16 Style Mistakes Killing Your Look

Style mistakes are common. At one point or another, we've all worn an outfit that caused us to later ask ourselves "What was I thinking?" or "Egads! That's awful! I spent my money on that?" Style, like art, is subjective. What we think looks good could look absolutely atrocious to someone else, and vice versa.

Just like with art, small style details are sometimes difficult to notice until you know what to look for. Details like an understanding of colour theory, what media the artist used, and the science behind what we deem pleasing to our eyes.

In this article we review 16 style mistakes you may be making without realizing it. We break down what they are and how to fix them. Like most advice, feel free to take it with a grain of salt. On with the list:

Wearing Clothes That Do Not Fit Is A Big Style Mistake

Even if that 75% off deal is tempting, don't give in unless the item is available in your size. It doesn't matter if it's a high end brand or not; if it doesn't fit well, it's not worth getting. Even if you get it tailored, it may cost you more than the original retail price to make it look proportional.

Tailors can work their magic, but even they have limits. If you are slicing a few inches off the sleeves, shoulders, and bottom hem, the pattern may become skewed, cuffs may become nonexistent, and the buttons may not be even down the shirt.

Properly fitting clothes will complement your body shape. A piece of clothing taken to a tailor for fine-tuning will look a thousand times better than something baggy or overly tight.

Next time you visit a menswear store, ask one of the sales associates to measure you. Armed with a body measuring tape, they will give you the exact measurements of your arm length, neck, shoulders, and chest so you can find clothes that fit you properly.

You can also use those measurements if you plan on purchasing clothes online. Most online retailers have size guides.

Matching Your Tie And Pocket Square Is A Style Sin

The matching tie and pocket square box sets usually seen around Christmas and graduation may seem like a no-brainer, but anyone with sartorial experience will tell you that wearing matching accessories makes you look like you have no clue how to dress.

Instead of matching, you want your tie and pocket square to complement each other and your overall outfit. If either your tie or pocket square has a pattern on it, pick one of the less dominant colours (typically the second or third most prominent colour) and make that the primary colour in your other accessory.

You can take this one step further and match an accent colour from another part of your wardrobe, like the stripes on your sport coat or shirt, to your tie or pocket square. 

If you decide to wear a single-colour tie or pocket square, have that colour be present, but not as the dominant hue, in your other accessory. You can create a monochromatic look or have your accessories contrast; the choice is yours. As long as they don't stick out like a sore thumb, you're fine.

If you want to learn more about pocket squares, our article A Simple Guide On How To Wear Pocket Squares is full of helpful advice, tips, and ideas.

Not sure what the difference is between a pocket square and a handkerchief? Check out our article What's The Difference Between A Pocket Square And A Handkerchief where we explain the differences in detail.

Wearing Large Logos Can Kill Your Style

Some people view large logos as a status symbol; you aren't popular or rich unless your entire outfit is embroidered with Louis Vuitton or Gucci logos. These people pride themselves in showing off that they can afford these brands, but whether the pieces are authentic or counterfeit is another story. 

Unless you're getting paid by these companies to walk around promoting their brand, there is no reason to be a human billboard. You can still wear branded clothing, but be aware that smaller logos are considered more stylish than massive canvases.

Brands like Polo and Lacoste take a different approach to their branding. Instead of having large logos on their clothes, they opt for smaller ones, typically just on one side of the garment. Despite using more understated logos to adorn their clothing, their branding is still instantly recognizable.

Wearing Shirts With Slogans Is Not Very Stylish

We've all seen them. The tacky t-shirts with witty remarks, grating mantras, or silly slogans. These styles of shirts have become a fad over the years, with many brands hopping on the trend train and creating shirts like "your routine is my warmup" and "this guy runs on [insert brand of beer here]," trying to create brand awareness and loyalty.

These can garner a laugh or two but they get old quickly, especially if they're based around a current pop culture reference or political candidate. The messaging may be funny to a specific demographic, but they look juvenile to anyone who doesn't understand the reference or the humour. Some shirts, especially those with a political message, can be divisive.

