Surprisingly Simple: How Stylish People Tackle Transitional-Season Dressing
From Kendall Jenner to Hailey Bieber, I wondered how they dress on spring days that swing from cold to warm.
The reason transitional-season styling is difficult isn't because it's cold or because it's hot. It's because the weather sits somewhere squarely in between. Think of an ambiguously awkward April morning. Pulling out a heavy coat feels excessive, yet heading out in just a T-shirt feels daunting. The sun can be fairly warm during the day, but mornings and evenings still bring the reality of cold hands and feet. And having to agonize over what to wear every day is just tiresome.
So how do the people who dress best right now solve this problem? From Kendall Jenner to Kaia Gerber to Hailey Bieber. Looking into the answers they've found, the first thought is that, as expected, it's oddly simple. One item you can layer, a silhouette you can wear comfortably all day, and an accessory that fine-tunes those small differences. Remembering just this is enough. Refer to the five looks below that can be used from the morning chill to the midday sun to the cooling evening.
Throw on a Sports Jersey or a Varsity Jumper
Hailey Bieber's answer was a leather bomber jacket with a New York Knicks patch. Paired with baggy pants and a mini leather bag, it's sporty yet clean. The key is that one jacket wards off the morning chill, then can be shrugged off easily under the midday sun. You could apply this with a jersey of your favorite team or a stadium jumper, too.
Pair Well-Chosen Basic Items
Even Kaia Gerber, who can look flashy, often wears basic looks. At first glance it seems she picked them up without thought, but when you try to copy it, it's surprisingly not easy. The reason basics are truly difficult is that a single mistake shows immediately. A denim jacket that fits perfectly without excess, proportions modestly completed with flat shoes, and a graphic T-shirt and baseball cap that stand out effortlessly anywhere! Tonight you could prepare for the week with Kaia-style basic matching.
Wear Wide-Fit Jeans
If I had to pick one ultimate item for the transitional season without hesitation, I'd choose jeans. This season I especially recommend a wide-leg fit. It lengthens the silhouette while remaining comfortable, so it's good to wear all day. If you throw on a thin, colorful spring jacket like Emily Ratajkowski, you won't be thrown off by the fickle temperatures.
Use Neutral Tones and Asymmetrical Cuts
It's hard to define Kendall Jenner's look in one word. The The Row coat look, with a subtly mint-green palette topped with an asymmetrical cape, was the same case. It's quiet but eye-catching, simple but not boring. When wearing neutral tones, the point is to compete with silhouette rather than color. Even the same beige and cream tones become light and finally fit for spring the moment the cut changes. As Kendall always proves, she communicates through shape instead of relying on color.
Carry Your Bag in Front
The trick Lila Moss showed was none other than the 'way of carrying a bag.' A black coat with a gray knit and denim, and then slipping a vintage-mood bag over the forearm. It doesn't matter if it's new or a bag you've had for years. What matters is where and how you carry it. Held in your hand it's just a bag, but tucked over the arm it becomes an accessory that keeps you worry-free even in the layered-up transitional season. It's the simplest yet most certain finishing touch.
Published: April 1, 2026
