9 Tips: How a Guy Can “Up His Game” in Style

Let’s face it, it’s not easy for a guy to be stylish. Women have a lot more options – everything from different types of outfits to accessories to hair styles.

Yet, for guys, that doesn’t mean that it’s an all or nothing thing. It’s not a choice between a three-piece Armani suit and – gasp! – cargo shorts. There are a lot of options in between being totally dressed up and dressed down. Except cargo shorts. Those are no longer an option.  Just don’t.

We reached out to stylists and fashion experts to give some advice on how a guy can “up his game” in style and fashion. Here are the top 9 tips:

Tip #1: Size Doesn’t Matter. But Fit Does!

Without question, this was the most popular response: get a tailor, get a tailor, get a tailor. After all, style is not about fitting in your clothes, it’s about making your clothes fit you.

“Excess fabric is the death of style,” said Tavia Sharp a personal stylist and men’s fashion expert with her company Styled Sharp. “You can definitely spend money on higher quality, stylish clothing but if the fit is off it's still not going to look good on you. Proper fit is key! You can actually spend less money and look like a million bucks if you buy clothes that fit properly.”

Tip #2: Know Your Head

Getting clothes to fit right is important, but another area often overlooked by many guys is their head. Specifically, making sure that their hat is a good fit. Yet, getting it right isn’t too difficult.

“To measure your head, take a flexible measuring tape and measure the circumference of your head where your hat will sit, usually just above your eyebrows and above your ears,” advises Mike from Lamood Big Hats. “Keep the measuring tape level and firm. Measure from the back of your head bringing the ends together at the center of your forehead right above your eyebrows.  A baseball cap is too small if it sits above an inch over the ears or, if it’s an adjustable cap, if the hat forms a ‘V’ on the last snap.”

Tip #3: Cut Out the Black

Let’s be honest, black is the easiest color. It looks good on everything and everyone because it’s a foundational look. But to be stylish, you should look for more.

“A quick way to up your style game is to cut the color black out of your wardrobe,” said personal stylist Vanessa Valiente. “If you have the resources, embrace a lighter color palette entirely. Skip black, charcoal and midnight navy and create a capsule collection of khakis, light blue, light grey, lavender, sage green, and a brighter blue to replace your navy. With this palette you only need two shoe and belt pairings: tan and that brighter navy. This seems somewhat daring at first, but it's just a color change. Your silhouette and choice of garments will stay the same.”

Tip #4: Get Dope Socks

Style is not only about getting the “big” things right, such as killing cargo shorts, but also paying attention to the small details that can really finish off a look. In fact, it’s often the final element that can make you stand out.   

"Socks give the most bang for the buck regarding style and are one place a guy should have fun with his wardrobe,” said Brice Pattison, Fashion Director of The Black Tux. “Whether you're wearing a tuxedo or broken-in Levi's, socks are an easy way to step up any look. If I can advocate for one way to invest more it would be switch to fine merino socks. They're soft, durable, lightweight, sophisticated, breathable, antimicrobial and the list goes on. Pantherella is my go-to, and they don't disappoint." 

Tip #5: Square the Pocket

Another minor detail that makes a big impact is a simple piece of cloth – both in terms of looks but also saving you from throwing out an old outfit.

"A well-matched pocket square can save an outfit," said Dr. John Mayer of Mister Burlap. "I can have on one of my jackets that was a step away from ending up in the charity bag, but I splash in a good pocket square and the tired jacket gets compliments all day! Pick a square to 'pop' some color in your outfit and make sure it's not something that looks like grandpa's pajamas stuffed in your jacket, like traditional squares."

Tip #6: Get a Watch (Duh)

This tip is so self-promotional, it’s ridiculous. But yes, as America’s next great watch company, we are naturally biased and think every guy should have a good mechanical watch. In previous posts, we’ve offered tips on how to buy a watch for someone else and we’ve broken down the top most confusing words of the watch world to help you understand the important things in buying a watch. However, as our watches are in a pre-launch phase, it is not all about us.  Buy any watch, it doesn’t have to be ours.

Whenever I’ve bought a watch, as cheesy as it sounds, it’s because it “spoke to me” in terms of style. I knew immediately once I saw it that it was the watch I wanted. If a watch doesn’t grab you right away, move on until one does. But as we say in one of our themes on Instagram: the watch completes the look. So, make sure your look is complete.

Tip #7: Mimic a Role Rodel

What if you need bigger ideas than the small things? What if you need some inspiration on how to put an entire look together? Or, what do you do if you don’t your own “look?”

"Look at others to find your own style," said Geoff Odoi. "Whether you like to dress street, professional or comfortable, to find ideas for your style, find a role model or brand that matches you best.  You can use them as inspiration to then make sure your own personality comes through. For me, I find checking weekly on websites like GQ help me keep up with the latest. And then, instead of spending a fortune on the clothes those models are wearing, I go to lower cost stores like H&M and thrifting to match the look I think expresses who I am best."

Tip #8: Suit Up

At the same time, sometimes there’s nothing as stylish as a classic suit.

“The day you make a sale is the day you earn your money and the day to suit up,” said Joseph Rosenfeld, a Personal Brand & Style Strategist based in New York and Silicon Valley. “A dark suit that complements your build and height, a white shirt that matches your teeth, and a tie that matches your eyes is always a winning combination. Even if it sounds like a uniform, the customized color selections get onlookers focused on you and your message.”

Tip #9: Grooming Isn’t Manscaping

Finally, after you’ve put all this effort into making sure the look is right, the last thing you want to do is have a distraction that spoils it all.

“Pay attention to the subtle details,” said Fred Connors, a stylist whose salon FRED. is located New York’s Lower East Side. “Good grooming isn’t just brushing your teeth and the occasional pomade. Unnecessary hair has to go and is often distracting. I am not talking manscaping your lower region but rather the hair people see every day. Nose hair, ear hair, crazy eyebrows and neck hair should be trimmed at all times. Purchase rechargeable trimmers at your local CVS and they will do the trick.”

For a special bonus tip, Fred advises: “Lastly, make sure you smell good. If you don’t have a clue about fragrance, visit the nearest department store and get some help.”

What do you think? Are there other tips you can offer? Let’s keep the conversation going in the comments on Twitter or on Instagram.