Style

Going On A First Date? Here Are 53 Midi Dresses That Will Have Him Begging For A Second

Ready to make a lasting first impression? Slip into one of these feminine midi dresses, and we guarantee he’ll never forget the moment he first set eyes on you.

By Anna Hartman1 min read
Beginning Boutique

It’s a universal truth that men can’t take their eyes off a beautiful woman in a feminine dress that hugs her curves in all the right places. They will drop to their knees for the right sundress, slip dress, or bodycon with a just-right slit up the leg. Mini dresses are a bit too suggestive for a first date and can give a guy the wrong impression of what your intentions are. Maxi dresses, on the other hand, can give off too formal a vibe for a simple dinner date or too high-maintenance for a casual daytime meeting. Plus, you do want to show off just the right amount of leg to pique his interest. 

Midi dresses are the perfect little sweet spot in between the two lengths, and, when the silhouette is right, they can have any man begging for a second date. You may be thinking that a dress on a first date can come across as too “try-hard,” and you want to give off more of an effortless air, but that’s where I’d have to disagree. Even for the most casual of first dates (let’s say, for argument’s sake, he’s taking you to a Philly game), you can throw on a pretty white floral sundress with short sleeves and a leg slit. Dress it down with simple flat sandals, “undone” hair, and a clean girl makeup look to match. Rather than using the location as an excuse to wear ripped jean shorts, a baggy t-shirt, and sneakers to blend in like “one of the guys,” this shows him that you value your femininity and respect him enough to dress nicely, but you also don’t take yourself too seriously.

Feeling convinced? No matter how formal or informal the occasion is, there’s a midi dress on this list for every first date, from the coffee shop to the fancy steakhouse downtown. Let’s start shopping!

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