I wanna take a minute here to coin a very important fashion term: The Shepherdess Dress. I'm pretty sure I came up with it, because I had never heard it before. So I want to make sure it's out there on the Internet that the Shepherdess Dress appellation is MINE.

Why is it so important to me, you might ask? Because a Shepherdess Dress is what I wore on our first date with Sasha. And he clearly thought I was crazy. Also, I hate to say it, but he might have been right. At the time, I called it a sheep keeper dress. But I have since then learned that the proper way to call a woman who keeps sheep is a shepherdess. Look at me getting all sophisticated and shit.

I'll go more in detail about our first date below, but first I feel like I need to identify what really makes a Shepherdess dress. Because it has a few distinctive characteristics. The most important one being that it has to be off the shoulder, preferably with a big flounce. It also has to be tight at the waist, and flowy on the bottom. So no body-con dress can qualify as a Shepherdess Dress. Bonus points if it has pockets, buttons, or a belt at the waist. Lastly, it should be in a light shade (or white), with bonus points if it's in a fine stripe or gingham pattern. Basically, you want the dress to look like a modern, non-costumey version of Betty Bo Peep.

The one I'm wearing in these pictures is the perfect representation of a Shepherdess Dress, and so are the 12 (!) dresses below. (Keep scrolling until the end of this post.)

It's quite similar to the OG Shepherdess Dress I wore on our first date with Sasha, which is why I bought it in the first place. I mean, I had to. I couldn't leave the "Sheep keeper dress 2.0" at the store, I had to bring it home and give it some love. If you want to see the original version, here it is. I know, not exactly the type of dress one would wear to a first date, right? At least not what I would typically choose, for sure.

But the circumstances of our first date were a little special. First, it was a miserably hot summer day. And I had a meeting with a real estate agent right before (I was putting my condo on the market). So I had to look professional enough to be taken seriously, but I obviously didn't wanna show up to a date in a suit. I also didn't want to wear anything to sexy. The first part of our date was at his place, so I thought a revealing outfit might push him over the edge if he was a date rapist. A girl's gotta cover her bases, you know?

So I figured the original Shepherdess Dress was the perfect choice. It was breezy enough that I wouldn't suffocate, dressed-up but not too much for day-time, and cute but not sexy. I also had to cancel our initial date (2 weeks before the actual thing) at the last minute, and showed up to his place almost an hour late due to traffic and road work (I got lost)... So I figured if he still wanted to bang me after seeing me for the first time in a dress fit for some kind of farmer girl, he was a keeper. Because let's be honest here, if a man doesn't want to have sex with you after a first date, there's probably not gonna be a second date... And same goes for women.


So it might have been a risky choice of outfit, but I went for it anyway. Way to keep the bar low on a first date, right? Since he later admitted that he kept looking at my chest to "try and figure out if I had tits" (LOL), I feel like it was the perfect choice of dress, in hindsight. I guess that's partly where the saying "Keep 'em guessing" comes from.

And that's the story behind the Shepherdess Dress. It was the dress that witnessed the most amazing first date of watching a World Cup football game (Hungary against Germany - and we lost miserably) fuelled with sushi and champagne, before heading over to a rooftop terrace in Old Montreal, for more food and drinks. It lasted for hours, and it was basically two dates in one. Two amazing dates, I gotta say. And since we talked about the dress so much (after I casually apologized for wearing something that made me look like I just came out of a field) he still remembers what I wore to our first date, 2 years later. Way to look like the most attentive, observing man ever, ha!

What about you guys? Do you remember what you wore on your first date with your significant other? Would you wear something like a Shepherdess dress, or would you stay away from it? Let me know in the comment section below, I'm dying to know!

Love, Jenny xx