How To Dress Up Your Denim Style | Men's Dapper Jeans Guide

Posted by Rishi Chullani on

Alyssa Breeden

Given the men's wardrobe staple that are denim jeans, knowing how to dress up your denim style is of critical importance. In this men's dapper jeans guide, we cover the types of jeans fit, different styles of washes, and finally, how to style your denim jeans. 

Few fashion pieces have stood the test of time like denim trousers, i.e. blue jeans.  A great pair of jeans can be quite expensive so you want to make sure that you get it right, especially since they usually serve as the base of your whole ensemble. 

Denim is the perfect way to bring a casual, cool look to your professional wardrobe.  With so many choices available how do you choose an appropriate pair that works for you, and not against you?  Color and style are just the beginning.  What about decorative stitching and rear side branding?

 In this post we will not only explain why denim is so versatile, we will also help you narrow down the best fit, color and style for your needs.

Denim Jeans With Sports Coat and Silk Tie

(A flawless use of denim by @stevetillystyle on The Dark Knot’s Instagram)

Leather & Beaded Bracelets from The Dark Knot

When to Wear Denim

When worn properly, denim can give you a polished and professional business casual look with zero effort.  You can successfully dress up while dressing down.  I am pretty sure that is what we all want, right?

Denim translates beautifully into just about any situation – just be mindful of the details.  Jeans can translate any outfit to casual, though when paired with formal accessories like neckties, you can achieve an interesting (some may even say “perfect”) balance.

For example, casual Friday usually ends with a great happy hour, so you should dress to prepare for this.  A great way to plan for the day would be to pair your best formal (dark, well-fitted – more detail later) jeans with a solid, collared polo or a casual dress shirt.  You may also find that mixing cardigans and chunky sweaters translate really well with well-fitted and formal jeans.  To further that look, try layering with a solid shirt and slim necktie.

Please feel free to view The Dark Knot’s range of Skinny Ties.

To view The Dark Knot’s range of Knit Ties, please click here.

Silk Knit Ties

Now let’s look at how to actually choose a great pair of denim for your unique style:

Types of Fit

At the basic level, there are five fits of denim to choose from.  Be sure to look at your body shape, take into account the parts that you want to accentuate and which parts you may want to downplay.  For example, a bottom-heavy build probably wants to avoid any style and cut that accentuates unwanted weight.  On the other hand, pencil-thin builds want to be mindful about not “swimming” in their jeans. 

Pro Tip:  More often than not, slim and straight-leg fits are the go to options for business-casual styles.

Skinny Fit

Skinny, skin tight.  This is a class reserved for those who may be very thin and tend to “swim” in all other fits and boy bands of the early 2000s.  This fit has the most stretch, think jeggings, and should fit snugly all around.  A bold choice for most.

Skinny it Jeans

The Skinny Fit styled by

Slim Fit

This fit, like the skinny fit, is a tighter option.  Most formal jean choices are in the slim category, as they tend to fit like a nice pair of chinos.  Slim-fit jeans should slightly hug the thighs, knees and calves (without bulging) and loosen up around the ankles.  This is a clean and crisp look for any size, which is why this is the most preferred fit for most.  Slim-fit jeans generally have a bit of stretch to hold their shape throughout the day.

Slim Fit Jeans

A great use of slim fit denim by Khoi at

Straight-Leg Fit

The straight-leg fit is a bit more forgiving than the slim fit, making it a great transition style for those of you used to loose denim.  Straight-leg fits are also great for active men who know that they are going to be moving a lot in their clothing but still want to look polished.  This fit is cut at the same angle all of the way down, meaning they are shaped like tubes.  A cut like this means that jeans are going to fit a little tighter in the larger portions of your legs but hang looser in other areas (as opposed to being shaped around certain features like a slim fit would be).  It is advisable to look for a little stretch in your straight-leg fit to ensure optimal comfort.

Straight-Leg Fit Jeans

Impeccable straight-leg fit by

Classic Fit

Classic fit denim is loose throughout, making it a roomier option for those who can not stand anything tight.  However, with the classic fit you loose shape and can easily slip into a sloppy appearance.  A loose fit can also mean that you are leaning into flare or bell-bottom effect.  Be very mindful about the break and cuff (see below) of your classic fit denim.

Classic Fit Jeans

A perfectly tailored Classic fit by Joe’s Jeans

Relaxed Fit

The relaxed fit is the roomiest option, mainly reserved for those who prefer baggy street styles.  To really pull off this cut you have to fully understand balance and proportion.  When done properly, it is possible to use the fuller legs and seat of this fit to your advantage.

Relaxed Fit Jeans

Great uses of relaxed denim and proportions by D’Marge

Types of Washes

At a basic level when the word “wash” is used in regards to denim, people are generally speaking of the color.  In terms of color, there are two main options:  blue and black.  However, the way that those colors are treated to create the final product is ultimately what the “wash” is referring to.  For our purposes we will explain in “blues”.

