I have a pretty casual yet classy style of dressing. I never buy anything too trendy or revealing and dress fairly conservatively. If I want a date to know that I'm looking for action, I believe it's best for my personality, wit and wandering hands to communicate that, not my outfit. That said, I have been known to sport some cleavage now and then.
Below is a smattering of my date outfits, starting with the summer. You might notice the progression from meatball to SlimJim in these pics, as I dropped almost 15 lbs since then. You might also notice that my hips are here to stay. Awesome (sarcasm font) but at least they're more toned now. And yes, these pics have all been through an Istagram filter. I've found that Instagram "Amaro" lightened up these pictures perfectly. I'm also too cheap to get Photoshop and everyone knows Instagram makes you look like a model.
This pic is from the summer on a date with DJ (I wrote about him here and here). I was probably overdressed because he liked to wear graphic tees and cargo shorts and take me to dinner buffets, but at least I looked cute. He's 6'2" so I rocked these 4" wedges on almost every date.
|Dress: Old Navy, Wedges: Anne Klein|
|Blouse: Joe Fresh, Pants: American Eagle, Necklace: Stella and Dot|
I wore this shirt with jeans out on a date with a litigator from Match.com. He was nice enough, aside from the fact that I felt like I was being interrogated all night. We went on two dates but there was no chemistry. We shared dating horror stories over beers. He also blogs but declined an offer to guest blog. He spent 20 minutes lamenting about how gets depressed living in NYC because he isn't part of a couple and has no one to go to brunch with on Sunday mornings. It was like that How I Met Your Mother Episode where Marshall and a man friend go on bro dates for brunch.
|Top: Gap, Pants pictured: Gap, Jeans worn: Banana Republic|
Do you remember Mr. Big, the foot fetish guy? As is sometimes the case, he came with more drama than I posted about. He tried to weasel himself back into my life this summer so I met him for lunch. It was one of those "You could have had this but didn't because you're a douchebag who drives an expensive car to compensate for your, um, shortcomings" type of dates. We had lunch at an upscale restaurant and I wore this dress. The picture doesn't do it justice but it hugs my curves in just the right way, so that when I sashayed my ass out of the place, leaving him to go home alone, he was cursing himself. Every woman needs a dress like this.
|Dress: Banana Republic, Shoes: Aldo|
I wore this outfit on a Wednesday night to meet a guy from Plenty of Fish for drinks. He was normal and cute and we hit it off. He had a great sense of humor but after a second date, I realized that under the sarcastic facade, there wasn't much else.
|Blouse: Old Navy, Jeans: Banana Republic, Necklace: Stella and Dot, Wedges: Payless (don't judge me, they're awesome and comfy)|
I wore this outfit on a second date to the movies. I don't like the movies and have no idea why I agreed to a second date at the movies. Even worse, my date wanted to see the Twilight movie, which was surprisingly good (shirtless werewolves make any movie better). My date thought that the previews were a good time to kiss me for the first time. Oh yeah baby, slobber on me in a crowded theater full of teenyboppers. Needless to say, it was a last date.
|Blouse: Old Navy, Jeans: Banana Republic, Necklace: Stella and Dot, Wedges: Payless|
I wore this for my first date with Thunder Thighs. We went to a restaurant and got drinks. It was an awesome first date, but the proceeding ones weren't as good. I've actually had a lot of luck wearing this top on dates. I also wore it on my second date with Batman.
|Tank: Old Navy, Cardigan: Target (I have it in black too, love this cardigan!), Jeans: American Eagle|
I have no idea when I wore this outfit but if I say it was a first date out for drinks I would have about a 95% chance of getting it right. Apparently I was going for a biker-chic look.
|Tank: Old Navy, Jeans: Banana Republic, Jacket: NY&Co, Necklace: GroupDealz|
I'm a huge fan of cowboy boots but rarely wear them out on dates. I broke them out for dinner on a rainy night with a restaurateur I saw a few times. He's from Virginia and doubted my ability to pull off cowboy boots. I proved him wrong. I paired them with an off white lacy tank top and a ruffled cardigan to soften the look.
|Tank: Forever21, Cardigan: Banana Republic, Jeans: American Eagle, Boots: J.B. Dillon|
|Tank: Old Navy (yes, same as the biker-chic look), Sweater: Gap, Jeans: Forever 21, Boots: Sam Edelman, Purse: Onna Ehrlich|
|Top: Old Navy, Pants: Banana Republic, Necklace: Stella and Dot, Bracelets: Francesca's from years ago|