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What to Wear on a First Date

Updated on April 13, 2014

Gone are the days of the 90s when ripped jeans and flannel shirts were regarded as style statements. It has become essential for men today to dress to impress and even more so if it is their first date. Today’s woman expects their man to be fashionable, well dressed and able to carry themselves well.

What To Wear On A First Date?

What you want to wear may largely depend on the place you are taking your date to. Irrespective of the destination, you would still need to dress well. Remember never to wear clothes with holes or pit stains. How to dress for a first date is a very personal choice. Even jeans are okay provided they are wrinkle free and fit you well. A word of warning, never wear your belt buckle below your crotch or you may not even be seeing your date for the rest of the night. Similarly avoid dirty baseball cap and crooked visor.

Whatever you wear, they should fit you well, enhance your assets and also keep you comfortable, be it jeans or khakis worn over a cotton or polo top, even button down. Avoid ill fitting garments like oversized suits or tight and shiny pants and tops. A proper wear, even if understated will allow you and your date to focus on each other. If you are a T-shirt guy, a plain white, black or gray t-shirt will work well for you, making you look simply stylish. Limit the color of your entire outfit to just two like you can keep the color of your t-shirt, belt and shoes black with a jeans or a pant of different color.

Footwear is also equally important. Sneakers and wingtips are also fine as far as they are neat and polished. Difficult to believe, but your woman will judge you by the footwear you are wearing. Simply put, if you take care of minute details such as footwear, you would well take care of your home and car and later her too!

If your destination is more formal like a chic hotel or a hip club, a theatre or a ballet, naturally a formal dress code would apply. A neutral shaded well fitting tailored suit with a shiny polished pair of shoes is all you need. You don’t need to spend a fortune here. You could get an inexpensive suit off the rack from any downtown fashion store and have it tailored to your needs. Most stores would do that free of cost for you. The key here to look great is tailoring as an ill fitting suit that cost you $4000 will not leave a good impression on your date. Just the one neutral colored tailored fit suit can provide you versatility for your future dates. Wear it over oxford shirt and tie or polo shirt or sweater or just the blazer, T-shirt with jeans will make you look charming.

This is as far as dressing is concerned. Remember to have a good haircut and a clean shave (unless you sport a big or a French beard) along with clean trimmed nails. As far as jewelry is concerned, remember the minimalist look triumphs over heavy garnishing.


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