Men's Jeans - The Ultimate Guide

Frequently Asked Questions

6 Ways Men Wear Jeans Wrong

I see so many guys making the following mistakes, so I want you to be aware of them:

Too Baggy

Overly baggy jeans have an aesthetic that's unflattering, sloppy, and childish.

Basically, they make slim guys look skinnier and big guys look bigger.

Your jeans should fit your body type and be proportional to your build.

Too Tight

The right taper is important but overly tight is just plain wrong.

This makes you look both juvenile and unaware of how to dress well or for your body type.

If you're wearing jeans to work, it also looks unprofessional, regardless of how casual your work environment.

Too Light

Washes that are too light (very light blue or grey/white) or acid-washes are neither
timeless or versatile.

They ultimately make you look like you’re trying too hard to be trendy.

Keep your jeans in a clean, dark wash (color) or one of the other colors listed below.

Ripped

For 95% of men over the age of 25, distressed or ripped jeans are never a good look.

Like some of the lighter washes, these will make you look like a teenager.

A little distressing or fading is fine, but only if you’re under the age of 25.

Too Long

This looks sloppy and can ruin an otherwise good outfit.

It can make you look really short, which is not flattering at all.

Find the right length and go to a tailor, it’s a simple $5-10 fix.

Saggy Butt

Find the right fit in the seat – proper rise (discussed below), as well as how loose they are in the thigh area is crucial.

You want a trim (but not overly tight) fit.

Anatomy of Jeans

Here are some of the key things to look out for when shopping for your next pair of jeans:

Waist

Like all your pants, your jeans should fit perfectly around your waist with no need for a belt to hold them up.

The waist should sit a little lower than suit pants, so anywhere from the mid-to-upper hip area is where the waist of the jeans should be – definitely nothing below that. The goal is to ensure the waist sits where it doesn’t look droopy in the seat.

Rise

The rise is the measurement from the crotch seam to the top of the waistband, and the typical range is usually between 7-12 inches (17.75-30.5cm). The pant rise is an important factor as it determines the positioning of your pants on your body, ultimately influencing your perceived waistline.

There are three types of rise:

Low-Rise Jean
Unlike short and mid-rise jeans, low-rise jeans are not meant to conform to your natural waist but rather sit below it (more toward your hips). This style became popular during the 60s and 70s and has made a recent comeback with Gen Z.

Mid-Rise Jean
This is anywhere from 9-11 inches (23-28cm) and is meant to be worn at your natural waist. This is also called regular-rise or normal rise and is the most common rise you'll find on jeans. Ideally, this is the rise you should be going for.

High-Rise Jean

Typically defined as longer than 10 inches (25.5cm), high-rise jeans are a good option for men who are over 6 feet tall and who want to wear their pants at their waist, rather than at their hips. These can be found at any “big and tall” store or department, but make sure you have enough rise for a comfortable fit as these jeans are impossible to lengthen.

Seat

The butt area, AKA the seat, should lightly hug your butt and not be saggy or overly tight. If it feels like you’ll split your pants when you sit or bend down, they’re too tight. If it looks like you’re carrying a full load, you should probably try a different fit, and if that doesn’t work you need to get the upper thighs taken in by a tailor to compensate for the extra room in the seat.

Thigh

You should be able to pinch a minimum of 0.5 inch (1.25cm) of fabric, but no more than 1 inch (2.5cm) on either side of your thigh. If you can pinch more than that, try a different style of jeans based on your body type (see 'Best Jeans For Your Body Type' section below) or, if possible, go down a size. As a last resort, you can get a tailor to slim the legs to this size, but this’ll be costly.

Knee

The knees of your jeans shouldn’t fit too tight but lie comfortably close without feeling like it’s pulling tightly when you walk or bend down. There should definitely be no rips or tears around the knee area.

Break

The “break” of the pant is the fold or fabric crease that forms at the front of your pant leg while you're standing, (just above where the hem meets your shoe).

