5 First Date Looks That Don't Look Like You Tried, But Totally Fool Him

First dates are tricky. From the location to the outfit, the name of the game is to present your best self without looking like you tried too hard.

But what does that even mean?

Let's start with the place: An activity like bowling is always a safe bet. Having something to do breaks the ice.

The casual, but fun setting allows you to interact naturally, while making sure there are no awkward pauses. (And who doesn't think a gutterball is hilarious?)

When it comes to deciding what to wear, it’s important to ease up on going all-out to the affair.

You want to let your personality and confidence shine through while still feeling comfortable in a sensible choice (read: save the Lady Gaga meat dress for the third date).

Just like an opening line, however, you don’t want be too eager. Remember, your outfit is your first impression -- which is exactly why we ran these first-date looks by real men with real style (and plenty of opinions!).

Between midi- and mini skirts, and fit and flares and A-line frocks, it can be hard to decipher the message your outfit sends.

Which outfits are good for that initial meet and which should be stowed until you’ve gotten down the middle names?

Here's how to put out the "I didn't put any thought into this outfit at all!" vibe -- even if you did, he'll never know.

Here's proof:

The Updated Classic

What we say: Flared jeans are unexpected and sexy, just like you. A simple white blouse rolled at the sleeves reads laidback, while the button down leaves room for some "come hither" cleave.

Tuck in the shirt -- it's important to see a waistline with this cut because it's narrow compared to the wide leg. Accessorize with a statement earring to reflect your personal style.

Not only will you look comfortably cool, but you'll also take pride in knowing you're still wearing just jeans and a t-shirt.

What he says: Ben, a 28-year-old New Yorker, says, "I'm impressed with how she made a work outfit funky for a date. I wonder if she thought about it that morning.

"She's prepared, smart, practical and can do all of that with pretty good taste."

The Playful Pajama Pant

What we say: At first glance, a sharp tuxedo blazer means business, but after doing a double-take, he'll notice you're wearing your pajamas (you can then wisely encourage him to use the correct terminology -- they're, ahem, joggers).

The animal print makes this look more "I'm bringing sexy back" and less "I woke up like this."

If you were doing any less, you'd be wearing long underwear.

What he says: "That's a lot of black," says Mike, a San Fran-based 26-year-old. "but I like it. The pants aren't ones I'd ever expect to see, so I like that she's willing to take risks -- especially on a first date."

The Slinky Romper

What we say: On the inside, a romper is just a pair of shorts attached to a tank top that rides up your FUPA and makes it harder to pee.

On the outside, however, it shows a little skin in all the right places and comes off disarmingly sweet.

That's where the chambray shirt comes in: if you're feeling too exposed, throw it on but leave it unbuttoned, or channel your inner girlhood and tie it at the waist.

What he says: Sayid, a 25-year-old guy from Detroit, says: "She's making good choices. Going with the heels shows off her assets, but it's not being too suggestive or too formal."

The Seductive Sweater

What we say: Yes, there is such a thing as wearing a seductive sweater, and this is it.

This generously lightweight knit means there'll be plenty to ponder (so wear a fuller-coverage bandeau bra). A casual bucket bag complements the tight, skinny jeans.

Because he can't totally tell what's going on under there, he'll be full of questions.

What he says: "I like this one. It's simple. I'd honestly think she just threw this on and walked out," says Houston, 28, from New Orleans.

The Easy Dress

What we say: A breezy tank dress comes across as effortless and still feels fun and flirty enough for a date.

You can effectively show off your toned appendages, comfortably move about and even conceal your midsection, making it the perfect ensemble for bowling and deep-fried bites.

The only thing separating you from your dude is a single layer -- and a few strikes.

What he says: "It's really cool she doesn't shy away from showing me exactly who she is," says Cleveland native, Scott, 26, adding, "I wouldn't want to date someone who felt the need to present a fake version of themselves to me. Instead, I like that she is who she says she is."