How To Wear Men’s Loose Fit Jeans And Shirts (Without Looking Like An Idiot)

by Barron Cuadro  |  in Trendy Fashion

Over the past year or two, you may have noticed that clothing styles have been getting a bit looser, wider, and oversized. We see it a lot in NYC and LA (and on Instagram), which means the trend will start to spread to other areas of the country over the next few years.

I see this as part of a more sweeping change of preferences and overall style that will probably last a while. Considering that trends re-emerge every 20-30 years, this swing towards baggier, looser silhouettes is right on time.

So what does that mean for your lean wardrobe, and for you? Do you have to buy new clothes, wear different things, and change your overall style now?

Short answer: No.

Longer answer: No, but consider this an opportunity to try new things and shift away from “all slim everything” as your default choice.

In this article, I’ll show you how to adapt to this change of loose jeans—looser, baggy silhouettes in general, including oversized shirts and outerwear—how to do it well, and how to incorporate it into your casual, smart sharp casual, and business casual style.


“Can I still wear slim fit jeans?”

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A standard slim fit jean or tapered jean still looks great in a business casual or smart casual wardrobe.

Not super skinny jeans, not jeggings, not skin-tight, painted-on jeans. Standard slim denim that looks fitted on you, regardless of whether it’s labeled “slim” or not.

But if you’re tired of all slim everything, this is your chance to branch out and experiment with a loose fit and more flowy (read: comfortable, interesting) clothing silhouettes.

The Problems With Slim Fit

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Since at least 2007, men’s mags and blogs have been preaching about slim and skinny fit.

A few years before that, the trend starters and early adopters couldn’t find skinny fit jeans in stores, so they were buying women’s jeans and squeezing into them. This was before denim companies saw the demand for a slimmer pair of jeans for men.

Men’s jeans have come a long way!

Fast forward a decade or so, and there are tons of slim fit options for dudes. However, there are a few problems with this idea of “slim fit”.

First, “slim fit” doesn’t mean the same thing for every body type. A straight leg Levi’s 501 model could fit slim on one guy, but look like baggy wide legs on another guy.

On top of that, slim fit is inconsistent among different brands. A pair of pants with the slim fit label at H&M or Zara is very different compared to a pair of “slim fit” pants from Lands End or L.L.Bean.

Second, anything too slim can be uncomfortable, especially with non-stretch fabrics.

Finally, a skinny / snug fit doesn’t look good on every body type, tbh. It looks best on skinny, tall dudes. Basically, the guys who in 2003 wanted to emulate that rock star chic look but couldn’t find jeans skinny enough, so they were wearing jeans marketed to women.

If you go too slim, but you don’t have the right body type for slim / skinny, and you’re trying to achieve that smart sharp casual look, well, it just doesn’t look right.

Going From Slim / Skinny Fit to Straight, Loose, or Oversized Fits

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All this to say, slim fits have had their moment in the sun for 15+ years. It’s no wonder the trends are moving towards looser styles.

So how does this apply to you, dear EG reader who has or is building a versatile lean wardrobe? Is this a trend you should pay attention to?

I’d say yes, and honestly, it’s for your benefit. Here’s why.

The Best Part About Loose Fit Jeans (Or Any Item Of Clothing)

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Let’s consider a pair of jeans, a staple in your classic lean wardrobe.

When you wear a slim, calf-hugging jean with a stacked cuff and boots, sure, it looks cool. It aligns well with a rugged, casual outfit.

But if you wear those same jeans with an OCBD and sport coat, there’s misalignment. It doesn’t look right, especially for a business casual look.

Overly slim suit pants and trousers are equally as awful-looking. If the wool cloth is clinging to every curve below your waist… your pants are too tight. A looser leg will look so much better.

Why, though?

The word for this is “drape”.

side view of men's suit trousers that fit well compared to suit pants that fit too tight
A pair of suit trousers I currently wear (L), vs. a photo of me in a suit from 2015 (R). Look how tight my suiting pants are on the right. Too snug, No drape.

The pants on the left lay better, have a higher rise, and are a nice shape from the waist to the leg opening. They fit well and don’t hug every luscious curve of mine.

Drape—how the fabric falls, how it hangs from and lays on your body—directly affects how good the garment looks on you. And this goes for everything, from shirts to pants, jackets to outerwear.

This is most evident in formalwear, which is meant to have a clean line from the shoulders to the jacket hem, and from the pants’ waist to the leg opening. When the fit is too tight, you start to get wrinkles and folds and puckering, the opposite of a clean line.