The image below shows the different types of pants breaks:

As a rule, your jeans should be long enough to have either a full break or a quarter break. These look much sharper and more polished.

If you have the perfect pair of jeans, but they’re too long, get them hemmed by a tailor to the proper length - this is usually no more than a couple of bucks and is totally worth it.

You should avoid jeans with a no break as this is just too short and can't be fixed by a tailor.

Color, Wash & Fading

Color and wash are basically synonymous at this point since they're used interchangeably by brands.

However, for the sake of understanding what it really means, put simply: denim that hasn't been washed is going to be darker in color since the dyes bleed a bit with each wash. So technically, a dark wash means unwashed or washed once. A light wash means... you guessed it, a washed pair of jeans. But in reality just know that when you see dark wash or light wash, it's just talking about how deep and dark the color is:

• Light wash = lighter colored.

• Dark wash = dark colored.

4 Essential Jean Colors To Own

The four colors of denim I recommend owning are dark indigo/blue, a medium blue wash, grey, and black. Anything outside of these colors will have very limited-use cases or not be appropriate depending on your age, height, skin tone, or body type. 

Dark Wash (Indigo Blue)

If you own just one pair, dark wash indigo blue is the one to own, so buy these first! It’s the most versatile and can be worn dressed up with something like a blazer and loafers or with everything casual like sneakers and a t-shirt.

If you work in a business casual office, dark indigo jeans are a great alternative to chinos on casual days.

Medium-Wash Blue

Not as versatile as a darker wash, I recommend a lighter medium-blue shade for more casual situations or for wearing during warm weather.

Be careful not to go too light on the wash as the very light shades tend to be a bit too trendy and can veer a bit too adolescent.

Gray

While not as important as dark blue jeans, grey jeans can be quite versatile. Stick with a medium to darker grey wash and don’t be afraid to dress them up.

Think of them kind of like a pair of grey chinos in terms of how and where you would wear them.

Black

I love a good pair of black jeans and they’re almost as vital to your wardrobe as dark indigo jeans. They also have a little bit of a rocker vibe to them and look great for nighttime occasions.

You can never go wrong with a pair of black jeans, a white or grey shirt, and a pair of sneakers or boots.

Different Types of Denim

Jeans are always made from denim, which is a cotton twill fabric known for its strength and its ability to withstand regular wear and tear.

However, it's important to understand that there are different types of denim to choose from depending on your personal style and desired level of durability or flexibility.

100% Cotton Denim

This is the original and most common type of denim. It's super durable and versatile and can be softer and more breathable than other types of denim. 

Raw Denim

This is a type of denim that has not undergone any pre-washing or distressing treatments. It is essentially the purest form of denim, in its raw and untreated state.

Raw denim enthusiasts appreciate this type of denim for its ability to develop unique and personalized fading patterns over time, as it adapts to the wearer's body. The absence of pre-washing also means that the fabric tends to be stiffer and requires some breaking in before it becomes more comfortable to wear. 

Selvedge Denim

Selvedge denim refers to a type of denim fabric that is woven on traditional shuttle looms. Unlike modern denim, which is often produced on large, automated machines, selvedge denim is woven slowly and meticulously on narrower looms, resulting in a unique and durable fabric. The term "selvedge" refers to the self-finished edges of the fabric, which are tightly woven and prevent fraying or unraveling.

Selvedge denim is known for its high quality and character, as the slow weaving process creates a tighter, denser weave and a distinct diagonal pattern known as the "selvedge edge." This type of denim is favored by denim enthusiasts and collectors for its authenticity and craftsmanship.

Stretch Denim

Stretch denim is woven with other fabrics to make it more stretchy and comfortable. Some jeans may have two to three percent spandex and others might have polyester blended into them. Stretch denim is known for its ability to retain its shape and provide a fitted look without feeling restrictive and it has become increasingly popular among consumers due to its comfortable and flexible qualities.

