Don’t know what to wear on a first date? Matchmaker and founder of LastFirst, Emily Holmes Hahn, shared her tips on picking the perfect date-night outfit based on the real feedback she gets from her clients — find out what your date is really thinking when they see your outfit.
First date jitters can be stressful enough without having to overthink your outfit, but the truth of the matter is that what you wear definitely contributes to your date’s first impression. Don’t know where to begin? Well, we’re here to help take the pressure off getting ready. We consulted matchmaker extraordinaire, LastFirst founder Emily Holmes Hahn, who decoded what your date is actually thinking when they see your outfit — ever wonder what your clothes say about you? Well, for starters, the best thing you can do is wear something you feel comfortable and confident in — believe it or not, a first date is not the best time to break out your trendiest new outfit that you have yet to wear. In fact, you’re better off sporting that go-to LBD you have hanging in your closet, and here’s why.
What does your outfit say about you?
“I tell clients that your first date outfit can speak louder than words! Did you come straight from work (or worse- the gym?), or did you invest a little time to go home and change into a head-turning ensemble? Pulling together a fashionable and occasion-appropriate look indicates how seriously you are taking your date, and yourself. By putting visible effort into your outfit choice, like matching accessories and a chic pair of heels, (you’ll get no sympathy from me for foot pain), you are showing your date that you are excited to meet him!”
What general perceptions have men and women shared with you over their date’s outfits?
“I think the main thing about outfits that both sexes usually perceive, is simply how much effort is put into them! It’s sad to say, but most women who have shown up on a LastFirst date in loungewear or sneakers, (the men always tell us), have not gotten a second date. On the flip side, it’s still surprising to me how many men comment to me on their date’s outfit, if they liked it! Oftentimes they then cannot describe what exactly their date wore, but the sentiment is there! First impressions are everything, and in today’s world of mindless swiping, it’s crucial for girls to set themselves apart from the masses of singles out there. A thoughtful and flattering outfit is a great way to do this. The same goes for men, though women tend to be more detail-oriented. I often hear things like “He was wearing such a cool watch,” or “I noticed his shirt had a little monogram on the sleeve”- the extra effort does not go unnoticed, guys!”
Any colors/prints/patterns trends you think are great for dates?
“Always go with the color that flatters YOU the most! This is not the occasion to wear the newest pastel shade if it washes you out. Black and white are usually lovely on everyone. An ultra-flattering, but equally comfortable, LBD or LWD is my personal go-to for a night out. I’d stay away from patterns for first dates, as they can be so hit-or-miss, but if you really want to wear one, I’d recommend a classic stripe or simple floral print, rather than something super loud.”
Any colors/prints/patterns trends that are major no-nos for dates?
“Again, I think the only color/pattern ‘no-nos’ are the ones that don’t suit you or that you don’t like! Additionally, anything that you think might be ‘too trendy for him to get,’ is probably, yes, too trendy for him to get.”
Could you be too trendy on a first date?
“Definitely. Stick to something tried and tested. You should know what works well for you; it should be something you are comfortable in, something you feel fabulous in, and something on which people have complimented you, more than a few times! That said, if you love fashion and feel best in something au courant, keep it sexy, elegant and feminine, rather than wearing an androgynous, edgy or overly conservative trend.”
Tips for accessorizing for the first date?
“LastFirst matchmakers constantly quote Coco Chanel in saying “before leaving the house, a lady should look in the mirror and remove one accessory.” It’s so true! While it’s essential to put on those finishing touches to complete a look, there’s a fine line between ‘just enough’ and ‘too much.’ Additionally, if you are drawn to big, bold or trendy accessories, limit yourself to one. Stick to a bracelet, bag or ring- as huge earrings or a flashy necklace can be distracting and even off-putting on a first date.”
What should you always bring with you on a first date?
“A positive attitude and genuine curiosity about the other person. Humans are amazing creatures, and if you go into a date truly open to experiencing someone new, you’re sure to have a meaningful encounter, even if it’s not a romantic one. As for aesthetics, bring a little “signature” something that is uniquely you, that might spark a good conversation. For example, a meaningful piece of jewelry, a keychain with a family photo, or quirky cell phone case.”