What To Wear On First Dates

We asked, they answered! Fashion experts and authors offer tips on what will make the right impression, clothing-wise, for both men and women — and outfits to avoid at all costs.

By Mark Amundsen

on’t wear clown shoes on the first date.” That would seem to be a pretty solid rule, right? Ah, but what if your date is someone you met in clown school? Hmm? Well, then, clown shoes might not just be completely appropriate — they might even be de rigueur. This style business is more complex than you thought!

Whether you’re a man or a woman, you want to make a great first impression on dates. Of course, we all
It is always better to be over-dressed than under-dressed.
want to be loved for both our finer innate qualities and our physical attributes, not just for being a snappy dresser. But what we wear says a lot about our personalities and our day-to-day lives, too. Good clothes may have no effect on a date, but bad clothes almost certainly will.

So, what to wear… or avoid at all costs? Women can poll friends with mixed results, depending on those friends’ taste and ability to stay objective while being emotionally supportive (and still giving you an honest critique). Guys usually only know other guys who are just as clueless as they are, but can save themselves some embarrassment by checking a restaurant’s dress code, for example (jackets and ties might be required), or picking a date that requires a certain type of clothing (camping, a trip to the beach, or other activity dates practically dress themselves, so to speak). We asked some fashion experts for some helpful tips to help keep you sartorially superb and feeling confident on your first date.

Classy Equals Confident
“It is always better to be over-dressed than under-dressed. Especially on first dates; if you go somewhere where others are a bit more casual than you, if anything you will feel a bit ‘cooler’ and your date will be impressed.”
— William Squire, host of Your Signature Style

“The one piece of advice I would give is this: If you are meeting someone for the first time, wear something that makes you feel good and confident! The best way to make a great first impression on a date is to leave your ‘crazy clothes’ in the closet. We all have an outfit that is fun, silly and reflects our personality. But a first date is not the best time to show it off! If you’re worried about being either too dressy or too casual, you should go with a business casual outfit (something appropriate for the office). Additionally, do a little research. Don’t hesitate to call the venue and ask what guests visiting the establishment typically wear.”
— Steve Kemble, lifestyle guru and member of US Weekly’s Fashion Police

Women’s Wear Dately
“Accentuate your best asset so that you can control the focus. Wear a fitted turtleneck or dangly earrings to bring attention to your face. Believe it or not, a form-fitting turtleneck can be very sexy and chic. If your best asset is your bust, then wear a V-neck top or wrap dress. If it’s your waist, wear a belt. Wear skinny jeans, pants, a short dress or skirt to show off your legs. But don’t wear all loose-fitting clothes; if your top is blousy, then wear a fitted bottom for balance.”
— Odessa B., proprietor of Nobody Jones Boutique, a haven for cheap chic in Los Angeles, CA

“No low-cut tops that make you — and others — forget you are a lady. It’s not going to make a great first impression if you are falling out of your blouse! Don’t wear anything that is too tight or needs constant readjusting; it’ll make you both feel uncomfortable.”
— William Squire

Just for Men
“Guys need to understand that the first date is absolutely the time to avoid extremes. The
Remember to keep accessories to a minimum.
leather-studded collar and cowboy boots should stay home in the closet. If you’ve never worn a leather jacket, vest, or put gel in your hair, this is not the day to start. This is also not the time to start creating a new ‘look’ or ‘persona.’ The key here is keeping it simple and classic.”
— Ellen Rakieten and Anne Coyle, authors of Undateable: 311 Things Guys Do that Guarantee They Won’t Be Dating or Having Sex

“Your daily uniform — jeans and T-shirts with a nice long-sleeved shirt, worn loose over the undershirt — is a great look for many occasions. But not for everything. Remember, jeans were created to wear to work in the fields and milk the cows, so no matter how much you spend on them or how much you dress them up, they are still jeans! For something a bit more fancy, try a nice pair of slacks with a sweater or shirt (tucked in, of course). Most men also look great in a turtleneck; it’s very James Bond-ish.”
— William Squire

The Formula for Formal Events
For women: “If the date is for a big recurring event, look online for posted pictures to see what people wore in the past. If the affair is more formal, go simple with a long black dress. For cocktail hour, go short (but comfortable). Remember to keep accessories to a minimum, like earrings and a bracelet or earrings and a necklace.”
— Odessa B.

For men: “If it’s a formal event, ask if it’s black tie. If so, a good quality tuxedo is the only way to go. Please stay with a traditional white pleated shirt and simple, tasteful studs and cufflinks. BLACK SOCKS ONLY! If it’s formal but not black tie, you can never go wrong with a great navy blue suit paired with a nice blue, striped or checked dress shirt and a pair of loafers or formal shoes. Stay away from thick-soled walking shoes.”
— Ellen Rakieten and Anne Coyle

Casual Chic
For women: “For more casual events, never leave your comfort zone. If you don’t wear jeans, then don’t make an exception. Going casual usually reflects more of your personality, but you want to look polished and appropriate. Always wear a heel with your casual look.”
— Odessa B.

For men: “If it’s casual, you never need to go more casual than a great pair of cargo shorts, a polo shirt with a collar and flip-flops. No Crocs, please. And stay away from running shoes unless you’re actually going to be running or hiking. White socks in any of these situations are NOT ALLOWED.”
— Ellen Rakieten and Anne Coyle

My Date’s In An Hour! What Should I Wear?
For men: “If you only have an hour, I would suggest first and foremost that you concentrate on being neat and clean. Your personal hygiene says a lot about who you are. Additionally, keep it simple by wearing your favorite outfit versus trying to impress someone with a new outfit that you are not accustomed to wearing. You don’t want to look uncomfortable.”
— Steve Kemble

For women: “First, pull out your favorite outfits. One of them is bound to fit. Second, pick out your sexiest (comfortable) shoes and work your outfit around them. Third, tap into your feminine side with a dress. A dress is always good because it is one item that you can dress up or down with a boot, a jacket, pumps or a shawl.”
— Odessa B.

Mark Amundsen is a writer and editor in New York who is working on a book about acute, chronic slovenliness, its diagnoses and cures.
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