A quick thought if you go with spandex blends:

• Spandex blends, while a little more comfortable and forgiving in the thighs, tend to stretch out and not retain their shape as well as 100% cotton blends.

  • I’ve definitely seen some “poopy pants” as a result of this.

Common Styles or Fits of Jeans

Before going into the details of which jeans you should be wearing, we need to discuss the different styles of jeans (also known as the 'fits' or 'cuts') as you will want to pick the right fit depending on your body type.

Be wary of what the labels say as far as the fit is concerned as there is no universal naming scheme and every brand uses whatever they want in this regard.

Here are the most common styles (in order of slimness):

Skinny

Skinny jeans are characterized by their tight-fitting and slim-cut design.

These are typically made from stretchy materials such as denim or cotton, allowing them to hug the legs closely from the waist down to the ankles.

Slim

Slim-fit jeans are a popular style of jeans that are designed to fit closely to the body (but not as closely as skinny jeans).

These have narrow leg openings and snug fit through the thighs to the ankles.

Straight

Straight-fit jeans are designed to have a consistent straight cut from the hips down to the ankles.

Boot Cut

Bootcut jeans are shaped to drape over a pair of cowboy boots and are a mainstay of Western clothing.

They are fitted through the waist and hips and then gradually widen from the knee to the ankle. Only wear these with cowboy boots.

Relaxed

Relaxed-fit jeans have a roomier cut from through the leg and have become a popular choice for Gen Z and streetwear aficionados.

How Men's Jeans Should Fit

1. Your jeans should fit at your waist without a belt - even slightly too tight is OK as denim stretches with use.* 

2. The butt area, AKA the seat, should lightly hug your butt and not be overly tight or saggy.*

3. You should only be able to pinch 1-2 inches (2.5-5cm) of fabric on either side of your thigh. 

4. You should only be able to pinch 1-2 inches (2.5-5cm) of fabric on either side of the widest part of your calf.

5. When wearing sneakers, you want them to only have a slight or quarter break (See image below).
   Anything less and it’ll throw your proportions off. If you have bunching (more than a full break) around the ankles, this will have a sloppy appearance and make you look shorter, stockier or unkempt.

*Expensive to tailor so make sure that this area fits well off the rack.

Best Jeans For Your Body Type

Before we get into which cut you should choose, here's a quick note about height: It doesn’t matter.

My clients range in size from 5ft 3in to almost 7ft and I’ve never put them in different jeans because of their height. These are the best jeans for short men, tall men, medium-sized men, and so on. The only thing that matters is your build: slim/regular or larger.

Skinny, Slim, Short, or Regular Build

You’ll want to get a “Slim” fit. Slim-fit jeans tend to slightly hug the thighs, knees, and calves while tapering down from your knee to your ankle.

A lot of my slim and regular-build clients initially believe this style will make them look too skinny, which couldn’t be further from the truth. It’s just that they’re used to wearing baggier clothes to try and hide their slimness, which, coincidentally, just makes them look slimmer.

A properly fitting pair of jeans just looks right, regardless of your build, and doesn’t make you look one way or another – I promise.

Things to Avoid:

• Don’t make the mistake of thinking a “Skinny” fit is the same as a “Slim” fit.

  • “Skinny” fit jeans are usually skin-tight and not appropriate. Unfortunately, a lot of brands interchange the name of their cuts, so at least try them on.

• Avoid "Skinny Fit" jeans. They'll only make you look skinnier than you are - don't do it.

• Avoid “Straight Fit” jeans. As the name implies, the leg of the pants are looser and will be cut straight down from the knee to the ankle. This cut will look terrible on you.

• If you can pinch more than 2 inches (5cm) of denim on either side of your thigh and the widest part of your calf, you may need to move down to a slimmer cut or get the legs taken in.

  • If you can avoid it, don’t rush to the tailor. Try a size down first or another brand's slim cut. This is costly for a tailor to do and having too much fabric on your thighs or calf area will make you look smaller, skinnier, or shorter than you are.

