What I Wear on Dates

In my last post I mentioned that I went out on a date and was wearing one of my favorite "causal yet sexy" blouses from Old Navy that I love so much.  I haven't posted pics on here for a while after a hilarious attempt by my ex-husband to get me to take this blog down which caused me to go quasi-incognito, so I thought it might be time to share some of my (headless) go-to date outfits with you.  That, coupled with the fact that I need to start clearing out the 1,463 selfies from of my iPhone camera.  Don't worry, I have a head in real life, I'm just refraining from posting it on here (and because my camera doesn't let me get a shot of both my head and my shoes so I've been opting for shoe shots).

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

I wore this outfit on a date with a guy named Eric from Match.com.  It was nothing to write home about, so I didn't.  We had a nice time grabbing drinks at a local upscale bar and then played pool at his blue collar men's club down the street.  He was probably the only man belonging to the club who had never worked an hourly wage job in his life.  It was a fun date but he never contacted me...possibly because I beat him in shuffleboard and wasted his money playing country songs on the electric jukebox.

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)

If you're thinking this outfit looks similar to the one above, you're right.  It's the exact same thing except the shirt is teal (looks blue in the photo but it's teal in real life).  I freaking love these shirts. They're from Old Navy, wash and wear well (except for the one I had in purple that got a hole in it) and show enough cleavage while simultaneously hiding a post-beer muffin top.

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

Afternoon dates are good too.  Not only does it save calories from alcohol (black coffee please), but they're easy to squeeze in and low pressure.  I met a web designer turned photographer out at Starbucks a couple of weeks ago.  I was going to my volunteer commitment afterward so my outfit needed to be cute enough for a date but casual enough to get snot and glitter on because I volunteer with kids.  The date was fair, worthy of a second if he hadn't been such a sad panda about his ex-wife cheating on him and his house going into foreclosure.

Tank: Old Navy (yes, same as the biker-chic look), Sweater: Gap, Jeans: Forever 21, Boots: Sam Edelman, Purse: Onna Ehrlich

This is the "casual yet sexy" shirt that I mentioned in my Date with a Gay Guy post, although this isn't the night I wore it.  I know this because I recently dyed my hair dark brown and, as you can see, I have blonde hair in this pic.  This is probably a pic from another date.  Since these are my go-to outfits, I sometimes wear them more than once.  Different people, different places, shhh don't tell that I wear repeats! Anyway, I love this shirt (so much that I have it in an orange color that for some reason I've never worn) because it's soft, falls nicely and has a sexy satiny feel to it.

Top: Old Navy, Pants: Banana Republic, Necklace: Stella and Dot, Bracelets: Francesca's from years ago

So there you have it, pictures of me and an idea of what I look like as I'm wow'ing potential life partner candidates.  You may have also realized that it's possible to make cheap clothes look good.  I'm all about not breaking the bank while getting free meals and drinks.