Man Makeovers: 3 Self-Proclaimed Dorks Get Major Style Upgrade

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Playing Extreme Clothing Makeovers: 3 Men Take Their Styles From Dorky to Dashing
Extreme Clothing Makeovers: 3 Men Take Their Styles From Dorky to Dashing Aired August 12, 2019

When we have a man in need of a makeover on our show, we like to call on lifestyle and fashion expert Tommy DiDario.

Whether it's a man whose wife wants him to stop wearing clothes that are too big or a dad who actually calls sweatpants dressy, Tommy has helped more than a few men realize that looking great doesn't mean you have to sacrifice your comfort.

Today, we've got not one, not two, but THREE man makeovers courtesy of our friend Tommy. And not only did Tommy give each of these self-proclaimed "dorky guys" a major style upgrade, but he also shared some super helpful general tips for picking out and styling clothes that will work for you.

"A lot of guys think that a well put-together outfit automatically means it's not comfortable — and that's just not true," Tommy says. "You can look like a million bucks and be so, so, so comfortable. And that was my challenge today — to show them [that]."

RELATED: Dad Who Calls Sweatpants "Dressy" Gets A Comfortable Makeover From Son

Daryl was nominated by his wife, Lynn, who says Daryl "thinks he's an '80s basketball player."

Here's Daryl's before look, which Lynn says he has pretty much "always" had.

Makeover Before Photo
Rachael Ray Show

The fashion pro swapped Daryl's sweatpants out for a pair of chinos, which he says are super soft, comfortable and flexible. "They're tapered throughout the leg so you have a really clean silhouette and they don't bunch at the bottom," Tommy says. "They probably are your most comfortable pant aside from sweatpants that you can dress up or dress down."

Makeover After Photo
Rachael Ray Show

Expert Tips for Styling Chinos:

  • Wear your chinos so they fall about two inches below your belly button, right above the hip bone.
  • Tuck your shirt in to create a clean, even line — you'll look long, lean and tall.
  • Chinos do not require a tailor! 

Jeff, whose daughter Cayla says he picked her up from a party wearing this outfit, loves to wear his flannel PJ pants and slippers out and about.

Makeover Before Photo
Rachael Ray Show

Tommy "flipped the flannel," giving Jeff a lightweight flannel shirt to wear tucked into a pair of fitted jeans.

Makeover After Photo
Rachael Ray Show

Expert Tips for Wearing Flannel:

  • With flannel shirts, lightweight is key — make sure you don't feel like your flannel is weighing you down. 
  • Fit matters! Your flannel should be fitted (not too big) and should fall no lower than your hip bones (not too long).
  • Go for earth tones like green, burgundy and gold.

Teddy lost over 240 pounds, but he's still wearing the same clothes — which are way too big!

Makeover Before Photo
Rachael Ray Show

Tommy expressed the importance of knowing your clothing size. "If you wear clothing too big, you can look 10 to 30 pounds heavier than your actual weight," he says. 

Makeover After Photo
Rachael Ray Show

How To Tell If Your Clothes Fit Correctly:

  • For your pants, use the 2-finger rule. If you put two fingers in your waistline, you should be able to fit them comfortably, but not have a lot of room to move anything else around.
  • For your shirt, look at your shoulders as your benchmark. If you can grab about 1 ½ - 2 inches of fabric and move it forward and backward, you're wearing a size that works. If you can grab a big bunch and move it all around, it's too big.

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