Larger or Muscular Build

The classic “Straight-Leg” fit is perfect for you. It's all about balancing your body’s proportions to make sure your bottom half complements your upper half. Straight-legged jeans with a roomier thigh area, which will hopefully solve your frustrations with finding jeans that fit properly.

Things To Watch Out For:

• Avoid any cut of jeans (all pants in general, for your build) with a taper at the legs. A taper will make you look really top-heavy - like Humpty Dumpty.

• If you can pinch more than 2 inches (5cm) of fabric on either side of your thigh and the widest part of your calf, you need to move down a size, go to a different cut, try a different brand, or get the legs taken in by a tailor.

  • Having too much fabric on your thighs will make you look wider than you are and completely throw off your proportions.

Best Ways To Pair Jeans With Shoes

There are many combinations of shoes and jeans/denim you can wear, but depending on the shoes, your jeans need to be certain colors and fit certain ways in order to look their best, so let me show you the best ways to wear jeans with High and Low top Sneakers/Trainers, Boots, Chukka Boots, Chelsea Boots, Work Boots, Dress Shoes, Brogues, Monk Straps, Loafers, Penny Loafers and more.

Low-Top Sneakers

Due to the low profile of low-top sneakers, it's really hard to mess this up and they’ll work with almost any cut of jeans.

As for denim colors or styles, unless they’re all-black sneakers, you can pretty much wear any color or style you want.

The one caveat is that if you’re wearing white sneakers and dark indigo jeans, they can stain the tops of the shoes. So soak the pants in cold water for about 30 minutes to get rid of any excess dye that may rub off on the shoes and then spot clean the shoes, as necessary.

High-Top Sneakers

If you’re going to buy high-top shoes and wear them with the hem going past the tops of the shoes, you should just get a low-top pair of sneakers instead. It will literally look the same and low tops are more versatile anyways. I’ll assume you are wearing high-tops because you like the look of them and want to show off the whole shoe.

To do this well, either get your pants hemmed shorter, cut them with scissors for a frayed look to show off the shoes, or simply roll them to just above or below the top of the high tops. Never more than twice, though, otherwise you’ll have a really thick cuff on the bottom and it will look very heavy and throw off your look.

Athletic or Running Shoes

There are two schools of thought when it comes to athletic or running shoes, also called trainers and it depends on how “chunky” the shoes are. If they’re low-profile and sleek, then stick to a similar cut, as you do with low-top sneakers – which means wear any cut of jeans. You can even cuff your pants if you want a sportier look.

If they're chunky, you should be a bigger guy since these will require you to wear straight-cut jeans to fit over the thicker shoes. Otherwise, if you're thinner, your shoes are going to look really big and out of proportion with the rest of your outfit, so I say avoid it altogether unless you're explicitly going for that look.

Boots

Dress boots will pair really well with dark-wash or black jeans. Just make sure your jeans have a slight to no break to match the sleeker and more polished dress boots. Wearing dress boots and stacked jeans (lots of folds at the ankles) is like wearing tuxedo shoes with jogger pants – it just doesn’t look good.

Work boots tend to have a chunkier sole and a more casual appearance, so definitely play up the workwear version and wear them with dark wash denim or denim that has some fading. And cuffed or uncuffed, you can wear them any way you want. If you’re going for the super slim fit jean and chunky boot look, get them hemmed or roll them up to be shorter and leave no break. If you want a super vintage look, then try a single, oversized cuff and a more relaxed fit.

Desert and Chukka Boots

Wear your Desert or Chukkas Boots in any color and cut of jeans you prefer and they tend to look best with a slight or no break, depending on the look you’re going for. You can achieve this by cuffing your jeans or getting them hemmed.

Chelsea Boots

Chelsea Boots are not for everyone- if you’re a bigger guy, stick to work boots unless you want to look like Humpty Dumpty with little tiny legs. Chelseas need to be paired with slim jeans to look their best. The color and material of the boots will determine what you should pair them with.

