I own approximately 47 pairs of jeans. I counted. And yet some mornings I stand in front of my closet genuinely convinced I have nothing to wear, which is either a personality flaw or proof that owning more stuff does not automatically make getting dressed easier. The real issue isn’t the number of jeans — it’s not knowing how to wear denim in more than one way. The same pair, the same combination, the same result every time.
Here is the thing most style advice skips over: the jeans themselves are maybe 40% of any outfit. The other 60% is what you put with them — the shoe that changes the whole energy, the belt that makes a basic top feel considered, the bag that sets the tone before you even walk in the door. Once you understand that, every pair you already own starts to look like five different outfits.
Why Relaxed Fits Actually Work
Relaxed-fit jeans are not the baggy jeans of 2003. That distinction matters. These are structured enough to look intentional, loose enough to feel comfortable on a real human body, and — this is the part that still surprises me — genuinely flattering across a wide range of body types in a way that straight-leg and skinny cuts simply are not. The trick that nobody talks about is contrast: you need something that anchors the silhouette, or the whole look reads as shapeless. A fitted tank tucked in at the front. A sleek blazer. Literally anything that creates a defined point somewhere in the outfit. I tried pairing mine with an oversized crewneck once, convinced it would look cool, and I looked like I was wearing my older brother’s clothes in the worst possible way. A belt fixed it immediately — which brings me back to the 40/60 principle.
Kendall’s been photographed in relaxed denim with pointed-toe heels and a tucked white tank roughly a hundred times, and the reason it keeps working is simple geometry: the volume of the wide leg against the sharpness of the pointed toe creates visual interest without any effort. You do not need a stylist to replicate this. You need the jeans, a white tank, and any heel or pointed flat you already own. The oversized button-up version works too — leave it unbuttoned over a fitted tank, tuck the front hem in, leave the back out, add a belt. The jeans do the heavy lifting and the shirt just floats.
And then there is the sneaker version, which is arguably the most-copied look right now.
Relaxed jeans, white leather sneakers, oversized sweater. It looks effortless because it is effortless. That is the whole point.
Dark Wash: Still the Most Useful Thing in Your Closet
Dark wash denim photographs beautifully, hides everything, and somehow functions equally well for a 7am coffee run and a last-minute meeting you forgot about until 8:55. It never stopped being relevant — it just got less rigid about how it’s supposed to be worn. You’re seeing it now with ballet flats, combat boots, silk slip dresses worn over the top, leather jackets, structured coats. The dark wash is the blank canvas; whatever you put with it does the talking, which is either liberating or paralyzing depending on your relationship with decision-making.
The formula I keep coming back to is dark denim with a soft, fluid top — a silk camisole, a delicate blouse, something with movement. The contrast between the structured weight of dark denim and the lightness of a flowing fabric creates a tension that feels genuinely modern without requiring you to buy anything new or particularly expensive. Add a leather belt and a structured bag and it reads as both relaxed and put-together simultaneously, which is the goal of most outfits if we’re being honest. The dark-denim-and-leather-jacket combination has been done so many times it almost feels like a cliché, but it keeps getting done because it keeps working — the only real variable is finding a leather jacket that actually fits your body rather than grabbing whatever’s on sale in your size.
White Jeans Aren’t Actually That Precious
They just require you to think about the rest of the outfit, which, honestly, you should be doing anyway. White and ecru jeans act as a neutral base that lets everything else do the work — a rust-colored sweater, a sage-green button-up, a butter-yellow camisole all pop against white denim in a way they simply do not against blue. Gigi has been wearing crisp white jeans with oversized blazers, tiny cropped tops, and basically everything else in her wardrobe, and the consistent thread is that the jeans are always clearly intentional. They’re pressed. They fit well. They’re not an afterthought.
The striped shirt and blazer combination is the reliable entry point here — not original, but genuinely timeless in a way that earns the word. It works for brunch, for the office, for a casual dinner. What makes it feel current rather than default is the shoe choice: white sneakers keep it relaxed and modern, heels move it into elevated territory, loafers split the difference in a way that feels very right now.
