What to wear: Date Night

It’s a special day or you just feel like surprising your lady. Never the less today is the day you take out your long time gal or get the guts to ask out the girl of your dreams. Either way, you want to dress to impress!  Your intentions may be good and you might have it all planned out, but it will take a well put together outfit to send the simple date over the top.

Finding the perfect outfit is easy, it’s all about matching your outfit to that special outing. like if you’re going to a play or opera (highly formal) A tux/suit is appropriate, any date that is highly formal will be the easiest to dress for.  If you call ahead and ask most places they will let you know if there is a dress code.  On the other end of the spectrum, a low-key walk through town at night (casual) a pair of dark denim jeans and a lightweight sweater will fair just fine! So take your planned date and categorize it from casual to highly formal.

Casual. An event that doesn’t vary from the day-to-day activities or something that you can get up and do with very little planning. (movie, nature walk, mini golf…)

Semi-formal. A planned out activity, that doesn’t stray from the realm of participating in with a group of close friends/family.  Not too classy or too nice.   (picnic, sight-seeing…)

Formal. An outing that’s very meaningful, involves dedicated planning and thought. Something you would use to show how much that person means to you. (nice dinner)

Highly formal. Super duper! Very high-class and fancy, usually reservations are needed to be made in advance, and there is usually a dress code. The night should be unforgettable. (Theater, opera, horse race…)

Now that you have nailed down what category your date falls under.  You now can go about finding what to wear!

When putting together the perfect outing outfit, keep in mind 3 things. 1. You want the dress between you and date to be on the same level, not to make anyone feel left out. 2. Your outfit doesn’t over exceed the formality of the event, although I’m a firm believer that you can’t be overdressed, in the case of a date,  you could make your lady friend feel awkward if they do not hold that same view. 3. That you feel comfortable in the outfit you choose, confidence is key when dressing for a date.  Now we are going to walk through some each stage of dressing.

Casual.   jeans or chinos are a great option here, with a casual button up, polo, and/or sweater, boat shoes,  canvas tennis shoes, or boots. Really the possibilities are endless here, just find that number one go to outfit you love and rock it! I personally would not go casual for a valentines day date, semi-formal and up is the way to go. You want this person to feel special so put a bit of thought into it, gentlemen.

Semi-formal. Casual and semi-formal go hand in hand here.  You can add to semi-formal a little more like a tie and sports jackets, depending on the event. One thing you will want to upgrade is your shoes, something like a blucher or dress boot will do the trick.  A cardigan, or velvet blazer w/ a pair of dark jeans would be a nice way to dress it up without doing too much.

Formal. Now, this is where you can get more options out on the table. Suits, sports jackets, dress trousers, ties,  dress shoes, bluchers, oxford’s, vests, sweater vests.   You really want to do this well. You want to say that your valentine is special to you! Black, light and dark pink, light blue, red, gray are the main color grouping for the Valentine season. So a light pink button-up with an all-black suit, or gray dress trousers, red button up and a black tie. Mess around with the colors and patterns and I’m sure you’ll come up with a killer outfit.

Highly formal. A tux or full suit is about all you really want to do in most highly formal dates.

Finally, fit!  If you don’t get the right fit, nothing I or anyone says here will help you in the lest.  So get that bad boy fitted And don’t forget to make her feel like the most important person to you, put the phone on silent and complement her outfit. Dress well and enjoy your night!

How a shirt should fit

How pants should fit

How a suit should fit 

Links above provided by Real Men Real Style and Primer Magazine