Instead, equip yourself with your own snarky or light-hearted take on a current event, joke, or story. The statement or remark will land much better when you add your own emotion to it. Plus, people will think you're witty and thought of it yourself, even if you stole it from social media.

Bedazzled Jeans Or Shirts Isn't Fashionable Anymore

A symbol of early millennium fashion, gemstones caressed the butts, legs, and shirts of many celebrities and musicians. Now, it's mostly associated with older crowds trying to relive their youth. Some fashion brands have tried, unsuccessfully, to revive this trend, but most people view it as a symbol of its time that should not be resurrected.

It has also become the go-to style for the older demographics involved with the modern mainstream rock and urban cowboy rodeo/country scenes. They can be easily spotted at these events because the rest of the crowd is either dressed in modern fashion or in event-appropriate attire (like band t-shirts or real cowboy attire, respectively) while these people sport jewels on their hineys. If you don't want to appear dated or tacky, however, you may wish to avoid this look.

Ripped Jeans Can Be Stylish, If Done Right

Ripped jeans fluctuate in and out of fashion every few years. Typically marketed towards youths, ripped jeans are a sign of rebellion and the counter-culture movement of punks alike. If that is your aesthetic, then by all means rock the crap out of them. When paired properly with a leather jacket and t-shirt, it can be a great rock n' roll rebel look.

For others, ripped jeans can look trashy. Torn clothing may suggest that you don't care enough about your appearance to buy a new pair of jeans without rips. If you work in a professional environment, ripped jeans should never be worn. Instead, wear a pair of dark-wash denim, chinos, or dress pants.

Jeans have been around for over a century, while ripped jeans have only been around since the 1970s. Wearing ripped jeans on the wrong day may make you look like you're too late for the fashion trend, or too early for the next wave of ripped jeans.

Wearing Hats Indoors Is A Style No-No

This is an old-timey etiquette rule that dates back to wartime when US troops were required to remove their hats as soon as they stepped into any establishment or home. Hats were mainly used to keep water and debris out of your hair and sunlight out of your eyes. By removing them, you were less likely to track dirt inside and onto your table if you were seated for dinner.

Wearing large hats, like sun hats, cowboy hats, and pretty much anything with a brim, could be rude in a theatre, concert, or church where you may disrupt the viewing pleasure of the people behind you (they didn't pay to look at the back of your hat).

If you plan to be inside for just a moment, like to pay for gas or deposit some money at an ATM inside a bank, then that's fine. For other occasions, please remove it indoors.

For more information and general rules of thumb for hat etiquette, read our helpful guide titled: Hat Etiquette: When And Where To Wear Your Hat.

Wearing Sunglasses Indoors Looks Silly

Sunglasses are another debate. Some say that wearing sunglasses indoors is perfectly fine, and we agree with them to an extent. If you are photophobic (your eyes are more sensitive to light than most), have a vision impairment, or are hiding a bruise or disfigurement, wearing shades indoors is justified.

You may need to explain yourself to others or come up with a really awesome story of how you saved orphans from a burning building and got a black eye in the process.

Eyes are the window to the soul. When you are communicating with someone, you want to see their eyes and know they're paying attention to you. The same goes for others when they're speaking. If you are wearing sunglasses, they may think you're avoiding them or trying to hide something. Keeping your sunglasses on indoors can be a sign of disrespect to those around you.

Wearing Pajamas In Public Is Anti-Stylish

If you have spent any time in a Wal-Mart, you have probably noticed the abundance of people shopping in their pyjamas (there is even a book on this). The comfortwear trend from earlier strikes again. They could be out just to grab something from the local convenience store or they could be toting around a full cart of groceries. Either way, they are in their sleepwear.

Pyjamas are designed to be very comfortable. The soft material against your skin and the loose fit can tempt even the strongest of strong-willed people to just cozy up on their couch all day and watch their favourite movie. No matter how comfy they are, they shouldn't go outside your front door.