Actually, that is not quite right — loafers do not just split the difference, they shift the whole vibe toward something more intentional and slightly fashion-forward, which is a meaningful distinction if you care about that kind of thing.
Ecru jeans are worth separating out because they function slightly differently. Warmer in tone, more forgiving on stains, and somehow more sophisticated in a way that is hard to articulate. They are the better vehicle for tonal dressing — cream knit, camel blazer, chocolate-brown leather jacket — because the warmth in the fabric reads as a considered choice rather than a default to white.
Can You Actually Pull Off Double Denim?
Yes. The rule is contrast and the rule is non-negotiable. A light-wash jacket over dark jeans works because your eye immediately registers something intentional — two different things happening, clearly on purpose. A crisp white denim shirt-jacket over relaxed medium-wash jeans works for the same reason. What does not work is matching the exact same wash top and bottom unless you are fully committing to the editorial version of this look, in which case you need to lean into it hard: statement shoe, bold belt, something that makes clear this was a deliberate choice and not a laundry-day accident. The 90s denim vest over a fitted turtleneck and dark jeans is having a genuine moment right now — it layers well, it creates silhouette, and it has that specific nostalgic energy that is everywhere without feeling costumey.
Shoes Change Everything. Everything.
Boots with jeans is a completely different outfit than sandals with jeans. Loafers read differently than mules. Ballet flats have a different energy than pointed-toe flats, even though both are flat and both are shoes and they look nearly identical on a hanger. This is not a small distinction — the shoe is often what determines whether an outfit reads as casual, polished, downtown, uptown, weekend, or workday. I have worn the same dark jeans and white shirt combination with white sneakers (felt like a Saturday), pointed-toe heels (felt like I had somewhere to be), and knee-high boots (felt like a different person entirely). Same jeans. Same shirt. Three different outfits.
Jewelry works the same way, just more subtly. A simple gold necklace with dark denim and a white shirt feels clean and minimal. The same outfit with a chunky chain feels downtown and deliberate. Stacked rings, statement earrings, a single delicate bracelet — these inject personality into a combination that might otherwise feel like a uniform. With denim as your base, which is about as neutral as it gets, the accessories are where your actual style shows up.
There is no secret formula here. The celebrities you’re referencing aren’t doing anything you can’t do — they’re choosing jeans that fit, pairing them with pieces that make sense together, and committing to the choice without second-guessing it. That last part is probably the hardest part, and it has nothing to do with what you own.
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Frequently Asked Questions
What is the easiest way to make jeans look more intentional?
Add a belt. Seriously, that’s it. A wide leather belt or even a simple chain belt instantly makes a basic jeans-and-top combo look like you thought about it. It defines your waist and gives the outfit a focal point without requiring you to buy anything new.
Can you still wear skinny jeans in 2024?
Yes. They’re less aggressively tight than they were in 2015, but dark skinny jeans styled with an oversized blazer and pointed heels is still a genuinely good formula. The key is fit — they should feel comfortable, not restrictive.
How do you pull off double denim without looking like a mistake?
Contrast. Always contrast. A light-wash denim jacket over dark jeans works because your eye immediately registers that something intentional is happening. Matching the exact same wash top and bottom reads as an accident unless you’re going full editorial and committing hard to the bit.
Are white jeans difficult to style?
They’re actually easier than people think, but they do demand more attention to the rest of your outfit. White jeans act as a neutral base, which means a colorful top or a bold shoe will do a lot of the work for you. The classic striped shirt and blazer combo is a reliable starting point.
What shoes work best with relaxed-fit jeans?
Pointed-toe heels or flats create the best contrast against the volume of relaxed jeans — the sharpness of the toe balances the looseness of the leg. White leather sneakers with an oversized sweater also work well. The one style that tends to fall flat is a chunky platform, which can make the whole silhouette feel heavy.
