
Bottom line: It’s hard to look stylish, professional or mature if your clothes don't fit well. The easiest and most powerful thing you can do to improve your style is know the right fit for your body. Key rules of thumb:
Thin Man
Wearing over-sized clothing does not make you look bigger or broader — it actually emphasizes the fact that you don’t fill your clothing, or says: "I lost half my body weight on The Biggest Loser but haven’t bought new clothes since." Opt for "Slim Fit" clothing — and know that "slim" doesn't mean "metro." It simply means the clothing is designed to fit you well. If you want to look bigger: Opt for bold colors, bigger/wider patters, and use layering (ie: shirt, sweater and jacket) to visually "beef up" your physique.
Heavier Man
Here the truth: Loose, baggy clothing makes you look bigger, not smaller. If your clothes are too big, you're not hiding problem areas — you're emphasizing them. (Imagine a plus-sized woman in baggy sweats. What effect does that have?) To slim your look: Wear clothes that fit your body well; and opt for darker colors, smaller patterns and stiffer fabrics (ie: not "clingy"), which will smooth and slim your profile..
Shorter Man
You of all people want to avoid long, boxy clothing — this hides your arms and legs and creates a "stubby" look. To add height: Wear clothes that fit your body, rather than the size you'd like to be. (Having an "S" on the label is perfectly fine.) Opt for slightly shorter jackets; and whenever possible, wear a belt and tuck your shirt in, which will make your legs look longer.
Tall Man
Are you really an XL — or do you buy it for the length? If you're sacrificing fit for length, and wearing baggy XL or XXL sizes, it’s time to find different brands. You don't have to settle: many brands carry stylish "Tall" and Long" sizing. To balance out your height: Buy shirts and jackets with wider-spread collars, which make your shoulders look broader. Rolling your sleeves (whenever possible) will also “shorten” your torso area..
Muscular Man
Over-sized and "relaxed" fits hide all your hard work at the gym and makes you look shapeless. To clarify those broad shoulders are muscles (not extra pounds): Wear well-fitting clothing that tapers in at the waist, or creates the illusion of a waist, such as tailored jacket can. And be aware: while "relaxed" pants seem comfortable, they make your beefy thighs look "fat." Opt for Classic / Straight fit to maintain your sharp, masculine shape.
To demonstrate...
Last week, our Hendricks Park co-founder sent us this photo from an event in Cannes. While the photo quality isn’t great, the two men here give us a great example of Good Fit vs. Bad Fit — and the impact it makes on your overall impression:
Here’s what people really see when they look at you:

Let’s look at the gentleman on the left. Nice concept, poor fit. The jacket is boxy, and combined with his baggy linen pants — which are 2+ inches too long — the message he’s sending is: “I’m lazy and sloppy.”
(NOTE: While I love linen, it’s not ideal for travel, or events where you’ll be sitting a long time.)
Now look at the gentleman on the right. Even from behind, he looks sharp in a tailored jacket, straight-leg denim, and tan shoes (a much more stylish choice than black). Simply put, his clothes fit well. The message he's sending is: "I have my act together.”
Sometime today, squint at yourself in a mirror. (You may want to do this when no one's watching.) If you drew a line around yourself, what shape would you be? In other words: What is your clothing saying about you — or rather, what are you saying with your clothing?
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