Wearing pyjamas in public should be a no-no for anyone with even a sliver of modesty. Throwing on a pair of dark-wash jeans, a t-shirt, and some Vans or sneakers should be the default "I'm not dressed well, but I need to go out and get something right away" look. At least with this outfit, you've got pockets!

Sandals Or Flip-Flops (Unless You're At The Beach Or Pool) 

Open-toed shoes can be incredibly comfortable, especially during those warmer months. Avoiding sweaty, uncomfortable socks can be a necessity for some. What better way to alleviate the issue than wearing something that allows your feet to breathe. Sandals are a great option, and so are flip-flops.

There is a caveat: open-toed shoes like sandals and flip-flops aren't as stylish as other western styles of footwear. That puts these shoes at the opposite end of the style spectrum from loafers and oxfords. This is only emphasized by the fact that most men don't take care of their feet. Unsightly toenails, cracks, and stinky feet are all culprits.

If you want to experience the warm weather in style, consider investing in a pair of boat shoes, driving shoes, loafers made with a loose weave fabric, or espadrilles. A pair of white canvas sneakers is also acceptable, but be aware they will get dirty fast.

White Socks (Outside Of Physical Activities) Is A Very Big Style Killer

White socks do have a place in every wardrobe, but they should be reserved for the gym or outdoor activities like running or biking. Wearing white socks with your daily outfit, or with sandals (more on that next), can signal immediately to others that you don't know, or care, how to dress.

Even if they're the most expensive white socks made from luxurious materials, they will still clash with nearly everything in your wardrobe.

Invest in some black socks to wear outside of the gym and reserve your white socks for use with your running or training shoes. If you want to show off your fun side, patterned socks can also be worn in informal occasions. Ankle and no-show socks are great in the summer with loafers or sneakers if you don't want to go barefoot.

White socks aren't all bad, though. The benefits of wearing white socks during physical activity include more breathability and moisture wicking abilities that will keep your feet from getting sweaty and stinky. Potential downsides include staining as well as specific washing instructions like only washing in hot water or avoiding fabric softeners.

Wearing Socks And Sandals Is Stylish If You Don't Know What Style Is

One of the seemingly most obvious fashion faux pas, socks and sandals have become a hot-button topic in the world of style in recent years. Ask anyone and they'll likely have strong opinion on socks worn with sandals.

Typically associated with people who don't understand style, post-Covid youth fashion, and celebrities trying to be relevant, socks and sandals seem to be making a comeback, albeit with lots of resistance. It isn't uncommon to see someone trying to pull off the look in the wild.

Some may say that socks and sandals are comfortable since their bare feet are protected from a sudden drop in temperature. Others like the added protection from the elements to avoid foot injuries should a sharp object or branch lay in their path. And, for others, they just like to be different and carve their own path.

Socks and sandals come up time and time again on worst style lists. It comes up multiple times in this Men's Journal article. If you're unsure if your attire looks decent, ask someone for an honest opinion.

Running Shoes Or Trainers As Your Daily Shoes Kills Your Look

Shoes are one of the most important pieces in any wardrobe. They're the only piece that should be in frequent contact with the ground (unless you walk on your elbows). That means they need to offer proper support, fit well, and keep your feet protected from the elements.

A good pair of running shoes or trainers fit the criteria, but they shouldn't be the shoes you grab when heading out to run to the store to get milk.

Most quality running shoes will run upwards of hundreds of dollars, which makes people say "I spent good money on them, so I'll wear them whenever I want!" And sure, you can, but they will wear out much faster.

Similarly to vehicles, the more mileage you put on a pair of shoes, the faster they break down. The foam support, cushioning, heels, soles, and upper can wear out with extended use.

Athletic shoes are constructed in such a way to help you and your body during physical activity. They're created with rigorous, high-impact motion in mind, not leisurely pushing around a shopping cart on a Saturday morning or going out on a date.

Instead, opt for a pair of sneakers or casual skate shoes like Vans for errands like groceries or mowing the lawn if you don't feel like dressing up.

