You want to look trendy and show off your style by joining your buddies who wear their dress shirts untucked. The problem is that not everyone can pull it off. Wearing your shirt untucked may be a trend in men’s fashion, but it simply doesn’t work for every shirt. Knowing a few rules about shirt hemlines will dictate whether you should wear it in or out.

Tips for wearing your shirt untucked vs tucked in

Check the hemline

Shirts with straight or “even” hemlines can be worn tucked in or out depending upon the style, fabric and how casual you want to appear. We’re talking knits, polos, tees, short sleeve button downs or Hawaiian prints. Tuck them in to show off that great belt buckle or let them hang out to catch the next breeze. Wear loose fitting shirts untucked but beware—there’s a fine line between being too loose as to appear sloppy and being trendy.

Pay Attention to length

Shirt length is another important consideration for wearing a shirt untucked, it has to be just right. The front should just cover the belt. If it hangs over the entire crotch area, it’s way too long. You can wear a sport coat over an untucked shirt, but the shirt needs to an inch shorter than the coat so the shirt bottom can’t be seen. After all, you do want to show off your fashion sense. And also know when button your jacket.

Classic Dress shirts should be worn tucked in

Classic off-the-rack dress shirts have curves at the bottom of the side seams, forming “tails” which are longer in the back than in the front. They can have excess material and leave you looking as if you’re wearing a nightshirt. So please try to avoid.

We Make Custom Untucked Dress Shirts…it’s a thing

We have seen a huge increase in the amount of clients requesting their custom dress shirts be shortened in order to wear them untucked with jeans. Typically we advise they fall halfway down the fly in front and seat in back. This allows them to look great with a pair of jeans or khakis, yet still be long enough to be tucked in when wearing a suit. Which means you don’t need a set of each.

Man wearing custom dress shirt untucked with blue pants|SW Wilson Custom Clothiers Phoenix AZ
A custom made untucked dress shirt will not only fit perfectly according to your own measurements, it will have all of the design elements chosen by you. You could have contrasting collar bands and cuffs along with a gusset placed at each side seam. It may cost a little more but the details will give you a one-of-a-kind look that works for both casual fashion statements and business attire.
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