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Dress shirts are a staple of every man’s wardrobe, regardless of their age, profession or style – and these days, a man’s dress shirt has become as adaptable to different settings as a dress is for a woman. As an avid traveller with a penchant for over-packing, I will always pack an extra one or two dress shirts over any other type of shirt. And on those trips where excess baggage is not an option, be confident that no matter what you pair it with, be it a pair of jeans, khakis, dress pants or even shorts, it will make its mark. Here, then, are some rules you should follow when deciding how to dress down your dress shirt.

To tuck or not to tuck?

That is indeed the question. It might seem like an easy choice, but it actually isn’t, and you should think about it before actually making the choice. There are some clues to help you when making the decision. If the shirt hem is even, it is generally left untucked, but the majority of dress shirts are uneven, so the rule of thumb is making sure the length of the shirt doesn’t go below the middle of your back pocket.

Beyond this, think about where you are going when you make the decision. Is it casual? Will a tucked in shirt help you stand out? Be aware that your waist does matter. If you are carrying a little bit more weight in your midsection, keeping a shirt untucked actually might cause the opposite reaction. The fabric of the shirt matters here, so be aware of its sheerness and thickness — what exactly are you showing off? Of course, if you are doing layers, please tuck in your shirt. An untucked shirt with a jacket only works on the ramp. Also, never untuck the dress shirt you’ve tucked in. It will create a sloppy look, and that’s not a message you want to send, unless you are running around bussing tables at a fancy restaurant.

Pop the collar

A polo shirt? On occasion. Coats and blazers with lapels? It could work. A dress shirt? Absolutely not — end of discussion. You aren’t Diane Keaton.

Loosen up the buttons

Unless you are a rock star, buttons matter. First figure out what the distance is between your buttons. Then understand the fit of the shirt — if it’s a slim-fit, chances are the buttons are closer together. While the top collar button is left open, if the second button is bunching up and causing the shirt to look pulled on, keep the second button open too. This look will work regardless of the season. You shouldn’t ever be putting your undershirt or nipples on display, and if you have a forest growing on your chest, be careful about how much of it you want to share with the public.

Get sleevy

Let’s get this out of the way — a poorly sleeved-up dress shirt can kill an entire look. It can also ruin a well-tailored shirt permanently — so here are the basics.

If you are wearing a blazer or suit and wish to hide the cuff, do so inside, before wearing the jacket. A rolled up jacket just doesn’t work (unless it’s a denim jacket, and with that too, one fold is enough).

If you need to roll them up to wash your hands, great. Don’t forget to roll them back down.

If it’s hot outside, fold the shirt as and when needed. Again, fold back once you are back in the AC.

If you are doing it for the “look”, which most guys think they are (but they are actually doing it for the previous two reasons), then here are the two ways to do it properly.

„ The forearm length: Unbutton the cuff and gauntlet buttons. Flip the cuff back and turn it inside out. Fold over once, hiding the cuff behind the sleeve fabric. Tuck in the corners of the cuff, and there you have it. The benefit of this untuck is that generally, this will leave the least amount of creases on the shirt.

„ The elbow length: Follow the first two steps, but instead pull the flipped cuff all the way to just below your elbow, turning the sleeve inside out. Then take the bottom of the inside-out portion and fold it up, till it encompasses the bottom of the cuff. You then decide how much of the cuff you wish to show. Many dress shirts have a contrasting lining, so this looks particularly smart when dressing down.

As a rule, the wrist is normally all that’s needed to be sleeved up till. Remember, the bulkier the roll looks, the more attention your arms are getting, so be sure the sleeves are rolled/folded properly and are the same length on both arms.

Finally

„ As a rule, white, pink and blue should be the staple plain coloured dress shirts you should travel with. One checked and one oxford blue stripe shirt would be ideal additions.

„ If you are wearing a T-shirt and layer it with a formal dress shirt, you are going to be categorised as a lazy dad aka Ray Romano.

„ Iron your dress shirt even if you are wearing it casually. Let the wear and tear make it casual. Without ironing, it won’t look effortless, just unwashed.

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