This man understands drape, fit, and detail. Follow @urbancomposition on Instagram if you want to learn how to wear a suit well.

When you have a suit that fits well (e.g. isn’t too slim, but instead, is cut and tailored to fit your body), or when you have a fuller cut pair of chinos, or a straight cut T-shirt, you can achieve a better drape.

How To Wear Loose Jeans (and Shirts, Outerwear, etc.)

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OK now that we’ve defined what “loose” means, and how to achieve drape with fuller cuts, you may want to give more relaxed, looser clothing a try. The thing is, you’ve been wearing slim fit everything the past 15 years, so how do you start to wear this more relaxed fit and actually look good doing it?

Here are some tips and pointers that will help you make the transition.

Find Inspiration You Can Relate To And Copy

Find photos and videos of guys in magazines (or on Instagram, Pinterest, YouTube, etc.) with a similar body type and see how they wear their relaxed clothing.

It’s one thing to see a model wear it, another thing completely to see someone who has a similar shape to you wear it.

One brand I like to follow that also understands and appreciates fabric, proportions, cut, and drape is Stoffa. Click through Stoffa’s Instagram to see what I mean.

Take It A Step At a Time With One Small Change

If you’re used to slim chinos, your first step should be getting used to a straight leg. You don’t have to go full on wide leg right away.

  • Spend a week or two in straight leg chinos and I guarantee you’ll get used to them in no time.
  • Spend a week or two in traditional fit T-shirts and sweaters, and I guarantee you’ll get used to them in no time.

Keep in mind that “straight leg” is another relative term. Normally, the fits escalate in size, like so:

Skinny Fit → Slim Straight Relaxed Loose Fit

But everyone is shaped differently, with varying proportions. Here’s an example:

  • If you’re 5’8″ (172cm) tall and a lanky 130 lbs (59 kg), a pair of jeans labeled “slim fit” may actually be your straight leg.
  • If you’re 5’8″, 190 lbs (86 kg), and can back squat 315 lbs (143 kg) in the gym every day, jeans that are labeled “relaxed fit” may actually be your straight leg.

Does this make sense?

Basically, don’t depend on the labels to tell you how your pants will fit. You have to try on several different sizes and cuts to find what works best for you.

My buddy Tim (@timDessaint on Instagram) looking stylish in his wide leg chinos from Dockers.

Wear Your New Clothes Around The House

If you’re not yet comfortable with relaxed pants or regular fit T-shirts, wear them around the house as you go about your day. Let your body get used to the feel, the freedom, and the lack of constriction.

It does feel weird at first, to not have fabric clinging to every inch of skin on your body, when you first start wearing more traditional fit stuff. It takes a bit of getting used to!

The good news is, as you wear your new garments around the house, you’ll get used to how they feel and after a while, it’ll be normal.

Give Yourself Some Time To Get Used To It

It takes a while to get used to new styles. Even for me, I’m not fully comfortable in anything wider than a certain fullness. Most of the time, I’m still thrown off by a traditional straight leg.

But I push it little by little, sit with it for a bit, and try wider styles when I’m ready.

three different fits of pants: loose, relaxed, slim tapered
The three pairs of pants I recently tried at Zara. On the right is my typical slim, tapered fit. I’m slowly getting used to a straighter leg (middle). On the left is a pleated wide leg denim I tried on just for fun 🤓

I recently went to Zara to try out a few different pant silhouettes (above): Pleated wide leg denim (left), relaxed fit chinos (center), and tapered joggers (right).

I’m used to the slim, tapered fit you see on the right. I’ve been wearing a similar fit for years.

I probably wouldn’t wear the pleated wide leg denim on the left, but it was fun trying them on. (Then again, never say never. I wore jeans like this 25 years ago when I was in middle and high school.)

As I push myself towards wider fits, my next step would be to wear the khaki chino pants in the center. I loved how these fit and lay on my body (plus, they had a higher rise, which looked awesome), but I’m not completely used to them yet.

So if you’re ready to push the limits of your comfort zone, do what I did.

Go into a fitting room and try on a few pairs. Buy the pair you’d like to get used to (in my case, the chinos in the middle). Wear them around the house to get used to them.

It’s a process!

You Will Feel Fat / Short / Skinny / Weird… At First

We all have our insecurities with our bodies, and how they look in clothing. Oftentimes we buy certain clothes or specific fits because we try to hide (what we consider our) imperfections.

