Of all the styles a man can choose, this is the one I see getting the most discussion. Most of it comes from a pretty simple question. ” Is it appropriate to wear a suit jacket with jeans.”

The answer is (as always) that it depends.

Most arguments you hear against it come from three different camps:

Why wear that combo instead of a suit?

Why wear a jacket when you’re clearly going for comfort by throwing on jeans?

How are you doing it to actually make it look good?

So let’s dive in and approach the issue from all three angles.

While most men will err on the side of casual comfort, there is a growing contingent of guys who have taken things in the opposite direction. These are the Barney Stinson’s of the world who won’t set foot outside their door without a suit.

I can sympathize with this mentality. When you’re trying to separate yourself from the average Joe’s in the world, the quickest and easiest way to do so is with your clothing. Working out takes time to see results, you can’t change how tall or handsome you are, but you can get a well-fitting suit within a matter of weeks.

The problem with the “Suit Up!” mantra is - when the only tool you have on your belt is a hammer, everything starts to look like a nail.

I focus a lot on this site about the difference between dressing appropriately and dressing well. Most men know how to dress appropriately but don’t know how to dress well. However, those who say you shouldn’t be out in public unless you’re dressed to the nines are making the opposite mistake – they may be dressed well, but they’re not appropriately. A man’s wardrobe is a toolbox just like the one he has in his garage and each item of clothing is an individual tool. Don’t let your suit become your sartorial version of WD-40 and duct tape. It may hold everything together, but using the right tools for the right job guarantees a better result. And a man’s goal is to always get the best results.

The next argument is that it’s silly to throw on a jacket when you’re clearly casual and comfort-focused by wearing jeans.

If you’re reading this site I hope by now you know that dressing well does not mean dressing uncomfortably. I may not be able to play a game of pickup football as well in my sportcoats as without, but having them fit me properly means I can go through a normal day just as comfortably with a jacket as I can without.

In fact, I’m actually more comfortable with my jacket on. I hate having things in my pants pockets and I don’t want my phone too close to the boys. Rather than carrying around some wimpy satchel or bulky daybag all day, wearing a blazer means I have the extra pocket space I need for my phone, a comb, a pen, my business card holder, and whatever else I need to carry. It also makes me feel safer because it makes concealing a weapon easier – and there’s nothing more comfortable than safety.

Lastly, the right kind of jacket can be appropriately casual. I won’t be wearing one to the beach, but I’ll still be the best-dressed man in the room without looking like I don’t belong there. You can’t own a room if you’re out of place.

The last, and most difficult question is how to pull this look off appropriately.

Here’s where the “depends” answer from the first question comes in. You can’t wear a suit jacket with jeans if it looks too obviously like it belongs to a suit, and 99% of the time this means no suit jackets at all.

Instead you’ll want to wear a sport coat or blazer to pull this look off.

Here are a few other key things:

• As always, fit is king. If your clothing doesn’t fit you’ll look like Jerry Seinfeld instead of the High/Low man you want to be.
• You need slim or slim-straight jeans. Even if you’re a big guy, you want jeans that aren’t too baggy. You also want dark jeans unless you’re in the middle of summer.
• Wear the right shoes. That may mean dress shoes or chucks, just no athletic shoes.
• Know which shirts should be tucked in and which shouldn’t.
• Single-vented jackets are easier to pull of than dual but dual vents are still possible.
• Single-breasted jackets are easier to pull of than double but double-breasted are still possible.
• Two-button jackets only. Arguably you could get away with a 3/2 roll , but anything else is going to be too formal
• Notch lapels trump peak lapels.
• NEVER ever wear a jacket with pin stripes. While most patterns are more casual than solids, the pinstripe has a business-suit connotation that too obviously makes it look like you’re wearing a suit jacket instead of a blazer.
• Unless it’s after dark or the rest of your clothing meets the monochrome rocker look, black is a terrible choice. It’s too formal a color and will have the same effect as pinstripes.
• A shorter jacket will look more casual. This doesn’t mean it has to be trendy short, but one that’s too long will look awful.
• The less lining the jacket has the better. It will mold more to your natural body structure and look better in a casual situation
• No or very minimal shoulder padding. You should be doing this anyway, but a natural shoulder looks best on jackets.
• Ticket pockets are more formal. It’s still possible to make a jacket with a ticket pocket look good, but it’s more difficult.
• Flatter materials are better than those with more sheen. Think of tweed vs velvet and how easily the former and difficult the latter are to wear with jeans.

Now that you know the difference, it’s pretty easy to see why these two pictures:

Look so much worse than these two:

The above stuff may seem like a lot of rules, but what they essentially do is break down a formal item into more casual version. By default the jacket is going to be the High with your jeans being the Low so dressing up your jeans (dark, slim) and dressing down your jacket (everything else) will bridge the gap between the two and make the overall look more consistent.