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How to Help Men Dress Casually Without Looking Sloppy

Right or wrong there’s an assumption out there that once a guy finds a woman who will love and marry him, his clothing and style will improve exponentially since she will take over dressing him. As a men’s fashion stylist I’ve made over many a husband, and they almost always tell me the same thing. Having their wife pick out their clothes may have been OK in the beginning of the relationship but later down the line it caused friction. The husband starts to feel like he’s being nagged, even if he knows he could do better. And the wife hates policing what the husband wears, she simply wants to be attracted to him and be proud to show him off in public. That can be especially challenging when the husband is out of his work attire and in casual wear. Work clothes are easier for them to manage because it’s almost a uniform. Plug in dress shirt up top, plug in boring khakis on bottom, etc. Breaking out of that uniform is a whole other topic, so in this post I want to share the key points to putting together killer casual looks. First let’s take a look at why casual wear can be so confusing. 1. Men have many more clothing options than ever before with little or no guidance on what of those increased options will work specifically for them. 2. Most men value comfort above all, and since in their professional lives they put on ‘nicer’ clothes that are not as comfortable as what they wear on the off hours, their assumption is that in order to look better they have to dress fancier and therefore be less comfortable (this bit couldn’t be further from the truth, in fact comfort and style do happily co-exist at the same point in space and time, it’s simply a matter of finding the right brands). 3. As mentioned earlier, there is no formula for casual clothes like there is for business wear, or is there? The result of the above is that on weekends too many guys end up wearing their outdoor gear, workout wear and game day jerseys as casual clothes. Obviously that’s good for hiking, the gym or at a game respectively, but for going out, get-togethers with friends and other social activities, it doesn’t work. What a man puts on his body can be a confidence booster, or killer. Women know this already: when you’re wearing something that you feel absolutely great in, your entire experience of life transforms. You’re more confident, happier, at ease with yourself and others. That’s really why clothing matters, whether you’re at work or at play. So back to that formula.The best part of this is that once a guy understands the basics below it’s no more effort to toss something on that looks great and makes him feel like the king of the jungle, than it does to toss on something sloppy.


Fit is 75% of looking great, without a good fit no matter how expensive or ‘nice’ the piece is, it won’t look good on. Most men buy clothing that is too large.Being men, they think larger is better, so a guy who should be wearing a medium purchases a large or XL, a fatal mistake since the larger size swallows his frame and makes him appear smaller and sloppy. With a good fit the shoulders are the most prominent part of the man’s silhouette and the rest of the garment skims naturally along the body rather than hanging loosely, or pulling and bunching because it’s too tight. The key is to pick each garment based on how flattering the fit is and not by what the tag says.


Every item from a sweatshirt to a blazer is made in a variety of cuts and fabrics to give it a particular feel. Let’s take a look at T-shirts for example. There are the typical Hanes or swag T-shirts that are cut like a box with arms, and then there’s a huge array of trim cut tees. The trimmer cuts have the same width in the shoulders but they taper slightly at the torso, that cut flatters the man’s physique instead of distorting it like the boxy tee. Fabrics and prints also play a big role in distinction. You don’t want bland nor do you want flashy, aim for the middle. For example on one end of the spectrum you have the boring white cotton tee, on the other end, the loud in-your-face print of an Ed Hardy tee. Distinction is about choosing well-cut pieces with subtle design details.In the case of a T-shirt this could be textured slub cotton trim tee in his favorite color.


Layering is where a man gets the bulk of his individuality.Since every guy has a pair of blue jeans, it’s what he wears with those jeans that make him stand apart for the right reasons. Even in weekend wear a top ‘finishing’ piece adds a lot to a look. For example, an unassuming T-shirt and jeans combo looks a thousand times cooler when you add a tailored soft knit zip hoodie.


Men know accessories as black and brown shoes and a reversible belt. While there are a ton of casual accessories for men, we’ll tackle the belt here. The most common mistakes men make in this category are wearing a black business leather belt with jeans, and their gym sneakers as casual shoes. Jeans and shorts need a belt with the same relaxed feel, that means rather than shiny leather opt for a casual belt. This can be fabric like nylon, cotton, or a woven material, or a distressed/washed leather belt. Sneakers are for working out, end of story. Used as a replacement for casual shoes they suck out every ounce of masculinity and make the guy look like a Floridian retiree. Instead, pick up a pair of driving mocs, boat shoes, or street sneakers, which will all look brilliant paired with jeans or shorts and be every bit as comfy to wear. So there you have it, good casual style in four steps. Start with great fitting, distinct pieces, layer them, and add a couple of accessories. I hope this helps the men in your lives sharpen up their casual looks. If you have specific questions you can always email me at For more men’s style advice check out Emmi Sorokin Fashion Crime Fighter


4 Responses

  1. These are great guidelines and information. It’s doesn’t take any more time to put on something casual yet sleek as it does to put on something slumpy. Thanks for educating the masses.

    1.  Thank you, Kimberly.  I’m delighted you found it helpful and you’re right about putting on something casual vs. slumpy — it’s just a matter of making sure that’s all you have in your closet so it’s simple.  Enjoy!

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Ginger Burr is a fashion stylist and personal shopper serving clients worldwide from metro Boston.