So for example:

  • If you’re self-conscious about being skinny and you throw on a straight leg pair of pants, you might think they make you look even skinnier.
  • Or if you’re a bigger guy and you’ve worn slim jeans the past 10 years, you may think a straight leg pair makes you look fat.

This goes back to wearing your new clothes around the house first, so you can get used to how they fit and feel. When you try a new style or fit, it doesn’t feel quite right. It takes you some time to acclimate.

man wearing grey pants with a denim jacket and with a suit jacket
A simple pair of wool trousers worn two ways: casual and “business casual”. Notice how my legs have room to breathe? the pants are fitted but not overly slim, the rise is higher, and the cuff rests perfectly at the top of my shoe with the most minimal of breaks.

I felt the same way about higher waisted trousers when I first tried them. I always thought I had a short torso, and so when I wore high-waisted trousers, it made my torso look even shorter.

But then I found some inspiration (guys in similar shape as me wearing it well) and the more inspo I collected, the more I felt confident doing it. Once I tried it, I swear I can’t go back. Higher waisted trousers look better, drape well, and are more comfortable.

Same goes for pleats, and relaxed or straight leg pants. I had to go through feelings of uncertainty with those styles, too.

So give it some time, even if you feel the looser stuff doesn’t look right on you yet.

How Your Relaxed Fit Pants And Shirts Should Fit

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Style rules aren’t laws set in stone.

They’re more like widely-accepted suggestions that, if followed, will get you to the point where you have a pretty good, base level personal style.

Things like “only fasten the top button of a two-button suit jacket” and “don’t wear a black leather belt with brown leather shoes”“.

Some are worth following (the former), some can be bent and / or broken (the latter).

Good Style Is Like Cooking Your Favorite Dish

The first time you ever cooked your newly-discovered favorite dish, you had to follow a recipe step by step to recreate it. Maybe your mom or dad taught you how to make it, and you followed their directions exactly.

But after your 50th time making your favorite dish… you’re probably not following the recipe at all. You can cook it half asleep, with your eyes closed, and one hand behind your back, because you know it by heart.

In fact, you’ve probably added and removed a few spices, and combined a couple steps over the years. You’ve improvised and improved it. You’ve made the recipe your own.

There Is No One Correct Way To Wear It

Style works much the same way.

Once you know the recipe (i.e. the “style rules”), you can improvise. After following the rules for months or years, you know which ones to bend, break, or ignore completely… all to create a personal style (i.e. a dish) that’s your very own.

All this to say, there is no one formula that shows exactly how your relaxed fit clothing should fit on you. It depends on your height, your build, and what look you’re trying to achieve.

This is why finding inspiration, copying and trying a few things yourself, and then iterating on that experience is so important.

How I Wear Looser, Relaxed Fits

Here are some of the guidelines I’ve created for myself when it comes to wearing looser, more relaxed clothing:

For pants, I want a no break or cropped hem. This goes back to the idea of drape and clean lines. I prefer a clean line so that even with a more voluminous leg, the overall look is still very sharp and streamlined.

If I’m wearing relaxed fit jeans that are also long, that’s more of a 90s-2000s hip hop aesthetic, which isn’t “wrong”, just a different style than what I’m going for. Refer to the photo of my Zara try-on sesh above, or this Insta 👇

Kim (@blvckd0pe on Instagram) does that oversized, streetwear, high end hip hop aesthetic well. Worth a follow if you want to broaden your exposure to different styles!

For shirts, I still buy my size, just in a traditional or oversized fit. This ensures the shirt fits me correctly in the shoulders and is the right length, while still having more room in the chest and torso.

I’ve come to appreciate the traditional cut shirts, especially with OCBDs and other woven sport shirts that don’t have much stretch in them. It’s a much more comfortable style that I can wear all day long.

And with looser-cut Ts, I appreciate the freedom from restriction, and the feeling that the shirt is always clinging to me… I hate that.

asian man wearing light blue jeans and a yellow polo
How I prefer my jeans most days: fitted, but not overly tight. If it’s hugging my calf, it’s too tight.

You may be tempted to simply size up 1-2 sizes for a looser fit. This can work sometimes, depending on the garment. It’s really a case-by-case basis sorta thing.

As much as possible, I like to find things that are my size, but cut in a boxy, more traditional fit. Again this ensures a better fit (oversized in the way the designer intended), vs. just sizing up, which can look sloppy with slightly off proportions.

The nice thing is, it’s easier to find loose, relaxed, oversized cuts nowadays. More and more brands are designing these silhouettes, which should make it easier for you to find and try this style.

