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Modern Oaks is a fashion and grooming blog that provides versatile style inspirations for men. Our goal is to keep men fashionable,  presentable, attainable, and desirable.




Aaron x Andrews

Being forced to wear a button-down shirt in an office setting can be an intimidating feat. For the most part, most men opt to wear collared shirts in its traditional fashion (tucked in while leaving the top button un-buttoned for a more ‘casual’ appearance.

Unless you work in finance, government, sales or law (where traditional wardrobe is strongly encouraged) the button-down carries a lot of versatility.

Here ae three styling options that will expand your button-down looks:

1. Untucked

Not every collared shirt is meant to be worn untucked. There are three tests that I always consider when determining whether it’s ‘safe’ to wear my collared shirt in an untraditional untucked fashion.

1. Length of the shirt

I try to go by the rule that an untucked button-down should hit your wrist. Any longer than that then you’re stepping in trendy longline territory… any shorter and you may want to adjust your size.

2. The cut of the hem

Most off the rack (OTR) button-down shirts that are sized by collar and sleeve length are cut longer in the front and back, to ensure your shirt stays tucked in when siting down and bending over. While shirts that are cut even all around can be worn either way, they often look cleaner and more organic when they are worn untucked.

Now this isn’t to say that shirts with x cuts aren’t to be worn “untucked,” they can be. One rule that has always kept me honest is purchasing button-down shirts that are sold in a general US sizing (S,M,L, etc.). The tails are not as dramatized because designers want these pieces to have versatility.

3. Fit of the shirt:

Classic fitting shirts (most often the ready to wear dress shirts that you purchase from department stores) are fit to appease American standards. That being said, traditional shirts are not slim fitting and flare at the hem.

Try to avoid wearing these shirts untucked as the fit is often unflattering and resembles an oversized appearance. Oversized may be the in look for t-shirts, but you don’t want to be drowning in a collared shirt.

Depending on your build, consider purchasing slim fit or euro fitting collared shirts as they fit a little closer to home. Avoid muscle fits or skinny fits (there are some things that look just as unflattering as oversized clothes and that’s a shirt that’s too tight).

2. Open with an undershirt

This is one of my favorite looks. I will say this one does look the most relaxed, but that shouldn’t deter you from exploring ways to incorporate it at work. To execute this look, consider complimentary tones and/or incorporate patterned shirts to break up the shirts consistency and pair it with a white shirt.

Button-down shirts that have hints of grey, black, and white are always a safe bet. Feel free to add a little color to your wardrobe and consider sporting green pants or blue jeans to update your look.







3. Tucked and UNbuttoned

Yes, the premise of this post was to get you to untuck your shirt. However, if you’re not comfortable stepping into a meeting without having tightened up your look, there’s still another option.

Patterned short sleeve shirts were all the craze this summer. To extend the life of the Cuban inspired look:

  1. Tuck it in
  2. Throw on a white shirt
  3. Let at least three/four buttons free
  4. Pair it with a statement shoe and belt.

Yes, this the most detailed oriented style to execute, but it is the most unique if you invest the time and energy this look demands.

For starters, try keeping it simple with black and white. A black button down and white shirt is a versatile and casual color combination. While a clean pair of white sneakers on Friday are acceptable, test your comfort limits and pair it with a brown or black Chelsea boot.