Written and Produced By James Vincent

It can be tough enough for a guy to coordinate a wardrobe as an ongoing, organic thing—but even tougher to coordinate a long weekend wardrobe. Let’s say you have to leave from work in a suit, go to the gym etc. before catching a flight to Chicago. You also need to grab a nice bottle of wine for your weekend host and make a quick stop at Madison Vine Wines, located in Chicago’s trendy West Loop neighborhood. A great place for events and so neighborhood in fact, they let you put a pic of your pooch (or kitty) on your favorite bottle of wine.

First of all, you need a suit—a good basic suit—that’s more comfortable for all the running around you have to do on your lunch hour for the last minute stuff before the trip. A good bet this year is this medium navy Ralph Lauren Flex suit that moves with your body. It’s basic – but it is so damn comfortable.

Second—you DON’T want to wear the suit on the plane and you didn’t want to over stuff your bag with another outfit. The weekend is packed full of events—say for a friend’s engagement party—and there was just not room in the bag for one more thing. No sweat—just throw a denim shirt and a vintage vest in your work back pack and after your workout—throw the suit jacket in there, put the suit pants back on with the denim shirt and vest.  Not only will you feel comfortable, you’ll look like you wear this cool, hipster kind of look every day.

A good all-around sport coat can be a guy’s best friend—whether for a trip when you’re not quite sure where you’ll be going—or good wardrobe basics. And by all around—pick one (or two) that can be dressed up or down. This off white textured, unlined jacket looks great for an engagement party or out for dinner paired with dark wash jeans. It would look equally great paired with a dark navy—go for contrast—trouser in a light weight four season wool for a dressier occasion.

Another sport jacket—and another indication that some 70’s era style looks are back in a big way—is this killer plaid number in linen. What a style statement. What a way to make an entrance. Plaid isn’t for everyone, but if that’s you—go for it. This one is somehow muted being in all blue rather than in multi colors. This jacket could definitely be paired with chinos or a pair of linen trousers. And it’s just perfect when styled with a pair of slim white jeans. Any shirt/tie combo will work—this blue knit tie with the blue pinstripe shirt is just the right pairing for any occasion.

Spring is elusive in the Midwest—tantalizing warm and gorgeous for a few days—then, when you’re just about to start replanting your back porch planters—zap—chilly with showers. And since it’s always a drag hauling along an umbrella wherever you go—invest and pack along a hooded parka.  That way, if you’re just out and about on a rainy weekend day and everyone else is fiddling around opening up umbrellas or wandering where they lost theirs, just flip the hood up and you’re good to go. And who says you shouldn’t wear white jeans until Memorial Day? Get a head start with the same white jeans you packed for the plaid sport coat—they’ll look great with this deep navy parka.

So you’ve had your weekend of events and it’s finally time to kick back and relax with a glass of wine and think about packing up again.  Big bonus for the weekend—it got warm all of a sudden on your last day. You thought ahead, as it turns out. You wandered at the time—well, it might get warm enough for these and packed a pair of shorts, a white polo shirt—and, wait, what’s this—a hat too? And, why wouldn’t you?

Photography, Alejandra Guererro; Model, John for Ford Models Chicago; Grooming, Ashley Condron; Styling, James Vincent; Shot on location at Madison Vine Wines, Chicago