Loose Up Top, Fitted Down Below (And Vice Versa)

When you’re experimenting with looser fits, having a loose-fitting top and a voluminous pair of pants can feel somewhat overwhelming. In that case, I suggest alternating between loose and fitted.

So if you have a wider straight leg jean, go with a standard fitted tee. If you’re doing a voluminous, oversized sweatshirt, go with a slimmer pair of denim.

Good example of (relatively) fitted up top, loose down below. Check out Greg’s Instagram; this man knows how to play with clothing silhouettes and proportions.

This is a good way to dip your toe in the water, so to speak, of looser fitting clothing. The easiest combo to try first would be a relaxed top (anything from a T-shirt to a sweatshirt to an oversized outerwear piece) and a slim / fitted pair of pants.

Loose, Relaxed Fits and The Smart Sharp Style Aesthetic

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It’s easy to see how wearing looser, more relaxed fits can work with a casual wardrobe consisting of T-shirts, denim, chinos, sweatshirts, and outerwear.

But how does this play into your smart, sharp style?

What if your typical outfit consists of dark denim, an OCBD, and a sport coat? Should you start wearing oversized blazers, baggy OCBDs, and wide leg denim?

Well, of course not, but you can still incorporate this loose silhouette idea into your smart casual / business casual aesthetic, for sure. The term used in the business casual / smart casual world would be “traditional fit“.

asian man wearing a nice navy suit and a closeup of the trousers and shoes
I’d consider my Spier & Mackay suit to have a more traditional cut and proportions. It’s a classic. Read more about why I recommend SPier & Mackay.

I mentioned this earlier, but over the past 15ish years, menswear has been trending towards slimmer and slimmer fits. It’s a very cyclical thing; we see this happen every 20 years or so… this shift between slim and form-fitting, and loose and voluminous. We’re currently swinging towards looser fits again.

The problem with really slim cuts for dress clothing like suits, sport coats, and trousers, is you lose the wonderful drape that these garments should have. I mentioned this earlier in the article.

So really, embracing a more traditional fit just means swinging back to the specific cuts and silhouettes suits and sport coats were meant to have.

Simon Crompton (@PermanentStylelondon on Instagram) showing us how chinos should fit when wearing a smart sharp casual outfit. These are bespoke and fit him perfectly, however, a similar, “good enough” fit can be achieved with off-the-rack chinos if you look hard enough (and try on many pairs).

If you’re wearing jeans with a sport coat (one of my go-to dressy casual combos), go for a straight fit jean or a regular tapered fit.

To make sure the outfit looks clean and is styled appropriately, the jeans will look best with no break (or cuffed, so they have no break). Having no break will maintain that clean line from the waist to the hem.

Same rule applies to your chinos as well, if you decide to go with khakis and a sport coat.

Which Brands Sell Men’s Loose Fit Jeans, Chinos, Shirts, and Outerwear?

Nowadays, relaxed silhouettes are more available than ever!

Here’s a quick list of my favorite brands that will carry loose fit jeans and chinos, relaxed silhouettes, traditional fit tees and shirts, and oversized outerwear.

Brand / StoreSpecializes In
ZaraAffordable fashion-forward men’s clothing
COSMid-tier fashion-forward men’s clothing
Alex MillMid-tier basics and essentials
UniqloAffordable basics
InformaleHigher-end casual tailoring
ASOSAffordable fashion-forward men’s clothing
StoffaHigher-end trousers, outerwear
CasatlanticMid-tier full cut trousers

I find great brands and stores all the time. I’ll be sure to add to this list as I find them!

Relaxed Fits Are Here To Stay, So Give Them a Try

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Based on how styles trend over time, I’m betting that more relaxed fits are sticking around a while. Personally, I think that’s a good thing! We needed a change after 15 years of “all slim everything”.

Does this mean slim = bad? Of course not!

Especially not for you, an EG reader and Lean Wardrobe enthusiast.

A trim, slim fit will always look good. But use this swing towards looser and more relaxed silhouettes to try something that isn’t so tight (assuming you’ve been wearing slim pants and shirts this whole time).

Relaxed fits tend to drape better. You’ll get more movement in your clothing, and you’ll be much more comfortable and less restricted.

No matter if you consider yourself too skinny or too big, too short or too tall, having a more comfortable fit is important. You can be comfortable and look sharp and stylish, it’s just a matter of doing it well.

Questions? Hit me up on Instagram DMs (and feel free to follow while you’re there!)