You start your morning with a quick peek at your iCal: A working breakfast with the boss, a major client presentation, and – oh, right
– that special date with that sexy someone you've been looking forward to all week. Now cut to you staring blankly at your closet: How in the world am I supposed to be dressing day to night? You're already ahead of the game just by asking the question. You see, they had one thing right in the Boy Scouts: Be Prepared. Just by planning ahead you can avoid any sartorial snafus that might arise when your schedule throws you a curve ball. It's called transitional dressing, and it will make your life simpler and more stylish all at once. You don't want to be the stuffy guy in a suit and tie at the sports bar while your buddies are comfortably shooting pool in jeans and artfully loosened-up dress shirts. Alternatively, you never want to be the dude sporting a "casual Friday" outfit of an ill-fitting polo shirt and khakis – any day of the week. Let's start with your work-to-evening ensemble then move into upping your sartorial game with accessories, shall we?
THE LAYERED LOOK
The key to office-to-evening dressing? Layers. As you're getting dressed, think of each article of clothing as a stand-alone piece, from a slim-cut T-shirt under a fitted dress shirt with a slick blazer or suit jacket on top. You can then shed those layers as your workday turns into night. Trousers, chinos, or dark-wash jeans can all be work appropriate, depending on your office culture. "A great way to take a men's outfit from work to cocktail hour is to stick to business-casual clothing," says Katie Schuppler, owner and personal style consultant of Chicago-based KS Style Consulting. "Opt for a button-down that looks dressier when a blazer is added over it, or wear a blazer for the work day and then take it off at night." "Another tip to make the transition from day to night a little easier is by rolling up the cuffs of the button-down shirt a bit for a cooler and trendier look," Schuppler continues. (Ever wonder how to get the perfect rolled cuff? Check out this awesome sleeve-rolling
master class from menswear blogger Style Girlfriend
. These things matter, guys!) Now, we know not all of you work in business-casual environments, but these simple tricks can work with traditional suits, too. Just leave your suit jacket and tie at your desk for the day. It's also helpful to think of your suits as two separate pieces for added flexibility. Wearing the jacket with jeans works for a casual office afternoon followed by an evening drinks date, and pairing the pants with a dress shirt and sweater jacket takes you from a day of business travel to dinner at your favorite neighborhood trattoria.
THE LITTLE THINGS THAT COUNT
Accessories can make all the difference in effortlessly ushering a look from morning to night. Steal a tip from the ladies: Keep an extra pair or two of shoes at the office. You know how your female counterparts slip into heels or flats depending on their day and where they're headed after work? You too can make this Clark Kent-to-Superman style transition just by swapping out your serious footwear for cool boots or stylish sneakers. As Schuppler explains: "Throw on a semi-casual pair of shoes instead of keeping on your work shoes to switch up your whole look." Make like Mr. Rogers and slip into something more comfortable. Not only does it change your outfit, it might even elevate your mood, taking it from the daily grind to that magic evening glow. Guys, it's truly as easy as that. If you really want to take your after-5 look to the next level, consider your (understated, masculine) bling. Adding a few leather wraps or metal bracelets to the same wrist as your watch injects some fashion-forward flair to your off-duty ensemble, just like cool aviator shades ensure all eyes are on you. And, whatever you do, stash your briefcase at coat check. No one wants to hang with that