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7 Easy Ways to Upgrade Your Guy’s Wardrobe Without a Fight!

Shortly after we were married, my wife (strongly) suggested that we overhaul my wardrobe. Apparently, she was not impressed by my closet, which contained about 50+ free t-shirts and a few pairs of jeans that I’d been wearing since high school.

I had just started working full-time, so most of the new clothing I acquired was fairly dressy. At that point, I only wore casual clothing once or twice a week.

But then six months ago, I left my job to start a MBA program, and quickly learned that my casual wardrobe was still sadly outdated (you’ll see what I’m talking about in the pictures below).

I told my wife that we needed to make some upgrades (ideally without breaking the bank). I’m not interested in pushing the limits of fashion — I don’t want to look like I’m trying too hard— I just want to look put-together and not have to worry about what I’m wearing after I walk out the door.

If your boyfriend or husband is still wearing the same items of clothing that he owned in high school, it might be time for a change. And if he’s like me, he won’t mind, as long the changes are fairly subtle. Subtle is key — you have to let him know that you’re not trying to make any major changes! He doesn’t have to expect an entirely new wardrobe — just a few very small shifts. And just remember that his comfort is key, as well! He can keep the jeans and t-shirts, but it might be time to retire the ones that are older then Justin Bieber.

Who knows? He might not even notice them at first, but these 7 fixes make a BIG difference. They’ll help him look put-together, without too much effort. Plus, once they’re in place, you can point out how much better he looks, and then he’ll really be sold.

  • 7 Subtle Ways to Upgrade Your Guy’s Wardrobe 1 of 15
    Wardrobe Upgrade

    And the cool sunglasses are optional!

  • Problem #1: Baggy Jeans 2 of 15
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    If you're going to make one change, make it the jeans. The days of baggy jeans are over...for now! 

  • The Fix: Try a Slimmer Fit and a Darker Wash 3 of 15
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    Try going a little skinnier. No need to be skin-tight, but a slim fit is much more on-trend. A darker wash also makes it easier to dress jeans up or down. 

    Buy Levi 511 Jeans for $40 on sale

  • Problem #2: The Sneakers That "Go with Everything" 4 of 15
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    When I put these on, I told my wife, "These don't look so bad." Then I saw the photo, and abruptly changed my mind. They make my jeans bunch up excessively and call too much attention to my feet. Not in a good way, either.

  • The Fix: Ditch the Sneakers for Nicer Shoes 5 of 15
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    There are plenty of stylish AND comfortable shoes out there, and jeans will hang a lot better with non-athletic shoes. I'm a particularly big fan of loafers or driving shoes.

    Purchase a pair of Cole Haan loafers for $158

  • Problem #3: The Beloved Old Tee Shirt 6 of 15
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    A t-shirt like this is not bad, but it is kind of boxy. The shoulders are slightly too big, and the way this stiff fabric holds wrinkles makes it look like I just pulled it out of the laundry basket. Nobody wants to iron their t-shirts, so it's time for an upgrade.

  • The Fix: Pay Attention to the Fit 7 of 15
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    T-shirts, even ones with graphics, can look great. But he has to learn that if there's only an XXL left and he's a medium, then it's time to walk away. Help him learn this lesson by showing him the value of the correct size. Look for ones in a really soft fabric, sometimes referred to as "vintage wash," because they'll hang better and they don't have that same boxy look of a stiff fabric. Then toss those free t-shirts that don't actually fit, in the trash. 

    Buy a similar tee at Target for $10

  • Problem #4: The Boring Sweater 8 of 15
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    This sweater has no shape, the neck is too wide, and it hangs like a drape. We can do better, folks.

  • The Fix: Pay Attention to the Details 9 of 15
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    The zipper makes this sweater more interesting, and the band at the hem keeps it from looking like a t-shirt. You might have to pay a bit more for these details, but they're worth the expense. It's all in the details, and he'll pick up on this soon enough.

    Buy a similar sweater at J.Crew for $59 on sale

  • Problem #5: The Too-Casual Jacket 10 of 15
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    This jacket is great for a workout, but not so great for anything else.

  • The Fix: Go for Something Simple and Structured (and Not Made of Nylon) 11 of 15
    Upgraded Jacket

    A real jacket has more structure, and can easily be dressed up or down. It looks equally as good with a dress shirt and slacks, as it does with jeans and a t-shirs. Try to imagine it paired with different outfits: Can he wear it to work? Can he wear it on the weekends? These are great questions to ask! It keeps it very simple for him if he only has to work with one piece.

    Buy a similar jacket at 6pm for $80

  • Problem #6: The Sports Watch 12 of 15
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    Guys don't tend to wear a lot of extras. Since a watch might be his only accessory on a daily basis, don't blow it with an ugly plastic timepiece.

  • The Fix: Think More Metal, Less Plastic 13 of 15
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    I used to think of this solely as my "work watch." Now I realize it's the other way around; my "triathlon watch" is solely for triathlons.

    Buy a similar watch at Target for $80

  • Problem #7: The "Standard Fit" Button-Down 14 of 15
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    It may not look like it, but this shirt truly is "my size." Unless he's big enough to really fill out the chest and sleeves on a standard-size shirt, most guys will look like they are drowning in these dress shirts. When you're dressing up, the last thing you want to do is look like you borrowed someone else's shirt, or like you're 10 pounds heavier!

  • The Fix: Upgrade to the "Tailored Fit" Instead 15 of 15
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    Try tailored fit dress shirts, like the ones from Lands' End or Brooks Brothers. They still come in the same measurements (16 x 33, for example), but they'll be called "tailored fit" or "slim fit." They don't drown a man like the standard fit will often do; they'll keep him looking sharp!

    Buy a good tailored shirt at Lands' End for $54

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