Years ago (the date on this article, actually, I back-dated it), I wrote an old comment that I thought—still think—was insightful. So I touched it up and put it together here, for you. Enjoy!

This advice might be easier or harder to follow than you're expecting. For convenience, I've broken things down into four sections.

1. Color
2. Styling
3. Quality and Details
4. Holism

Color

Michael Hill's eye for color is, as far as I can tell, unmatched. Every piece from Drake's is juuuust the right shade for me. I think you need that kind of skill to design a decent tie, which Drake's does exceptionally well, but it extends to all of their garments and accessories.

• Their complex accessories -- patterned ties and scarves -- are really great, and this is a key reason.
• I got a reversible khaki/olive games jacket with a navy stripe on the olive side. You think of all those colors as neutrals, but they really were each a beautiful shade. Khaki can be boring, olive can be pukish, navy can be bland, but they each stood out to me as just right.
• For that matter, my burgundy chore coat -- certainly not a neutral -- feels pretty neutral, and looks good in a wide variety of pairings.
• And this extends to their lookbooks. They pair and layer rich colors and pastels so well that they feel loud and subdued at the same time, in the best ways.
• And there's your first challenge: unless you have a wardrobe full of Drake's and try to match their lookbook pairings, you're just going to need to train your eye for color to do what they can do. I'd recommend you start getting a couple of pieces here and there where the colors really speak to you, and play with them. Don't settle for "olive" -- pick the exact shade of olive that makes your heart happy.

Styling

Drake's styling is better than any individual piece. I love Drake's pieces, but, again, the way they combine colors and the way they layer is really just... masterful.

• This is good news in that you don't need to splurge on Drake's pieces to style your clothing well.
• This is bad news in that you can't just buy their clothes and be well dressed, you actually need to learn how to style things like them.
• You can't just buy all their stuff and copy their styling. It sounds like it should work, but it doesn't. Maybe they don't fit on you the way they fit on the models, maybe there's a problem with lighting or skin tone, but it really won't be that great. You need to train your own eye to do it independently for your context.
• Part of this was forged in the fires of 2010s tumblr; that wave of sprezzatura culture is where you get, for example, the OCBDs with the unbuttoned collars. A lot of people learned from each other over time. Develop your taste by finding cultures you want to learn from, immersing yourself in those cultures, and trying to see what makes them good.

Quality and Details

Buy good clothes. Don't settle. Drake's clearly charges a design premium on most pieces. Their clothes cost more than they "should" in the sense of quality. But they're quality clothes, and they have key details. The drape of each fabric is intentional. The pocket positions are intentional. You're going to struggle to replicate that effect with cheap pieces you get from Abercrombie and Fitch. They can be styled well, of course, but quality and details do matter.

• You can find some of the companies that make Drake's clothing. As one of their more open secrets, most of their crepe-soled shoes liek the Crosby chukka are made by Astorflex. However, the Crosby is a style that you can't buy from Astorflex. It's a little quirkier. A little uglier—which, as I discuss below, can be a good thing. It's a chukka boot with an apron. It flattens out in interesting ways. Is that a pro or a con? Are you willing to pay extra for Drake's model over an Astorflex model? Is the Astorflex model really "good enough" as a substitute, or are you missing the point?
• Don't settle for something that's high quality but has the wrong details. If you love the jacket except you hate the lapels, don't get it. If you love the pants except you hate the pockets, don't get it.
• Don't settle for something with the right details and color if it's made from cheap material that won't drape right, or won't age right. A wide lapel is great because it puts more fabric up front , shows the way the fabric rolls over itself... There's a reason we spend money on expensive materials.
• There are exceptions to the value rule. Drake's makes its own shirts, ties, scarves, and pocket squares. If you're buying in GBP, these prices are... not competitive, but not too inflated.

Holism

Try to think holistically. Individual pieces that look ugly at first can come together in beautiful ways.

• Drake's does this, in part with ugly shoes. I write about ugly shoes here.
• Drake's also uses tweeds and bellows pockets and a lot of cotton suiting, which I'm generally not a fan of, but combines them in ways that I can appreciate.
• Always think, "what am I going to wear with this?" Maybe you don't have the piece yet, but can you see it in your minds eye? Don't fetishize the individual object, understand where it fits into a complex outfit or a complex wardrobe.
• Take some chances, buy some things that seem a little outlandish but really interesting, as long as you think they fit your vision. I don't mean to settle—rather, I mean to experiment. Notice the details, and instead of saying, "well, I don't like that, but I'll get it anyway," say "I like that. I'm not sure why, I'm not sure how, but I know I like it, I will make it work"—yeah, do that, go for it. Then, try to figure out why it worked, or why it didn't, after the fact.
• The photography is part of what makes all of this good. I'm not going to teach you how to take. a photo this good, or how to transform yourself into Jason Jules. Only Jason Jules gets to be Jason Jules. But you can still dress well.

See also

• Ben dresses like he belongs in a Drake's lookbook
• A few hundred more photos of Drake's inspo.
• Drake's Editorials, in case you haven't had enough.