Lennon & McCartney all her own!

Title: from "Some Velvet Morning" (Nancy Sinatra & Lee Hazlewood)