The Great Online Dating Debate: Help Me Pick Out My First Date Outfit!

I've picked the guy and set the date. Now if I could only pick an outfit...

Sep 21, 2012 at 1:00pm | Leave a comment

Those of you who have been following my "Great Online Dating Debate" series know how painstaking this process has been for me. (And if you haven't, shame on you. Get caught up here and here and here.) I've hemmed and hawed about damn near everything as it relates to meeting men over the Internet, but at long last, I've finally found a few men that intrigue me, so I'm about to graduate once more and start going out on actual dinner dates. Can I get an amen?

Truth be told, I'm nervous as a hooker in church. I'm guessing that first impressions mean so much more after you've spent weeks wooing someone with your wily words and your perfect profile pics -- obviously I want to live up to this amazingly captivating online persona I've built. I've got my hair and makeup looks down pat; now I need to decide what I'm going to wear. Here's how I normally dress:

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That oversize scarf? She's EVERYTHING.

But my signature personal style (which I've dubbed as "dressed-in-all-black-like-the-omen") doesn't exactly convey what I want to say, which is "potential wife" at best, or "arm candy" at the very least. I'm mean, it hasn't worked for me thus far, so it's time to change things up a bit. Below, four fabulous looks I can totally pull off. Wanna help me pick one?

Option #1: Slick and simple and sexy

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I pretty much live in skinny leather pants, but I usually wear them with high top sneakers and a black t-shirt. If I go for this particular look, I'll sub in a black pointed-toe pumps and a white silk peplum blouse. Still comfortable, plus it's very 'office badass' which describes me to a tee.

Option #2: Funky fresh, dressed to impress, ready to party

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I'm not the biggest fan of pencil skirts in the traditional sense, but when it's covered in a colorful funky print and paired with a leopard clutch, a cropped tee, and slightly slutty red pumps? Yes, muthafucking ma'am. That's how you rock a pencil skirt.

Option #3: Prim and proper in peplum

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He doesn't need to know that I have a mini-FUPA just yet. That's where this posh peplum dress comes in. It's rare that I look all polished and put together like this -- it'll be like I'm playing dress up. Kind of excited about this one!

Option #4: Serving straight body, a.k.a. B-A-W-D-Y

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What good are my crazy curvy proportions (size 8 waist with size 12 bust and hips) if I hide them? I should probably put them on front street and show off the goods, right? Of course with this look, I'll have to wear three pairs of Spanx. Yes, three -- the first pair sucks everything in, the second pair smoothes out any leftover lumps, and the third pair vacuums it all up and serves as a little extra insurance. With a bodycon dress you can't be too careful.

Clearly, I put way more energy into my primping than I do my pimping. Anyway, what say you?

Tell me below in the comments, or over on Twitter at @IndiaJewelJax!