Wear something that makes you stand out. If there was ever a time to strut your stuff this is it. Why? Dressing to impress can impress your date in more ways than one. Obviously, showing that you put some thought into your look tells your date that you want to look your best for her.
Go all peacock with the colours. Unskilled dressers think “dress to impress” they immediately pull out every bright colour and loud pattern they own and try to put them all together into one intense outfit. The result is one hot mess of a look that reeks of trying too hard.
Kill the sartorial pyrotechnics. Most guys look their best with a maximum of two colors in their outfit. Some simple patterns are optional, but varying textures is mandatory. You can mix things up with a textured knit tie and a smooth sharkskin suit.
STYLE TIP: We say break away from the board room look and go with a lighter colored suit that you can wear night or day and is a little unexpected, like this Light Blue Gray Sharkskin.
YOUR ‘GO TO RESTAURANT’
Put on a jacket regardless of the temperature. In between dressed-up and casual lies the blazer and this is the perfect time to put one on. It sets the tone for your whole outfit.
Jackets can take many forms from the classic solid navy blue to a check, herringbone, windowpane or houndstooth. Because they only cover your upper half, a blazer can feature a more outspoken pattern. Contrast solid chinos or dark jeans with a patterned jacket and you’re already two steps ahead of the competition.
Wear a jacket that should be a part of a full suit. If you’re going to wear a pinstripe jacket, wear the matching pants and always throw on a tie.
While a solid jacket can work, we advise against going with an ultra-conservative solid gray worsted wool for a blazer. While you can get away with a gray suit jacket as a blazer, it’s not going to win you many style points.
STYLE TIP: This looks stays casual by featuring classic sport jacket elements (the houndstooth pattern and classic casual shirting)
THE ‘DINER’ DINNER
Wear a gingham shirt. Many guys take casual overboard. Adding something as simple as a collared shirt to your look is all you need to step up your style, but there is a right and a wrong way to do it.
Gingham shirts have taken the office by storm in recent years as they’ve been paired with suits on the pages of just about every men’s fashion publication. But historically gingham was reserved for more casual environments.
Take gingham further down the ladder of dressiness by going with a two-colour version. Two colour gingham shirts, like their flannel brethren are more like sport shirts than dress shirts.
Screw up the undershirt. Just because it’s a casual look doesn’t mean you should skip the undershirt altogether. Undershirts are useful whether it’s cold (it’s the perfect extra layer) or it’s warm (your defense against sweat touching your shirt directly).
But don’t make the rookie mistake lots of guys make when they wear an undershirt and no tie. Make sure the undershirt is a V-neck or it’ll show a little triangle of white below your neck and look like a poor man’s ascot.
STYLE TIP: Pairing couldn’t be simpler. Match one of the colors in your shirt to your pants and you’re done. If that doesn’t work, go with the failsafe casual pants, dark blue jeans, that go with everything. As the weather gets warmer, you can relax the look by rolling up the sleeves.