You’re getting dressed in the morning. You’ve got all the elements of a great, casual outfit. Great-fitting jeans? Check. Clever t-shirt? Check. Seems simple enough, right? I mean, just put it on and get out of the house. But with a look in the mirror, you’ll discover your simple outfit brings a big – albeit not earth-shattering – dilemma. Should you tuck in that shirt or not?

If you’re like me, you’ve gone the ‘experimentation’ route with your shirt. You don’t want to wrinkle your shirt, so you fold it under to get a good idea of what it would look like tucked in. If you squint your eyes, you can kind of tell. Then you unfold it and look at the un-tucked version. After a few rounds of this little game, you give up and just go out. But what if you could skip it altogether? What if there was an ultimate guide to when and whether you should tuck?

Well, here we go!

• Let your feet guide you. What kind of shoes are you going to wear? If it’s sneakers, you can definitely go either way. If you’re wearing pumps or high-heeled boots or sandals, you should probably tuck. If you’re wearing preppy-looking shoes, like loafers, you should definitely tuck. If you’re wearing hiking boots or something else that’s kind of rugged, don’t tuck.
• What does your waist say? If you’re going to tuck, you’ll probably need a belt – and that brings up a whole new issue. This issue can be solved by the size of your waist. If your waist is trim, you can always get away with tucking. If you’re suffering from “Dunlap Disease” (as in, your belly done lap over your belt), you’re almost always going to want to go untucked to help camouflage that little snack pack you’re carrying.
• What else are you wearing? If you’re wearing jeans, you could go either way – depending on your figure or physique. If you’re fit, tucking will show off your hard work. If you’re unfit, tucking will show that, too.
• Where are you going? If it’s casual Friday at work, you absolutely should tuck. Tucking looks neater than not tucking, and you’re there to work – not to shoot pool. You don’t want that “just rolled out of bed” look at work ever. Show up like that, and your boss, co-workers, and clients will all wonder about your competence. Tucking is your only option here. It says, “Hey, I can be part of the team, and the team wants casual Friday. But I’m still here to get the job done, to be a professional.”

There’s still some amount of judgment involved, and you may still have to practice the fake tuck method to make your decision on this crucial matter. You may want to bring in the opinion of an objective observer to help you make your final decision. Ask a friend or your spouse – or even your kids – about whether you should tuck on any particular occasion. It’ll be obvious to them, and if you’re lucky enough to have someone who’ll tell you the truth, you should definitely take their advice.