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Especially for the gentlemen: What to wear on a first date

Posted on 09 October 2008 by Nick Roberts

A couple of days ago, when I was talking with several of my friends about the topic, they had informed me that people do not really go on dates anymore, which I am kind of sad about; so guys, we should bring dating back. When we do bring dating back, what are gentlemen to wear? This can be a daunting task! I remember last year, several of my residents came up to me and asked me the question, “What should I wear?” Well in deciding what to wear for the date, a gentleman should dress for what the occasion calls for. With that in mind, I came up with three looks, which can be applied to the majority of dating scenarios that college students go on.

Casual—Polo, jeans and sneakers: This look is probably the most commonly used and easiest outfit in the male college student’s repertoire, but it can also be done wrong. To start with, make sure the polo fits well. I see lots of guys whose polos are too big and could probably go down a size. The polo’s sleeve should end at the mid-part of your bicep, and not all the way down to your elbow. The fit should touch your body from your shoulders to waist without binding. The jeans should be fully intact, no holes or paint marks or whatever else Abercrombie throws on them, and preferably straight leg. Your sneakers should be clean, not beat up, and if were to suggest a pair, they would be a pair of white Chuck Taylor’s. That shoe goes with just about anything.

Nice Dinner—White button down dress shirt, dark jeans and dress shoes: Every gentleman at this age should own a white dress shirt, and you can get a lot more mileage out of it then just wearing it to church/wedding/job interview. For the fit of the shirt, the tail of the shirt should be long enough to lay under your rear end, but not too long if you choose to wear it untucked. The cuff of your shirt should fall in the crook between the base of your thumb and wrist. The buttons should lie flat when buttoned and the fabric should not bunch. If you have a slimmer frame, go for shirts that are usually labeled modern or slim flit, or if you are on the larger side, look for shirts that have box pleats on the back of the shirt. This allows you more room but without the excess fabric. If the weather is getting cooler as it is now, wear a v-neck sweater if you have one, preferably in grey. As for the jeans, again straight leg is the way to go, with no holes and other markings, and keep the denim dark, which is a little dressier. Lastly, as for the dress shoes, black or brown is up to you, just be sure to match your belt with it, and please no white athletic socks.

Swanky Dinner/Bar or Special Evening—Sport coat, dress shirt and dark denim: This look is if you are going some place fancy but a suit is not required, or this look could be substituted for a suit. For those men who have a suit and normally only wear the jacket with the pants, this is a way to get more use of out your jacket. By wearing the jacket with a dark denim jean you still can achieve that formal effect, but without the uncomfortable feeling that some gentlemen have when it comes to wearing a suit. To finish the look, pair it with a pair of dress shoes or even a pair of sneakers, but like I said before, make sure they are in great condition. Add a pocket square if you wish to add a little more flavor to the ensemble. There is a great video online at men.style.com that will show you step by step how to do this, or just check out my blog, where I will post the video.

So there are three fail-safe looks when going out on a date. These are just some guidelines; so don’t feel obligated to do exactly what I wrote about. The great thing about fashion is that you can make it your own, so experiment a little and come up with a look that feels good for you. As Tim Gunn from Project Runway says, “Make it work!”

Please visit my newly created blog Make it Work Milwaukee. On my blog, I will post pictures of people who I think display an individual and creative sense of style which visitors can comment on, as well as my articles from The Warrior and any additional topics that I feel like writing about.

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