Five Menswear Mistakes To Seriously Avoid At All Costs

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When it comes to dressing well, it’s an unavoidable reality that when combining new pieces and trying to find the perfect look, there’s a chance things might not go as planned. Sometimes the bold, daring wardrobe choices that you thought looked amazing in your bedroom mirror result in more friendly ribbing from your pals than the copious compliments you had hoped for.

It can be a little embarrassing in the moment, but little missteps happen to everyone (in hindsight, my brief phase where I wore unzipped hoodies with the hood up literally all the time wasn’t the amazing look I had believed it to be) and one mistake here or there is really nothing to be ashamed of. After all, if you’re not willing to take a few risks and try some new things now and again, you’re not very likely to progress your sense of style beyond where it is today.

However, there are some fashion mishaps so easily avoidable and so widely repeated by menswear newbies that they border on unforgivable.

Thankfully, avoiding these common blunders is generally as simple as recognizing why they’re considered blunders in the first place. By the end of this list, you’ll understand why these menswear mistakes are so notorious and what you can do to avoid making similar ones.

Mistake Number One: Clashing Formality

In this day and age, there is perhaps no article of men’s clothing more synonymous with embarrassment than the fedora. Though often well-intentioned, this particular garment has become synonymous with pubescent attempts to “class up” an outfit by simply adding a single item (in this case, a markedly formal hat) without any regard for how it might interact with the other things a person is wearing. The result is something that evokes insecurity and confusion: definitely not a good look.

This stereotypical usage of a fedora fails because it erroneously assumes that a garment that is more formal is always better, despite the fact that adding a garment like this to an otherwise casual outfit is just as silly as adding a meticulously tailored sport coat to shorts and a tee shirt.

Fortunately, clashing formality like this is just as avoidable as it is embarrassing -- one should always consider how an outfit works as a cohesive whole unit as well as considering individual pieces. As long as you’re thinking about what’s appropriate for the context in which you’ll be wearing your outfit when constructing it, and make sure that all the items in a given outfit can reasonably work together, you’ll have no trouble avoiding making this mistake.

Mistake Number Two: “Frankenstein” Garments

When shopping for new clothes, wanting to maintain a focus on value per dollar spent is perfectly reasonable. However, one way to absolutely decimate the quality of your outfit in the pursuit of value is to purchase strangely mutated items that attempt to accomplish a number of (often competing) goals all at the same time.

No, you cannot purchase a pair of shoes that are simultaneously boots, formal shoes, and daily use sneakers all at the same time, but that doesn’t stop manufacturers from trying to convince you. In this case, it would literally be a better value to simply buy zero pairs of shoes than to attempt to make one of these monstrosities look good.


In my view, it’s always better to make calculated investments in single items that perfectly accomplish their set of goals rather than to try to turn one Frankenstein’s monster of a garment into some type of wardrobe panacea. At the end of the day, you’ll get much more use and satisfaction out of slightly more expensive pieces that are great at what they do than attempted multi-purpose items that bring confusion into any outfit they enter.

Mistake Number Three: Cargo Shorts. Ever.

Just stop it.

Throw them away. I’m serious.

I don’t care why you like them. Unless you are literally on a rock climbing expedition right now and need five discrete bulging side pockets to hold your carabiners and mini compasses, I don’t wanna hear it. They all belong in the trash and that’s all I have to say about them. Moving on.

Mistake Number Four: Obviously Low Quality Imitation Materials

I’m not the kind of purist who’d tell you that wearing pleather or faux suede is always a bad idea -- I’ve owned and loved pleather garments myself in years past -- but especially for those looking to invest time and energy in looking their best, I’d encourage a healthy dose of skepticism when investigating inexpensive materials like these.

Not only do inexpensive materials like these tend to degrade extremely rapidly, limiting the value of the low price tag that may have piqued your interest, but they can also range from looking acceptable to looking downright dire. The wrong piece of pleather -- something that looks plasticy and costumey -- has the potential to ruin the impact of an otherwise well-constructed look.

Fortunately, this error is also pretty easy to avoid: see inexpensive garments in person before buying to get a sense of how the material looks in person and reacts to light, and consider saving up or even buying used as an alternative to a cheaply constructed piece.

Mistake Number Five: Poorly Fitting Clothes

This one is probably one of the most ubiquitous mistakes that men looking to dress well can make, and also one of the fastest and most dramatic ways to improve the way you look in any given outfit.

At the end of the day, no matter how much your outfit cost, what it’s made of, or how deftly you’ve contextualized it within your personal style and the context of the occasion, it will look bad if your clothes don’t fit you properly. Conversely, a perfect fit has the potential to save some of the most questionable fashion choices. It’s not a cure-all, but it absolutely goes a long way to ensure the items that make it into your wardrobe are appropriately sized and look flattering on your body.

If you take away one thing from this article, I hope it’s this: the way a garment fits on your specific body is perhaps the primary factor to look for when shopping for clothes.

As I’ve previously said in a recent article, I think trying a garment on should be a prerequisite for almost any purchase because fit can vary so wildly between brands and labels. However, if you’ve found the perfect item but can’t quite nail the sizing, you still have options: a competent tailor can help nail down the finer details and improve the quality of almost any type of clothes. Thankfully, as with many of the other entries on this list, correcting this mistake doesn’t require a ton of effort or specialized knowledge, and can be very easy to avoid or correct with a little care.

Ultimately, anyone looking to improve their style is bound to make a mistake at least once, but hopefully by reading this article you’ll be able to avoid some particularly egregious errors.

Ready to find the perfect new clothes to fit your next occasion? Hellman Clothiers has got you covered: why not drop by our location in Downtown Cincinnati or visit us online to experience some of the finest American and European luxury menswear brands on offer in the region.