Dress: Dina Bar El Ring: Nordstrom Bracelets: Kate Spade Heels: YSL
"I knew we were going to dinner, so I wanted something classic and sexy, not too short or low-cut, but form-fitting."

Coat: ABA Purple Dress: Vintage Belt: Vintage Necklace: Vintage Shoes: Steve Madden Earrings: Peacock feathers
My directive from Ray Luv was to “dress sexy” so I chose a purple dress that was slinky and tight plus has color. I like wearing vintage clothes so I threw on a vintage belt and peacock feather earrings for fun. I’m a fan of black tights and sexy booties because they go with any dress and the spiked heel booties make anything a little sexier.

Sweater: Forever 21 Striped maxi dress: Aqua for Bloomingdales Necklaces: Good Charma Boots: Uggs
I was really cold after the sun went down, and I wanted something comfy, but slightly dressier than my beach outfit. This Aqua maxi dress is cotton and because it reaches the floor I could wear my Uggs surreptitiously (hehehe). I threw on a Forever 21 sweater from a few years ago, and we were done!

Navy corduroys: J Brand Leopard print sweater: Vintage Tanks: layered, colors from ALC
Since I was in Michigan, and it was cold and rainy, I opted for simple and comfortable. I put on my favorite brown boots, a fun vintage sweater, and I added in a splash of color with colorful tanks underneath.

Jeans: Seven Plaid Shirt: GAP Belt: Colonel Littleton Pink Cowboy Boots: Sheplers
I knew we would be riding horses, so that narrowed down the options to jeans and some sort of shirt. Because I love venturing into costume territory, I decided on my pink Shepler's cowboy boots, which I got for a wedding in Wyoming last summer, and which make me want to sing "Thank God I'm a Country Girl" every time I wear them. I paired them with a basic GAP plaid button down, a rugged belt my ex had given me (Is it weird to wear a gift from an ex on a date with a new boy? Eh. I didn't think so.) and a pink cowboy hat for flair.

Red Layered Scarf: Nordstrom’s Black Cargo Skinny Jeans: J Brand Layered Black Tank Tops: Banana Republic Gray T-shirt: Banana Republic Feather Belt: Vintage Black Wedge Heels: Steve Madden
I chose my most comfortable J Brand cargo jeans and lots of layers so I could take off clothes as needed. You never know when a person’s home is going to be a sauna or have gusts of air blowing through, especially in San Francisco. Since I was doing all black, I like to throw in a bit of color, and the scarf did just the trick.

Blue Jeans: Jbrand Gray Top: Clu Belt: Vintage Black Wedges: Steve Madden
This was one of those rare San Francisco days where you actually didn’t need to layer up or even have a jacket (which I love). I chose the Jbrand flare jeans as a comfortable, casual choice for a walk in the park and the belt added a bit of color and edge to an otherwise long ruched tank top.

Prom Dress: Nordstrom Tiara: vintage Necklace: Ranjana Khan Earrings: Vintage from my mom! Bracelet: Lia Sophia Ring: Nordstrom Pink Heart Purse: Bebe Shoes: Betsey Johnson
Flashback to Prom 1999! I actually wore my senior year prom dress, which had been sitting in a dry cleaner's bag for about 12 years. A few updates to make it a bit more princessy (Why not go all out? A costume is a costume!) included a tiara, a necklace from my favorite jewelry designer, Ranjana Khan, vintage earrings, and an adorable (if somewhat cheesy) pink heart purse from Bebe. And of course, some sparkly Betsey Johnson heels. It was like prom threw up all over me, which is exactly the look I was going for.

Maxi Dress: J. Crew Sandals: Banana Republic
I bought this J. Crew maxi dress to wear to a wedding a few years back and have been looking for an opportunity to wear it again ever since. It's not often you can get away with such a ...large ...dress, but I feel like hostesses for dinner parties can don something slightly bolder than if you were just attending as a guest. Besides, my roommate JP and I had decided that we were going with a theme of blue and white, so it seemed like the perfect combo -- which I paired with pearls for a little WASPy touch. Too bad Andrew's a hipster. Oops?

Blue Jeans: BDG from Urban Read Leather Jacket: Vintage Feather Earrings: From a San Francisco boutique
First date with David on my turf is happening at the end of a work day, so I had to be business/sexy/comfortable. For some reason I was feeling "color" this day and opted for my cobalt blue jeans, off the shoulder top, and my red feather earrings which always add that special something.

Purple Dress: Rebecca Taylor Cross Necklace: Good Charma Black Thigh-High Boots: Anne Michelle
I have a sad fetish for thigh-high boots that has festered since high school. It's sort of pathetic, but they make me feel sexy. In this case, I paired them with a purple Rebecca Taylor dress, cinched with my roommate's belt, and added a cross necklace for a little cognitive dissonance. (Thigh high boots and a cross necklace?! Who doesn't love that juxtaposition?!)

Jacket: Rachel Zoe Jeans: BDG Urban Outfitters Sweater: Vintage Necklace: Gift Boots: Chloe
Another casual day of hanging in the Napa Valley, so I wore one of my favorite colored jeans from BDG for a pop of color amidst a neutral sweater and boots. Threw on one my favorite gift necklaces from a friend with neutral gem stones (or some kind of stones).