You got your fresh new haircut, confirmed the dinner reservation and maybe even picked up some flowers. Yep, you have a date with someone special, and hopefully didn’t neglect the most important detail: what to wear? Sure, lots of men will tell you, “Oh she doesn’t care how I dress”, but rest assured she does. Sticking with the same old jeans and collared shirt is an easy and lazy habit to fall victim to. Fortunately, I have three foolproof strategies below that are sure to ease the process and guarantee some special attention.
We all have a rebellious alter ego that sometimes itches to escape, and this look will let you indulge your wilder side, while perhaps paying homage to Danny Zuko in Grease – minus the shiny pompadour. While this may seem uncharacteristic from my usual style, for me there’s really nothing that comes as close to evoking the inner badass than a rugged, well-appointed leather jacket.
The beauty is in the simplicity of the formula: fitted leather moto jacket, henley shirt, slim cut dark jeans and Chelsea boots. The button opening on the Henley shirt broadens the chest and accentuates the modern tab collar on the jacket, which is what gives a moto jacket its unique edge.
Tip: leather jackets should fit snugger than you think, or else your date might think you borrowed your dad’s leather jacket from the 80s.
These days, dressing up for a special dinner has a funny way of elevating the night into a proper occasion, especially when you’ve been eagerly anticipating that Michelin star tasting menu you had to book months in advance. The extra effort to show your date that you can clean up like a dignified gentleman, and more importantly that you want to, is sure to be met with delight.
Try combining a bold patterned sport coat, dark separate trousers and a tonal cardigan to bring out your dashing, sophisticated side, but without the stuffy office aura. The cardigan, similarly to a waistcoat in a three-piece suit, adds a dapper layer of intrigue and formality, while the knit tie brings a muted geometric texture to add some interest. A pattern suit would also work well as an easy alternative.
Shoes should preserve the dressy-leisure theme, and some slick Italian loafers definitely check all the boxes: polished, carefree and a little laidback.
When you need something versatile this approach strikes the perfect balance between sharp and casual – an ideal choice to make a lasting impression on a first date. A sharp navy sport coat with an easy cut speaks for itself, and imparts a relaxed elegance. As a friend of mine likes to often remind me, you never want to appear stiff or look like you’re trying too hard on a date. A casual chambray shirt and chinos will keep everything dialed back accordingly.
A date is never the time to slack off on your shoe game; some even say that shoes are the first detail about a man that a woman notices. My shoe of choice here is the classic Adelaide oxford in a vivid color.
Don’t be afraid to try something new. You may just sweep her off her feet.
What is your favorite date night look? Share your thoughts in the comments below.