Style Do’s and Don’ts: 10 Ways to Personalize Your Style

Shirts, pants, and shoes. Unless you’re looking to add a blazer, a guy’s daily ensemble is pretty basic. While your female counterparts can easily sport a flashy pair of heels or style a dress over a pair of pants to stand out amongst their sartorial competitors, individualizing a look isn’t so easy for men. So how do you do it? With advice from three real-world, fashion-forward guys, consider this problem officially solved. Read on for 10 ways to individualize your personal style.

1. Embrace your roots

Stylish man wearing a leather jacket

What feels natural to you? | iStock.com

You can take the boy out of the country, but you can’t take the country out of the boy. Cliché? Totally, but it’s also valid. Whether you spent your youth trotting around the globe or in a cul-de-sac clad neighborhood, your past does make you the person you are today. So why not add touches of your upbringing to your personal style?

“I’d like to consider myself a dandy,” said Michael Walsh, a compliance officer at an international bank. “My style has roots from growing up in Westchester [County in New York], where everyone fashionable wore brands such as J. Crew and Ralph Lauren. I still like these brands and shop there.” Southwestern natives can pay homage to their hometown with a tribal printed shirt, while California boys can channel their laid-back roots with a white tee, leather jacket, and pair of light-washed jeans.

2. Experiment with color

Male tailor by shirts hanging from wall

There’s nothing wrong with adding a pop of color to your wardrobe. | iStock.com

When you open up your closet, do you see a never-ending row of ho-hum neutrals like black, grey, and brown? So do most modern men. Sporting dark hues is an effortless way to create a chic ensemble; however, don’t be afraid to integrate zesty pigments into your outfits. “I like bright colors — it’s a direct reflection of my personality,” Max von Weisberg, a traffic marketing manager at Amazon, admitted, “[My shirts, for example] either totally clash with the rest of my outfit or match the whole color palette.” If you’re not ready to clash vibrant colors in one ensemble, start by wearing a colorful shirt with an otherwise neutral ensemble. A red shirt with a pair of charcoal pants is a great example. Looking to up the sartorial ante instead? Opt for a top or pair of shorts in a punchy print.

3. Dress for the occasion

friends drinking beer together

Know when to tone it down. | iStock.com

When it comes to individualizing your style, half the battle is understanding your audience and atmosphere. We’re not giving you permission to change your whole aesthetic just to appease your friends (what is this, Grease?), but carefully choose pieces from your wardrobe based on the event you’re attending. “If I’m out and about, I’ll wear a piece from a more high-end brand such as Givenchy or Balmain,” Craig Altman, an event coordinator at the non-profit Little Kids Rock, explained. “If I’m going to a barbecue, I’ll tone it down with a dress shirt.” Your significant other may not understand why you wore that patchwork blazer to a baseball game, but they would admire a crisp polo and a pair of masculine loafers.

4. Invest in a tailored suit

man wearing a tailored suit

A tailored suit will never go out of style. | iStock.com

As menswear legends Don Draper and James Bond would agree, a tailored suit is a man’s (not-so) secret weapon. “I think the most important purchase for any guy who wants to upgrade his wardrobe to start dressing like a gentleman is a well-tailored suit,” Walsh noted. “Wearing a suit that’s too big on you makes it look like you borrowed you dad’s suit.” With a number of affordable suits on the market, finding one that fits your budget and body isn’t as daunting as you would think. Is there a suit you love, but could use a few alterations? Invest in a tailor or check our easy hacks for faking the perfect fit.

5. Avoid ubiquitous stores

Man and woman shopping together

Shop somewhere that mirrors your style. | iStock.com

Sure, shopping at those big chain stores is the perfect way to score several, stylish threads in one swoop. But if you’re looking to individualize your style, stay far away. Not only will many men have the same pieces as you, but you may find yourself accidentally twinning with a colleague, friend, or family member. “I was interning one summer and took the elevator with a dude who was wearing the same red and blue gingham shirt I was wearing,” von Weisberg said. “Then five years later, I ended up at a bar in Austin and ran into another guy wearing the same shirt. Enough said.” Unless you’re planning on designing your own bespoke fashion line, there is no way to prevent this. However, you can minimize the frequency by visiting more obscure specialty shops or even a nearby vintage store.