Types of washes for jeans

Washes currently available at

Classic Wash

A classic wash is a casual denim preference.  This is going to be where medium-blue jeans fall.  To achieve this look denim makers take a darker shade and lighten it with bleach and lightening agents.  The classic wash pairs best with a t-shirt and a BBQ sandwich.

Vintage Wash

This wash is pre-distressed, giving you a worn-in look right out of the store.  This denim will look a bit faded and generally has had light sanding around the knees and seams.  The vintage wash is a great choice for rugged types as it pairs beautifully with worn-in flannel.

Dark Rinse

Dark rinse denim is the most versatile, as well as the most formal of the washes. This wash is the darkest, inky blue (usually with some shading for shape enhancement) and pairs well with every collared shirt in your closet.  We highly recommend keeping a pair of dark rinse denim on hand for business-casual situations. 

Raw Denim

This wash is exactly what it implies, raw.  Raw denim has been unwashed, untreated and it is often quite rough to the touch.  However, raw denim can be shaped to your contours by simply wearing your jeans wet for their first wash (seriously, Google it).  This process not only shapes your denim but also softens it.  Depending on the cut of your raw denim it can be quite versatile in your wardrobe.  Plus, it will fit like it was made for you.

The Small Details Can Speak Volumes

Now that you have a wash and fit in mind you can effectively narrow your search to a few great options.  Here’s where the small details come into play, and here is what they mean to you:

The Closure

There are two options here, button-fly and zipper.  Do you want to take the time to completely unbutton your trousers every day, or not?  Simple.

The Pockets

First, decide if you want pockets and where.  Please, do try to spare us of cargo style pockets though.  The most common option has two front pockets (sometimes with a tiny pocket inside of one) and then two back pockets.  However, the important decision regarding pockets comes with “rear-branding”.  Do you want words or logo of a company stretching across your backside?  Probably not, so always check for that.


True Religion uses a lot of rear-branding in their designs

The Stitching

In most cases you are given two options: blue-thread stitching indistinguishable from the color of the jeans (basically invisible), or the classic contrasting golden yellow.  This is merely personal preference and one is not necessarily more formal than the other.

Yellow Stitching Levi's

Traditional yellow stitching on Levi’s. Courtesy of Long John


I am sure that you have noticed those little lines that go across the crotch of most jeans, and it is called exactly what it looks like, whiskering.  These are nice details that add character and depth to any wash of denim, particularly darker shades.  Avoid styles with excessive whiskering in professional settings.

Whiskered Look Jeans


A whiskered dark wash by Hudson. Courtesy of

Other Factors to Consider

Why Cuffing?

Not usually a built in feature, but definitely necessary in some cases.  Cuffing is an effortless way to work texture and dimension into your ensemble. Rolled or cuffed pant legs immediately take the formality of any outfit down a few notches and can enhance the overall fit of your denim.  Some styles may even incorporate a decorative trim inside to encourage cuffing so be on the lookout.

Cuffing Jeans

Great use of cuffing the break by

The Break

This is where the importance of cuffing comes into play.  Denim can work with or against your height, just like any other pant.  Break refers to the fold above the cuff of your leg and is created when the fabric of the pant reaches your shoe (if the style reaches your shoe).  Thus the pant line breaks.  A full break refers to when the pant develops a crease so large that a second break may ensue, and this is where sloppiness begins to show.  Avoid too many creases and breaks in your fit and utilize cuffing when necessary.

Get a Nice Belt

Sometimes getting a new pair of denim coincides with a new belt.  Think this through.  You want a belt that perfectly matches your shoes (unless you opt for sneakers) and you want to choose a shoe that gives you the nicest break – especially when choosing a pant for business-casual environments.  When we say the belt and shoes must match, we mean it.   Ensure that the colors match as closely as possible to add symmetry and balance to your formal inspired style.  Ideally, you want to match the texture of the belt and shoe as well.  For example, if you have a cognac pair of suede Chelsea boots then you should look for a suede cognac belt to match.

Why a Knit is Necessary

When dressing up your denim, it is not expected of you to show up in a tie.  However, some ties can really enhance your casual ensemble.  When choosing a tie opt for something that adds flair but does not outshine your situation.  This is why a knit is necessary.  Knits are casual ties that are oozing with cool; use them to dress up your casual outfit by layering with sweaters and blazers over your best denim.

Please feel free to view The Dark Knot’s range of Knit Ties!

Knit Tie with jeans

Knit ties can soften hard details like combat boots and moto jackets.  Look by Unkept Gentleman, Travis White – on IG @trav_white_

Knit Ties from The Dark Knot


As you are well aware by now, not all pairs of jeans are the same. 

Be mindful of the small details when choosing your denim as they can make all of the difference.  Carefully consider shoe choices before purchasing and tailoring your new denim, this will save both time and money.  Know when and where you plan to wear each pair and consider your existing wardrobe and style.

Fit and color play largely into how (and where) you might wear your denim.  Loosely fitted, lighter colored jeans are virtually synonymous with college wear, and graduating both literally and metaphorically to your next step in life often comes with a pair of dark fitted jeans.

And that's a wrap for this one! I hope that you have enjoyed reading this as much as we did writing it!

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