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Dress Like a Man

Updated: Nov 27, 2018

Everyone loves a makeover, but they’re usually aimed at women. What gives? One of my favourite movie makeover montages, however, is from Crazy Stupid Love with Ryan Gosling and Steve Carell. It inspired me to write.

Dress Like a Man

Not like a boy and not like your grandpa.

Gentlemen, we all know you can’t go wrong in a well-made suit. But can you look sharp while being comfy casual? Hell yah!

Just to be clear, when I talk about boys, it’s not necessarily about age, but maturity. Think of those would-be frat men who are 40 going on 14. Yuck.

On the other end, “grandpa” is a mentality, not an age. He’s given up on personal style. His last fashion buy was when Clinton was president, and even then, it was two sizes too big. He believes comfort and style are mutually exclusive.

Don’t despair, guys. Finding the right clothes isn’t advanced calculus. An easy test to weed out the don’ts before any purchase is to ask yourself: would a boy wear that? Would grandpa rock it? If the answer is yes, put it back!

When looking for good clothes, here are some basic pointers every man should know about comfortable style. Let’s get started from the top. Go for quality fabrics with good drape that will accentuate your body type, so stay away from thin, threadbare materials (especially if you’ve got moobs) and avoid extra thick or chunky (it’s more frumpifying than fashion). For example, to downplay your dad bod, a skimming shirt will work better than a clingy jersey tee.

Next, whether it’s a spiffy button-down or a simple T-shirt, make sure it fits properly. Baggy looks sloppy; too tight highlights every lump and bump while making you look larger (why else do you think the gay boys love their clingy clothes?) which, unless you’ve got guns and abs, will make you look more bursting bulges than fashionably fit.

Don’t be like Boys with:

-Graphic tees/slogans and logos

-Over-sized baggy fit

-Busy, douchey embellishments

Don’t be like Grandpa with:

-Over-sized golf shirts

-Baggy t-shirts

-Bowling shirts

-Thick sweaters

-Loose cardigans

-Tucked in t-shirts

-Tan and taupe colours

Men dress for success. Good fit is key, not too baggy or tight. Quality materials that are not too thin, not too thick.

-T-shirts in solid colours, v-necks and Henley necklines

-Clean stripes

-Fine knit sweaters

-Well-fitted dress shirt. You can never go wrong with a crisp, clean white shirt!

Now we’ll tackle the waist down. A well-fitting pair of pants accentuate the positive and glide over the negative. A lot of gals are a butt-woman, so a great pair of jeans that frame the caboose will turn heads.

Don’t be like Boys with:

-Over-sized saggy, low-riding jeans or Hammer-time crotches

- Badly ripped denims

-Baggy sweats

-Hems puddled around the ankles

-Embroidery, studs, any embellishments - this includes acid wash!

Don’t be like Grandpa with:

-Pleated khakis

-Pleated anything

-Comfort waist bands

-Baggy and saggy

-Sweat pants

-High-waisted trousers

Men bring out your best booty with:

-Jeans and pants that fit to the body type - Skinny, slim, straight, loose

-Hemmed to the correct length

-Simple, clean design

-Solid, dark colours

-Always flat front

Shoes can make or break an outfit, so put your best foot forward. Dirty, beat up footwear will ruin any look. Trust me, women notice shoes.

Don’t be like Boys with:

-Chunky soled trainers if you're not at the gym

-Overly bright, colourful footwear

-Loud logos

-Exaggerated shapes - too pointy, too square

Don’t be like Grandpa with:

-Sensible runners/trainers

-Comfort shoes


Men show you care about your footwear with:

-Casual, sporty, chic styles: Go for streamlined designs; without the heavy feel of a trainer. You can’t go wrong with the youthful, classic appeal of Chuck Taylors

-Boots: Stick to the tried and true. Desert, Chukka, Chelsea, and Moto are all classic boot styles that will never be a misstep

-Dress shoes: Quality over quantity. Classic over trends. Whether lace up or loafers, keep your eyes on the toes - not too pointy (elf-like), not too square (stumpy club foot), not too round (think Bozo). A carefully chiseled or slighted rounded toe works best

- Wear brown shoes with blue jeans, khakis or tan coloured pants; black shoes with most other colours

-Slim cut pants look good with most footwear. For wider cut legs, go for chunkier shoes

So, did you catch an ongoing theme with these style tips? The key is always fit. Find a cut that flatters your body type. You want classic, well-tailored, well-made designs with quality fabrics to have you looking and feeling your best. A great outfit will have you standing taller and feeling like the Master of the Universe!

Still at a loss? Find a celebrity who has your body type and shares a similar fashion sense. Follow his look. When you go shopping, notice how the mannequins are dressed, and consider purchasing the entire outfit. Shop with a friend whose style you admire and will give you an honest opinion. It might seem daunting, but thankfully, men’s fashion aren’t fickle like women’s. If you follow the above tips correctly, taking control of your style doesn’t mean you need to shop every season. The right pieces will last you for years to come.

From workday to weekend, here are a few simple styles you can steal inspiration from.

I won’t take age or size as an excuse for not looking your best. Here are some great looks for larger men.

For more mature gents, these stylish ensembles will put a spring in your step.

The most important part of your wardrobe is confidence. The right outfits will bring it out in you. Now who doesn't want to dress like a man?

PS. I had never given much thought to a vest, until I saw Ed Sheeran's Thinking Out Loud video. If a vest can make him look dashing, think of what it will do for you. Vests taper the waist, broaden the shoulders and camouflage the paunch. Caveat: please don’t wear with a t-shirt underneath! You're welcome.

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