6. Don’t be a trend zombie

a trendy man wearing a button up shirt and sunglasses

If you only shop for trendy clothing your clothes will quickly go out of style. | Pablo Cuadra/Getty Images

Ever since you can remember, your parents have been protesting against peer pressure. “If all your friends were to jump off a bridge, would you?” they would ask every time you did something slightly deviant. Consider trends a less morbid equivalent. If the top menswear designers pushed lacey tops down the runway, as some did for the recent Spring 2016 shows, would you wear them? Invest in a trend if you like it, but make sure that it adheres to your personal style. “I think the most important thing about following trends is that you want to interpret the trend so it goes with your personal style,” Walsh suggested. “Something that looks great on someone else might not look good on you because it’s not your style.” You may like the recent stripe trend, but a printed dress shirt would match your taste more than a pair of outré pants.

7. Use your surroundings as inspiration

subway station

Your commute can provide fashion inspiration. | Spencer Platt/Getty Images

If you’ve ever watched an interview with a designer, you would know that they usually never reference style blogs as a source of inspiration. Instead, they credit nature, a film, or historical period. Why not take a page out of an industry insider’s book and do the same? If using nature as a personal style inspiration sounds too ambiguous, we don’t blame you. Instead, grab ideas from your surroundings. “I don’t flip through magazines, read fashion blogs or shop just to comb through rolling racks,” said von Weisberg. “But I do ride the subway every day to work. Open your eyes and reflect on what you like.” From that colorfully-dressed baristo at your corner coffee shop to the cast of Empire, sartorial muses are all around.

8. Never underestimate the power of accessories

a man wearing a watch

Accessories can instantly make any outfit better. | iStock.com

As a kid, you were taught that you’re never fully dressed without a smile. Now, you’re aware that you’re never fully dressed without accessories, right? “I truly believe that accessorizing is the key to an outfit,” Altman noted, “A few extras will tie the look together.” In most countries, guys are socially restricted to wearing a shirt and pair of pants. But the options for upping your accessory game are virtually endless. “I always wear a watch because I think it adds a level of sophistication,” said Altman. “I also try to include a statement belt because of where it lies on your body and the exposure it has to your outfit.”

Distinguishing your ensemble from your fellow men can be as easy as tossing those boring brogues and selecting an expressive moto boot instead. Or add some spice to your regular work outfit by picking up a loud tie or thick-rimmed glasses. Ready to go the whole nine yards? Unleash your inner style trailblazer by incorporating a zesty hat or punchy pocket square into your ensemble.

9. Invest in quality items

Know when to invest

Know when to invest and what to invest in. | iStock.com

Perhaps a family-sized pack of tissues from your local wholesale store may be the only exception, but we find ourselves admitting that quality is better than quantity in every other facet of our lives: friends, tasks at work, and especially clothes. “I would rather invest in fewer, but high-quality items,” said von Weisberg, “A lot of the brands I wear have a heritage, a story that resonates with me.”

You may be able to purchase two sweaters at an inexpensive store for the same price as one luxe blazer, but (if you can) it’s worth spending a few more dollars on a piece. Quality varies from brand to brand; however, pricier pieces tend to be made with extra TLC that will enable your threads to last for many years to come.

And let’s not forget that quality pieces tend to have fun details that are sure to land you on your local best dressed list. “Once someone compliments me on a sharp suit or blazer, I love opening up the jacket and blowing their minds with the crazy linings,” Walsh added.

10. Don’t take yourself (or your style) too seriously

a stylish man wearing a black shirt and sunglasses

Never take yourself too seriously. | Pablo Cuadra/Getty Images

Remember, fashionistos: Dressing up is fun. While it’s great to get compliments, even your sartorially-challenged cohorts will know when you’re trying too hard. “No one wants to grab beer with someone who dresses like a character from The Matrix,” von Weisberg pointed out. On the contrary, people will want to know the guy who enjoys experimenting with his attire and is dressing for himself. Do yourself a favor and make your style a hobby versus a chore.

Follow Kelsey on Twitter @KMulvs

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