Sometimes, a memorable outfit can set the stage for a love story. Let’s take a peek at what these couples were wearing when they first crossed paths—and the lasting impressions those outfits left behind.
Amy and Rick – Together for 8 Years
“It was a night of pre-gaming at a friend’s place when Rick and I first met,” says Amy. “I wore a white tank top, black skirt, tights, and ankle booties. Given that it was January, I probably had a heavy coat on too. My quirky accessories included purple, elbow-length fingerless gloves and some gaudy designer bracelets—somehow, after a few drinks, I ended up wearing a couple of them around my ankles. It sounds chaotic, but I was 23! To this day, Rick remembers those gloves as ‘those strange things you had on your arms.’”
Helin and Dustin – Together for 3 Years
“We connected on OkCupid, and for our first date, we met at a bar,” recalls Helin. “I wore a dress from the Costello Tagliapietra for Uniqlo collection, kept my hair down, and went light on makeup—just a simple cat-eye.”
“I distinctly remember the yellow dress,” says Dustin. “It was really nice, and I thought she looked beautiful.”
Tess and Michael – Together for 7 Years
“It was move-in day for my freshman dorm, and Michael was a senior helping with orientation,” Tess explains. “I wanted to look cute yet laid-back, like a typical college freshman. I wore denim shorts, black flip-flops, a navy Michael Stars long-sleeved shirt, and navy eyeliner to match. Michael swears he remembers me in a white tank top and thinking, ‘This is someone I have to get to know,’ which sounds creepy, but he’s genuinely not creepy at all, I promise.”
Brooke and Eric – Together for 3 Years
“We were on a bus trip exploring Australia’s South Coast with a large group,” Eric recalls. “I can’t say if it was the very first time I noticed her, but it was certainly the moment she stood out. She stepped off the bus, bathed in sunlight, laughing and smiling. She wore cutoff jean shorts and a simple dark T-shirt. What truly captivated me was her radiant smile.”
Danielle and Nick – Together for 8 Years
“We met during a football game,” says Danielle. “I was decked out in black leggings with knee-high Ugg boots that I could roll down in this weird, poodle-like style. My hair had a big pouf, and I felt like I looked amazing. The catch? I was wearing a sweatshirt from his rival school’s team. He hated it, but once we started dating, I ditched it.”
Ali and Jesse – Together for 2 Years
“We matched on Bumble and set up a date on President’s Day,” Ali says. “Since I didn’t have work that day, I opted for a casual afternoon meet-up at a beer hall. I wore a fitted gray long-sleeved tee from H&M, distressed skinny jeans, a floral scarf, and tan booties with a Western vibe. It was casual yet cute without coming off as high-maintenance, even though I kind of am.”
“I honestly don’t remember what she wore,” Jesse admits. “But the point is, she looked amazing, we shared sausages, and we’ve been together ever since.”
FAQs
1. Does the outfit you wear on a first date really matter?
Absolutely! The right outfit can boost your confidence and set the tone for a great first impression. Wear something that makes you feel comfortable and true to yourself.
2. Should I dress to impress or go for comfort on a first date?
It’s best to strike a balance. Choose an outfit that feels comfortable but still shows off your personal style. You’ll feel more at ease, which helps you be your best self.
3. How can I make my date night outfit memorable without going over the top?
Focus on one standout piece, like a statement jacket, unique shoes, or a bold lipstick. It adds a touch of flair without overwhelming your look.
