It’s always a sad day when you walk into your favorite clothing store and realize that you’ve officially outgrown it. Where did the time go? Why are all the mannequins dressed so young and hip? And why are you suddenly using the word ‘hip?’
Although it can be a tough realization, look at it this way: You now have an opportunity to rebuild your wardrobe with pieces that have real staying power. With the right style combinations, you can create looks that transcend any flash-in-the-pan trends and manage to keep yourself looking sharp at any age.
Need some style inspiration? Here are a few classic looks that will stand the test of time.
1 A Polo Shirt and Khaki Shorts
The trusty polo shirt and khaki shorts combination has long-been considered the quintessential summertime outfit for men of all ages. It doesn’t take a style genius to see the appeal: It’s a lightweight, breathable and casual combo that makes guys look and feel good.
During the warmer months, you’ll see men of all ages, from retiree dads to adorable toddlers and everything in between, rocking a polo shirt and classic khaki shorts. If you want to stand out or just feel like mixing things up, consider wearing a striped polo shirt in lieu of solid colors and pair it with casual shorts for a sporty yet timeless look.
2. A Sport Jacket and a Button-Down Shirt
It’s a basic style fact: A guy’s business casual wardrobe isn’t truly complete until it has at least one sport jacket and a few button-down shirts. This reliable duo is your style secret for—well–everything. From impressing the higher-ups at your 9-5 to dazzling your date later that evening, you simply can’t go wrong wearing a stylish sport jacket and a quality button-down.
To plant yourself firmly in business casual territory, consider pairing this duo with a pair of men’s chino pants and a nice tie or a pocket square.
To plant yourself firmly in business casual territory, consider pairing this duo with a pair of men’s chino pants and a nice tie or a pocket square. If you already own a few solid-color button-downs, expand your selection by picking up a button-down shirt in a unique pattern such as gingham or plaid. The pattern will add a hint of visual interest to your outfit without making it look too busy.
3. A Plaid Button-Down and Dark Wash Denim
So, you’re admittedly not a master of menswear. That’s okay! Who needs to be when you have a plaid button-down shirt and dark wash denim in your clothing rotation?
Plaid and denim are an effortless, no-fuss combo that has been helping average Joes look rugged and masculine for centuries. It’s practical, stylish and a look that is just plain difficult to mess up. Perhaps that’s why so many of us stock up on our favorite flannels before the first leaf of fall even hits the ground.
To keep the look from appearing on the sloppy or grungy side, be sure to pair your plaid button down with a high-quality pair of dark wash denim. Complete the look with a pair of canvas sneakers for the perfect weekend outfit.
4. A Pullover Sweater and Chino Pants
You want to be comfortable at the office without looking like a total slob. What’s the solution? A cozy pullover sweater and chinos, of course.
Men of all ages have been rocking this look for decades for its ideal balance of comfort and style;Your grandfather probably wore this look back in the day with a nice button-down and a tie under his pullover. Depending on your office dress code, you may want to take a tip from his style playbook to boost your professional image.
If you’re worried about sweating too much underneath your pullover, consider wearing a cooling shirt designed with cooling minerals and technology that wicks away sweat to help keep you dry. With a cooling shirt as your base layer, you’ll manage to keep those embarrassing sweat stains at bay while looking supremely professional and stylish.
With a cooling shirt as your base layer, you’ll manage to keep those embarrassing sweat stains at bay while looking supremely professional and stylish.
5. A Shearling Jacket and a Crew Neck Sweater
Maybe you’re lucky and don’t live somewhere cold enough to warrant heavy outerwear and proper layering. But in case you do, the shearling jacket and crew neck sweater combo needs to be on your style radar.
Although shearling jackets have a long and storied history, they’re commonly associated with the 1970s when Robert Redford wore one (with a grey crew neck, might we add) in the film Downhill Racer in 1969. After that, the shearling jacket soared in popularity and cold-dwelling men have been grateful for its fashionable warmth ever since.
6. A Harrington Jacket and a White T-Shirt
The Harrington jacket is a menswear item that you’ve probably seen before, even if you may not have realized it initially. This iconic jacket style has been worn by many famous faces throughout the years, including Steve McQueen, James Dean and—more recently—Daniel Craig and Bradley Cooper.
Invented in the 1930s by a British clothing company called Baracuta, the Harrington has endured a long style reign for obvious reasons: It’s lightweight, comfortable, versatile and waterproof. Simply put, it’s a must-have piece in your closet that pairs perfectly with your favorite t-shirt.
Okay, sure, you could pair the Harrington with virtually anything and still look cool. But the t-shirt and Harrington jacket combo has been proven to stand the test of time by none other than James Dean, who rocked the look in Rebel Without a Cause.
7. A Camel Trench Coat and a Suit
If there is one camel coat you own, let it be a camel trench coat. Classic, clean and vastly underutilized, the trench coat has remained relatively unchanged in design for more than 100 years—a major testament to its enduring appeal.
Although the trench coat can be worn with casual looks, its true sartorial power comes alive when it’s paired with a classy suit. You’ll often see this particular stylish combination in places such as Chicago and New York, both of which have a high population of busy professionals and temperatures which frequently dip below freezing in the winter.
Although the trench coat can be worn with casual looks, its true sartorial power comes alive when it’s paired with a classy suit.
If you want to try this look for yourself, start by incorporating blue into your look (it will pop against the camel color). For instance, pair a solid blue button-down with a gray suit, throw your trench coat on and finish off the look with brown dress shoes for an effortlessly smart and sophisticated outfit.
Styles That Work for Every Age
Styles that work for any age solve a number of style conundrums that have plagued men for decades. For instance, you’ll never look back at photos and cringe when wearing one of the outfits mentioned above and you also won’t need to replace your wardrobe every season after the latest trends are no longer considered in fashion.
Needless to say, classic and timeless looks are the true hallmark of a stylish man. Pick up these looks, add them to your clothing rotation and never look back.