Date Night Style

Posted on December 11, 2017 by Daniel Ocean

Dating can be fun but it can also be a stressful mind-fuck. Whether you’re a seasoned dater or just getting back on the scene, the experience can be a little nerve-wracking. The truth is, what if you are actually about to meet the person that is going to change your life. Like, forever? Sure there’s a collection of men out there that are simply on the hunt and ‘forever’ isn’t in their vocabulary but I think most of us approach dating with an open mind. That meeting someone fun to hang out with is healthy but the prospect of meeting someone you’re crazy about is…real. Welcomed even.

“The truth is, what if you are actually about to meet the person that is going to change your life.”

Ok so you finally asked the person out. You’ve creeped their Insta, FB, LinkedIn, even their Myspace from 2002. You’re ready to meet. Probably the most common style tip phone call I get from my buds is this exact scenario. What the F should I wear on a first date? Because here’s the thing…there’s alway a lot of unknowns on the first date. You don’t really know know your date’s style, you don’t always know exactly where you’re going, whether the date is going to start from coffee to dinner or dinner to late night drinks. So you need to be versatile. Mature, fitted and versatile.



1| Shows respect.

Time has never been more valuable and when someone is giving theirs to you, respect it. Chivalry may have a faint heartbeat but the idea that a man should present himself well certainly is not.

2| Physical attracts matters. Always.

Not much else to say here…No matter whole wholesome, smart and witty we are, putting a twinkle in your date’s eye is never a bad thing. Attraction is huge on a first date and it can be the glue in the future after you’ve spent 45 minutes in the car arguing about whether you should paint the walls eggshell or pearl. Sometimes it can end a fight and start an afternoon of stress relieving lovin’.

3| It show you are a grown up.

We can have a playful personality but every woman or man wants to date a big boy. A guy with a purpose in life and a guy they can introduce to their bestie, parents or boss at that future holiday party.


Dating is about confidence. If you walk in and you’re feeling good, you’ll be yourself. Your date will sense it, likely be relaxed by it and in turn, be themselves. That should at least set the tone for a good time and that’s what dating is all about. I always say my sense of style revolves around the perfect fit and this outfit is no different. We want to let our personality be the star, not our outfit so keep it simple and don’t try too hard.

“Black jeans are always the perfect place to start.”

1| The perfect black denim

Black jeans are always the perfect place to start. Avoid the ripped ones for date one so  invest in a solid clean pair that can navigate through brunch cafes or chic restaurants uptown. Try the Zara Basic Skinny Jean

2| The classic + fitted top

So there are two ways to take this look. For the athletic guy who wants to subtly showcase his frame, aim for a premium tee with a stripe or minimal print. Make sure it’s a fresh one off the rack or give it a good steam. Remember, fitted not tight. The second look is here is a classic knit jumper. It’s masculine, cozy and gives off an aura of friendliness and maturity. Good tees can be found anywhere from Abercrombie to J Crew to MR PORTER.

3| The killer boot

Your boots need to be fresh so if it looks like you’ve been climbing trees in yours, get a new pair, bro. You can’t go wrong with a leather pair with a buckle, a suede Chelsea or a classic pair of desert boot from Clark’s. They say a woman ALWAYS notices a man’s shoes and I believe. It’s another small opportunity to broadcast that you pa attention to the details and you’re mature enough to have a handsome pair of boots. Love these gum-bottom Chelseas from Aldo.

4| The handsome watch

This is crucial. Like the entire theme of this outfit, we want to show we have style but that it doesn’t define us so choose a sharp but not ostentatious timepiece. Make sure it fits and isn’t dangling down your wrist. Thomas Sabo has a great collection of watches for men like this one.

5| The smell of love

The final touch…your fragrance. Rule 1, don’t wear too much. The idea hear is that you should wear just enough that if and when your date nuzzles into your shoulder at the bar, in the uber home or on the steps as you say goodbye, they can experience your scent. Something masculine and memorable. I vote for the new warm scent of Armani Code.

6| The jacket

Always go minimal with your outerwear. A solid coloured bomber is always a good option that is sharp, mature and comfortable. Having a bomber instead of a long coat allows you to keep it on comfortably for those quick coffee dates in the cafe. Check out this one from Topman.



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