If you’re wearing black leather or suede Chelseas, they’ll look best paired with black or gray slim or skinny jeans. Anything outside of this will be much harder to pull off.

For brown or tan suede Chelseas, especially with a gum sole, go with lighter blue or gray denim, which can also have some distressing.

Dress Shoes -
Oxfords, Derbies, Brogues, Wingtips, Monkstraps

Derbies feature a chunkier profile, so they’re better suited for casual outfits that include denim. Black derbies look great with black or dark blue denim, while brown derbies look great with dark blue or medium blue denim.

For brogues, as a general rule, the sleek, minimally detailed brogues will skew more formal, while chunky, hole-punched ones will skew more casual. The color of the shoes affects which jeans your brogues will or won’t work with, going from black at the formal end and getting gradually lighter towards the casual end will work best. Casual medium brown brogues pair well with indigo or lighter denim while other colors like oxblood and black will look good with black denim. As for cuts, they’ll work for any cut of denim you wear.

You can pull off Oxfords with black or indigo jeans, as long as they’re slim, and either cuffed or hemmed with no break so they’ll feel a little less casual, but still sleek and polished.

Loafers & Penny Loafers

The penny loafers’ low vamp (that’s the section of upper that covers the front of the foot) combined with a wide leg opening can make your feet look weirdly stubby. So opt for jeans that are tapered and cropped or pin-rolled. If you don't have the body to wear jeans with a slight taper, this look isn't for you.

As for colors, I love a medium brown pair that goes well with dark wash indigo but can also be paired with any lighter colors up to white denim. Black penny loafers will look great with gray, black, or indigo denim.

How to Wash, Dry & Care For Your Jeans

Washing

If you're looking to make your jeans last as long as possible, then you should only wash them when they smell or have stains. Otherwise, turn them inside out and air them out overnight or between wears.

When you do need to wash them:

• Turn them inside out

  • This will protect the color and minimize fading

• Use cold water and a mild color-preserving detergent

  • This will prevent any damage to the fabric.

  • Avoid using harsh detergents or bleach as they can weaken the fibers.

• Put them on a gentle wash cycle.

  • It is also advisable to wash denim jeans separately or with similar colors to avoid any potential color transfer.

Overwashing can cause the fabric to wear out faster, so it is important to find a balance between cleanliness and preserving the longevity of your jeans. Generally, it is recommended to wash them after every 5-10 wears or until there are visible stains. This helps to maintain their shape, color, and overall quality.

Drying

After washing, hang your jeans to air dry or lay them flat to prevent any shrinkage. It is generally best to air dry jeans rather than using a dryer, as this can help maintain their shape, preserve the color, and prevent shrinkage. 

Storage

Storing jeans properly is important to maintain their shape and longevity. The best way to store jeans is to fold them neatly and stack them in a drawer or on a shelf. Hanging jeans can cause them to stretch out and lose their shape over time. If you must hang your jeans, use clip hangers to avoid creating creases or marks on the waistband.

Outfit Ideas

Casual

This outfit could not be easier to throw together. Feel free to swap out the black jeans for a dark blue pair instead and the white t-shirt could always be changed up for a heather gray or navy version. Layer a mid-wash or olive trucker jacket or a navy bomber on top to complete the look if it's not too hot.

Elevated Casual

An Oxford shirt paired with jeans and sneakers has got to be one of the most fool-proof outfit combinations out there for an elevated casual look. The light blue Oxford works really well here, but if you wanted, you could always go for a white version instead. To elevate it further, throw on a blazer or bomber jacket and swap the shoes out for loafers, chukkas, or another boot.

Business Casual

We've got some expert-level business casual layering going on here. Notice the cut of the jeans here if you're muscular or bigger. This combo works for every body type and would also work if you wanted to remove the sweater, and went with the dress shirt only, just make sure you have a brown belt in a similar shade to the shoes. Speaking of shoes, chukka boots or regular lace-up boots could also work here, but they'd be a little less polished than dress shoes.