The First Rule of Men’s Style (You Don’t Want to Break)

First things first: Ask any men’s style blogger or enthusiast what the single most important factor in dressing well is. They will tell you the same thing.

Fit is everything.

Clothing Fit | The First Rule of Men's Style | GENTLEMAN WITHIN

If there’s one thing I’d tell a guy looking to improve his style, it would be to build a wardrobe of clothing that fits. And by fits, I don’t mean super skin tight like compression gear. You want your clothing to fit your body well and be comfortable.

Way too tight clothes
Okay, you work out. We get it.

It really is the difference between looking sharp vs. looking sloppy. Here’s a simple infographic from Antonio Centeno of Real Men Real Style on how a shirt should fit for reference.

There’s no reason to wear ill-fitting clothing. Well fitting clothes creates a flattering silhouette, especially if you’re already in shape. Look around and you’ll see many men wearing clothes 1-2 sizes too large.

Comfort is one thing, but big, baggy clothes is/was never a good look, especially with dressier outfits. We don’t have to talk about those old JNCO jeans and Starter pullover coats.

Form-fitting clothing flatters, it enhances, and it instantly makes a man more stylish. [Tweet this]

Four Simple Things You Can Do to Nail A Better Fit:

1. Invest in a quality tailor

It took me years before I discovered the power of a tailor. I started with the basics. First my blazers, then my pants, then button-ups. Total game changer. I used to either cuff my pants or roll my sleeves up, and while that’s okay as a stylistic choice, it leans on the casual side. When going dressier, you’ll want a well tailored shirt and pair of pants.

A quality tailor makes a world of difference. If you’d rather buy new clothes instead of going to a tailor or think it’s not worth the investment, think of it this way. Would you rather have a wardrobe full of ill-fitting clothing or a few garments that fit impeccably?

Quality over quantity applies here. My buddy Brock from The Modest Man wrote an in-depth article on how to find a tailor.

2. Try a size or fit down

If you think you’re a large, opt for medium. Small? Try X-Small. You may find that it’s a better fit overall. For pants, if you’re more of a relaxed or classic fit kinda guy, try on the straight or slim fit, with a bit of taper down the legs for a more flattering silhouette. And for shirts, you’ll be surprised at how much crisper a slim or tailored fit can look on your body.

Dress shirt fit comparison
Which looks cleaner to you?

It may feel funny at first because you’re not used to feeling clothes that hug you a bit tighter, but get used to it because you’ll never go back once you see how much more stylish you already look.

Pants fit comparison
The difference is subtle at a glance, but clear. Notice how the slim isn’t so tight where it will restrict movement.

3. If it doesn’t fit, pass it on

You know what I’m talking about. The shirts that billow at the waist, giving you a muffin top appearance. The way too loose fitting khakis you bought for work at some cheap department store. The big puffy jackets that make you appear smaller.

Sometimes even the best of tailors can’t help you. In those cases you’re better off passing your clothes on to a relative. Or donate to a good cause. You want to get in the habit of curating and keeping items that fit and purging of all of your unflattering, ill-fitting pieces.

4. Stay active

I know this isn’t a style tip per se. But it’s valuable nonetheless. If you work in an office all day like me, you know that sitting for hours at a time is not helping one bit. In fact, studies show that desk jobs are killing us.

It’s best to get up and get moving, not just for our waistline’s sake, but our long-term health. Many of us know that we could be in better shape. Here are two free apps (RunkeeperFreeletics) that I use to help with my fitness goals.

So let’s start following through on our fitness goals. Start a routine. Hit the gym. Go for a run. Just walking a few minutes a day is helpful. Seems overly simplistic, but the more you get in shape, the better you will feel and the better your clothes will look on your body.

Remember, When it Comes to Good Style; Clothing Fit is KING

So there you have it, the secret to being a better dressed man. Focus first on the fit. It’s amazing what this simple shift can do to help you be more stylish. If I haven’t convinced you about the importance of clothing fit, let’s take a look at some comparisons.

clothing fit before and after
This often overlooked detail makes all the difference

When it comes to good style; Fit is KING. [Tweet this]

The one thing I urge you to do is to start wearing clothing that fits. It may take a little getting used to, but when you see the power of what a great fitting outfit can do, you’ll never go back. Plus you will feel a helluva lot better about yourself. Remember—look good, feel good, do good! And if you’re already on that train, then great, you’re already ahead of the curve!

Your turn. How do you feel about ‘fit’ when it comes to men’s style? Share in the comments below.

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  • Excellent article! Fit is definitely everything. And investing in a tailor certainly helps. Once you start wearing fitted clothes, you never want to go back. And as you mentioned, it has to fit well, doesn’t have to be tight to the point that it constricts your range of motion and level of comfort.

    • Thank you for reading! Can’t stress the importance of fit enough.

  • D-How

    Very interesting. I’m slowly making the transition to a slim fitted wardrobe. I’ll dress as well as you one day.

    • Thanks for dropping a message! It’s great that you’re transitioning the wardrobe. You’ll have to tell me all about it soon.