Putting Your Best Foot Forward: What To Wear On Your First Date

Published on Author GG RayLeave a comment


We’ve all been told how important making a good first impression can be. That advice is good for just about any situation, especially a first date. On a first date, you want to be sure that you put your best foot forward, but knowing what to wear on a first date isn’t always that easy. Should you dress casually? Should you dress up? What will the other person be wearing?

Because you aren’t the only one out there who asks these questions, and because it’s not always clear what you should wear on a first date, we’ve brought you this informative article on the ins and out of what to wear on a first date, no matter what the occasion.

The Biggest Mistakes

When you are going on a first date, you really want to avoid making a clothing faux pas:

  • Don’t wear sneakers on your date – even if you are going to a casual location, you might go out to a bar or club that has a dress code, and they might not let you in with sneakers.
  • Avoid wearing a baseball hat, unless you are playing baseball on your date.
  • Avoid sports paraphernalia – This means no sports caps, no hockey jerseys and no basketball shirts.

The Blind Date

The blind date is probably the most difficult date to plan for. First of all, you don’t even know the person. Second, if you don’t know the person, you don’t have any inclination as to what they might wear. Third, you want to look good, but you don’t want to be overdressed or under-dressed.

Before you panic, keep in mind that the other person is probably having the same questions and doubts. If possible, you should try to at least have a conversation with your blind date or share an email. This way, you can decide what you are going to do on your date and dress appropriately.

However, in case this is not an option, you should keep the following advice in mind:

  • Wear comfortable clothes – If you feel uncomfortable in the clothes you are wearing, you will look uncomfortable, and this may ruin your date.
  • Wear confident clothes – Choose something that you know you look good in. This confidence will bode well on the blind date.

Having said that, don’t show up on pajamas (comfortable) or a tuxedo (fashionable). Unless you know where you are going and can judge what you should wear based on that, pass on the denim and choose a pair of dress pants (no pleats!). Pair that with a long-sleeve shirt with a collar and you’re pretty much set. This can take you anywhere you want to go, from a casual restaurant to a club to a martini bar for drinks later on.

An Afternoon Date

When your first date has been planned for an afternoon, you can dress more casually. Let’s assume that you are doing a Saturday lunch date or a Sunday brunch date. Choose something a little more casual than what you would wear for an evening date. For example, black is a formal color and something that many people fall back on for evening affairs.

For an afternoon date, choose khaki pants, Capri pants, or even a nice pair of jeans. You can pair that with a short sleeve shirt with a collar and nice leather sandals. This outfit will be perfect for lunch on a summer date. In this kind of outfit, you can go from having lunch, to window shopping, to a walk in the park. Plus, you can almost rest assured that for a summer lunch date, she will be wearing a flirty summer skirt, so you can choose an outfit that will nicely complement her outfit.

An Evening Date

Most first dates tend to take place on weekend evenings – Friday and Saturday nights are the most common nights for dates. The good thing about first dates, as opposed to blind dates, is that you have already spoken to your date and you will have decided where you are going for the night.

If you are going out for a fancy dinner, then you should absolutely wear a jacket, but to avoid looking stuffy or too “dressed up,” you can probably avoid wearing a tie. That way, if you end up going to a club later on for drinks and dancing, you won’t feel out of place at all.

On the other hand, let’s say you are going to a casual dinner and a movie. You can certainly wear jeans for this type of date, as long as they are nice, clean and well-fitting. The days of torn, dirty jeans are gone and the days of expensive, tailored denim are here. Pair your jeans with a long sleeve collared shirt – in fact, this type of shirt should be a staple in all men’s wardrobes.

Other Tips On Preparing For First Dates

There are a few things you should remember when getting ready for your first date:

  • Haircut – Prepare for a first date like you would for a job interview. Start by getting your hair cut. Looking unkempt and greasy isn’t going to get you laid, unless you are a rock star.
  • Smell good – While telling you shower, shave and apply cologne may seem silly, you’d be surprised at how many first dates are ruined by body odor or just plain disheveled guys.
  • Take care of your eyebrows and fingernails – You don’t have to go out and get a manicure (but it wouldn’t hurt) or get your eyebrows waxed (and that wouldn’t hurt either), but you should make sure your nails are clean, trimmed and look nice. Also, get rid of that unibrow so you don’t look like a Neanderthal!

Just Look Your Best

As long as you look your best, smell nice, and are dressed appropriately, you should really have no trouble with dressing for a first date or a blind date. But if happen to be one of those guys who just can’t get it together, then you should call up a female friend and ask for help!

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