First Dates Always Lead to a Second When I Wear This

To be honest, I’m kind of a romantic at heart, but I often find today’s dating world to be hard to navigate. In fashion, I’m not often meeting people at work, and online dating apps can be overwhelming, often requiring a lot of work without leading to many great dates. So, when I do have a first date I’m excited about, I want to ensure I feel great, and that confidence often starts with what I’m wearing. Fortunately, I’ve narrowed in on a few perfect first-date outfits that always lead to a second date (when I want one, of course).

One of my go-to outfits is a midi-length dress with an interesting neckline. I tend to go for a dress past the knee because I prefer to skip anything super short. To balance it out though, I’ll be sure it has pretty details on top—like a sweetheart neckline or barely-there straps that make the piece feel special and worthy of a fun date.

My second outfit option follows that same train of thinking. If I’m not in the mood to wear a dress, I’ll instead turn to separates. If I want to slip into jeans, I’ll opt for something like a square-neck T-shirt or a nouveau milkmaid top. Same thing goes for a skirt where I’ll pair a bustier with a slip skirt (again in a below-the-knee length).

I have a theory on why these are such great first date outfits. To me, it’s about what they communicate. They’re equal parts modest and flirty, appropriate and romantic—so they strike all the right notes for a first night out together, in my opinion. Ahead, I’m breaking down some of my winning first date outfits that have led to second dates. They haven’t steered me wrong yet.

outfit option 1: a midi dress with interesting details

This is one of my newest finds and think it will be a date-night staple.

I love that the long sleeves and below-the-knee hemline balance out the deep V-neck cut.

This dress has a flattering neckline and some subtle slits up the sides that make it feel special.

outfit option 2: pants or a skirt + a top with a pretty neckline

I'm in love with square-neck tops, and they're the perfect thing to wear for a casual first date.

I wrote a story about how I always get asked out when I wear this outfit, but it also works as a great first-date look.

This corset-inspired top has quickly become a date night staple.

Shop my edit of more pieces to wear on a first date:

Next: I always get asked out when I wear this one outfit.