So you've finally done it. You've surpassed the fear of rejection and landed an opportunity to impress the woman you picture yourself next to. Outfit selection should fall second only to determining the date activity on your list of priorities. I assume, as a gentleman, that you want to show this woman why you'd make a good choice of partner; so a design intent is defined.
Now, your date night outfit should convey several things with the most important being that you respect the time that this beautiful woman is investing in you. Regardless of activity, your outfit should resonate with the words: classy, masculine, and comfortable. By designing your outfit with each of these design parameters in mind you're reinforcing this woman's opinion that you have many admirable character traits.
I mention the word classy first in the list of design parameters because it demonstrates maturity and respect for oneself and ones company. A classy man is one that doesn't flaunt his muscles with overly tight tailoring, or his money with label ridden clothing. Instead, a classy man will choose well fitted clothing that is not loud in and of itself but when combined as an outfit will exude effortless sophistication, think well tailored suit jacket and clean shoes. A tolerancing error here will be catastrophic, gentlemen; make sure each piece is well fitted and clean. For those of you who haven't figured it out yet, women often gauge how serious they will treat men, especially suitors, based on how clean they keep their shoes. Don't believe me? Ask any woman in your life. More unspoken rules will be covered in the future Design Intent segment, "Passing the Sh*t Test."
The second design parameter is by far the trickiest, ones outfit must be masculine. Masculine clothing is commonly workwear inspired; earth tones, olive green, brown leather boots, and durable fabrics. Though this rugged aesthetic could be part of your personal style these traditional blue-collar inspired pieces should be avoided, or their use minimized, in a date setting. Instead, masculinity can be conveyed using fit. A perfectly fitting shirt should accentuate the broadness of a mans shoulders, and the drop to his waist (however minimal). Pants should lightly taper and end as not to bunch around ones ankle, in this way demonstrating a sleek but dimensional leg. Furthermore, a canvased blazer will couple with the well fitting shirt to perfectly highlight ones shoulders, while streamlining the waist. In total, well fitting clothing will make you seem taller, thinner, and broader. With these tips you can show her off while also subtly demonstrating she's dating a true gentleman.
The final design parameter is comfortable. This parameter is quite often forgotten in pursuit of the first two parameters. I caution you, do not sacrifice the ability to swallow or breathe for an overly tailored shirt, especially when also wearing a tie. If your outfit is not comfortable, or perhaps not appropriate for the situation, it will be very clear to your date that something is bothering you. Inevitably this will make her question whether it's something she is, or isn't doing. This design parameter should be tested an hour or two before the date. Once dressed try walking around, going up and down stairs, and most importantly, sitting down. If your outfit passes each test and fits your chosen date activity all that's left is to sweep her off her feet. If you figure the perfect method to do so, please, write it below in the comments and help your fellow gentleman out!
Also... BRING HER FLOWERS.