You Can Also Ruin Your Style By Applying Too Much Fragrance 

We all want to smell good. Wearing a fragrance is a non-visual indicator that you are mindful about your hygiene. Overdoing your fragrance can give the opposite effect and others may think you just doused yourself in cologne instead of showering this morning.

If you're unsure about your hygiene, check out our Ultimate Men's Hygiene Checklist.

Depending on the concentration of your fragrance (eau fraîche, eau de toilette, parfum, etc.) and the amount you spray, it may project more than you expect. The higher the concentration of fragrance, the longer it will last.

Our article: A Simple Guide On How To Make Your Fragrances Last Longer will teach you a few different tricks you can use to make your fragrance last all day long.

Some people think that by spraying more of a less concentrated scent on their skin will make the scent last longer; instead, it just makes the fragrance project more. The wearer may also assume that the scent has dissipated after a few hours and apply more, when they've really just gone nose-blind to the scent.

One to three sprays on your neck or behind your ears with a quality fragrance is usually enough. It'll last most, if not all day, and won't cause those around you to experience headaches or light-headedness.

Wearing Big, Chunky, Oversized Wristwatches Can Decrease Your Style

In the world of accessories, men don't have as many options as women. An enduring staple accessory in men's style is the wristwatch. As both functional and stylish statement pieces, wristwatches have been worn for over a century.

Wristwatches come in all shapes, sizes, colours, designs, and with numerous features like chronographs, moon phases, and calendars. Over the past decade or so (from the time this article was published), large watches were "in". Watches 44mm in diameter and over were common. Brands like U-Boat, Diesel, and Fossil were pumping out watches as big as dinner plates.

Like most fashion trends, they come and go. If you look back at the history of watches, they have typically remained on the smaller size between 36mm and 42mm for men and smaller for women. Purchasing a watch within those measurements means that it will always be in style, no matter what the trends are. If you're not sure where to start with watches, our article How Many Watches Does A Modern Gentleman Need explains in detail.

If you prefer smaller watches over larger ones, consider vintage watches instead. Not only do vintage watches tell a story, they can be a great conversation pieces. What You Need To Know Before Buying Your First Vintage Watch is an article we wrote that will help you along your vintage watch journey. Read it while you research vintage timepieces, it will save you a lot of time and money.

Wearing Too Many Accessories At The Same Time Isn't Stylish At All

Similar to spices in a recipe, accessories are best when they're used in moderation. Adding too many gold necklaces or rings to your outfit is like adding too much salt to a meal. You don't want people looking at you and think you're trying too hard or have no idea what you're doing.

The goal of your outfit is to look presentable and well dressed with intention, not like a mannequin from a cheap jewelry store.

The rule of thumb when it comes to accessories is to keep it to a minimum. An exception can be made if the accessory holds meaning like a wedding ring or an heirloom piece from your grandfather. Here are some baselines to follow if you wish to mix and match your accessories:

• One or two rings per hand (if you are wearing multiple rings, space them out at least one finger apart).

• Only one watch on your wrist.

• One or two bracelets on your other wrist (not on the same one as your watch; you could risk damaging the case and it looks imbalanced).

• One necklace or chain.

Avoid accessories that are 'iced out' or overly blingy. Wearing accessories that beg for attention isn't the best way to get attention. You could be inviting the wrong attention that could lead to getting into an altercation and possibly losing your expensive, shiny jewelry. 

Instead, stick to modest and understated. True connoisseurs will appreciate the subtlety and class.

Summary

Style rules are meant to be broken, but only if you know why the rule was made in the first place. Breaking any of the style rules mentioned above won't have the fashion police knocking on your door (except for maybe the socks and sandals one) but a sartorial-minded person understands that boundaries can be pushed a bit, within reason.

Being mindful of style mistakes can save you from dressing inappropriately. Keep these tips in mind next time you put an outfit together.

Now that you know what to avoid, read our article on How To Update Your Wardrobe In 10 Easy Steps and become motivated to dress well by reading The Power Of A Sharply Dressed Gentleman

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