What to Wear on a (First) Date

In today’s world, men can no longer get away with looking unkempt. In the decade of grunge music and baggy clothes, called the 90’s, men got away with wearing ripped jeans and flannel shirts and calling them “fashion statements.” Even the runway showed the influences of the Seattle sound. But those days are long gone, and in their wake we are left with a complete reversal. With Queer Eye’s popularity and the emergence of the “metrosexual” as the new trend for men, today’s man must be ready to dress to impress, particularly on a first date.

clothes to wear on a dateThe women of today expect a man who knows how to dress. Women care for themselves, and expect the same for their other half.  Women also tend to judge a man on his appearance on a date. The clothes you wear can make or break a romantic interlude, so it is wise to dress accordingly. Remember that your date is likely spending hours selecting an outfit. It will behoove you to spend more than two seconds grabbing a T-shirt out of the “clean” pile on your floor.

The first thing to think about when dressing for a first date is, of course, where you are going. But one golden rule is that no matter how casual your destination, looking clean, crisp, and put together cannot hurt. Even if you are just grabbing a slice of pizza or playing miniature golf, you should dress neatly. Do not wear clothes with holes in them or novelty T-shirts with pit stains, unless a life of celibacy is what you are after. Jeans may be fine for the occasion, but be sure they are wrinkle-free and that they fit well. If your belt buckle is below your…ahem, crotch, you should not walk out of that door. You are not Kevin Federline (nor does your date want you to look like him). Do not wear a dirty baseball cap or a crooked visor. Women want to gaze into your eyes, not the logo of the college you went to 10 years ago.

Wear clothes that fit you well and show off your best assets. A well-fitting pair of jeans or khakis with a cotton button down or polo (also well-fitting) will show off your shape and flatter you, regardless of how buff (or unbuff) you are. Huge and oversized is not the way to go, nor is the too-tight and shiny approach. A simple, understated outfit allows your date to concentrate on you and not get her heel caught on the hem of your oversized basketball jersey.

Nice shoes are also a must. Whether you wear sneakers or wingtips, be sure they are clean and polished. Many women judge men by their shoes, which sounds silly, but is very true. A man, who takes care of his appearance, including a “small” detail such as footwear, is likely to take care of his apartment, his car, and in the future, her!

If you are going to a more formal location, such as a chic restaurant for lunch or dinner, a hip club for cocktails, or the theater or ballet, a more formal dress code naturally applies. A nicely tailored suit and tie in a neutral shade such as navy or charcoal gray and a smart pair of shoes will have you looking the part of Mr. Right in no time. Even if you do not have the finances for a closet full of Brooks Brothers or Saville Row suits, you can get an inexpensive suit or sport coat and have it expertly tailored to fit you. Tailoring is the key to looking great, because even a $4000 suit will not look good if you cannot button the jacket or see your hands beneath the sleeves. An inexpensive suit can look posh with the right adjustments. With one suit you can have a variety of looks for future dates by altering the Oxford shirt or the tie that you wear under it. You can even pair the pants with a polo shirt or sweater, and wear the blazer with jeans and a T-shirt. There is a lot of versatility in a suit, and it can take you on dates for months to come.

Another thing to remember when getting ready for a first date is that you should get a haircut and be sure to shave (hey, you never know if a kiss or something more may lie in the future). Be sure your nails are trimmed and clean. Little things can separate you from other men, and give you an edge towards getting a second date with your dream girl.

The key to dressing for a date is to let your personality shine through. If you have a funky style, an off-the-rack suit may not be right for you, but a vintage velvet jacket could be perfect. And if you are a buttoned up businessman, a playful look may not feel like you, and so you should wear something in which you feel confident and comfortable. Balance is the key to looking great. If you balance your personal style and the appropriate attire for your destination, you are sure to have many successful dates to come.