How to Look Stylish: Common Style Questions Answered

Ever put together an outfit you thought looked great - everything fit well, the pieces were on-trend - but something just felt off? You’re not sure whether to leave your shirt untucked or tuck it in. You love the look of a collared shirt under a sweater, but should all the buttons be done up?

These kinds of questions come up all the time. And the good news is, they’re simple to fix. Once you know the trick, you’ll wonder how you ever did it any other way.

Here are four of the most common style questions I get as a men's stylist, along with easy, practical how-tos to help you get it right every time.

How long should an untucked shirt be?

This is one of the most common style mistakes I see - a shirt that should be tucked in, or a stiff shirt that should be untucked, or a shirt that’s just the wrong size. 

A good rule of thumb? When you’re standing up straight, the bottom hem of your shirt should land roughly at the midpoint of your pant zipper. Any shorter, and it looks like you shrunk it in the wash. Any longer, and it starts to look oversized. 

You're better off staying away from shorter shirts and tucking in longer ones. A clean tuck gives you shape and purpose. And that’s the goal, right?

Can I wear a collared shirt under a sweater?

The classic collared-shirt-under-sweater combo is a common request. Seems simple enough, but there's a reason some guys pull it off effortlessly while others end up looking either stiff or a little sloppy.

The secret? It all starts with the collar.

When layering, make sure the collar flaps are tucked under the neckline of your sweater. Letting them sit on top gives the whole outfit a bit of a school-uniform feel. Not what we’re going for. 

Next, unbutton the top button on your shirt. It relaxes the look and makes it feel less buttoned-up (literally). You want this outfit to say, “I’m comfortable and pulled together,” not “I’m late for a board meeting I don’t want to attend.”

Bonus tips: Make sure the shirt underneath actually fits you well. If it’s too big or bulky, you’ll see the extra fabric bunching under your sweater. Tuck the shirt into your pants for a cleaner look, and if you want to add a little dimension, let the shirt cuffs peek out slightly at the sleeves. Small details make a big difference.

How do I wear a colourful shirt without it looking chaotic?

Wearing colour is a great way to add personality to your outfit, but balance is key. Pair a multi-colour top with solid colour pants that pull from the shirt itself. That’s the trick: choose one colour already in the shirt and match your bottoms to that.

Avoid throwing a bunch of unrelated colours into the mix, even if they’re neutrals. Yes, even black and white can feel like too much if they don’t fit the palette of your shirt. When you’re wearing a bold top, let it be the statement. The rest of your outfit should support it, not compete with it. A mismatched bottom can distract from the overall look instead of pulling it together.

What kind of patterns are most slimming?

Achieving a slimmer look doesn’t mean you have to rely solely on black or stick to vertical stripes.

What matters is pattern scale. Smaller patterns that are tightly spaced tend to be the most flattering. Think micro-checks, mini-dots, and subtle textures.

What you want to avoid are oversized prints or tiny patterns that are spaced too far apart. These can create visual noise that makes your frame appear broader. And remember, fit always comes first. A great pattern won’t work if the shirt is two sizes too big or too small.

For visuals of all these looks, head to my original Instagram post.

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