Some days, it just works. I throw something on. Glance in a full-length mirror. Done. Moving on.
Other days, it’s a negotiation. I put things on. Swap things out. Get frustrated that I didn’t get it right the first time. Spiral into a closet rage. Ask my wife for help.
Lately, though, I’ve found a workaround for when she’s not around. Color. It’s usually the last thing I think about. I’ll start with weather. Then proportions/vibe. Then I’ll put something on, look in the mirror, and only then ask, “Wait… do these colors even make sense together?” But when I flip that (and start with color first) everything else tends to fall into place. Fewer decisions. Less second-guessing. More first-try wins.
These are five combinations I keep coming back to in recent months.
Bone and Black
I once heard Fran Lebowitz describe something as “such a subtle shade of pearl gray that straight men think it’s white.” That’s exactly how I feel about these pants I just picked up from Imogene + Willie. I would call them white. But they’re not. More like… bone? Pair that with a black knit, like my current go-to from Son of a Tailor, and it always works. Every time.
Pro tip: Yes, this works both ways. But bone on bottom with black up top feels more intentional. Can’t explain it. Just does.
Navy and Cream
If you’re going lighter up top and darker on bottom, this is the one I keep defaulting to. A dark navy pant. My current pair is a selvedge full saddle situation from Buck Mason. Paired with something creamy and soft up top. Oatmeal, ecru, whatever you want to call it. I’ve been reaching for a Boast sweater that hits that tone perfectly.
It’s hard to mess this up. Feels classic without feeling predictable.
Pro tip: A chunky brown loafer with a red sock is a subtle way to wake the whole thing up.
Sky and Olive
This one happened by accident and stuck. I’ve got these heavily faded, borderline destroyed Levi’s I found at a vintage shop in Louisville. They’ve worn down into this perfect washed-out sky blue. I usually throw them on with an olive kimono jacket from Scotch & Soda that I’ve had forever. Something about the combination just feels right. Easy. Broken-in.
Pro Tip: Vintage military jacket is always a good option here, too.
Forest and Dijon
Green and gold has always worked for me. Especially when the yellow takes the lead. I’ve been wearing this mustard-y, almost dijon jacket from Signature Innovation Group that feels like it came straight out of the ’70s. Underneath, I’ll keep it grounded with a darker green tee. Madewell makes a solid one.
It’s an unexpected enough color combo to feel interesting without crossing into wtf territory.
Pro Tip: A dark green neckerchief also works.
Khaki and Baby
Khaki pants and a blue Oxford is about as classic as it gets. Which is probably why I tend to overlook it. Too obvious. But lately, I’ve been leaning into expected color combinations with slightly unexpected proportions. A boxy, slightly oversized blue button-up from Zara paired with a more tailored, pleated khaki pant from Todd Snyder.
It lands somewhere between dressed up and relaxed. Structured, but not stiff.
Pro Tip: If you’re going the traditional blue Oxford route, button the bottom two buttons of the shirt and messily tuck it in. And if you’re going the cropped boxy route, wear a high-rise pant.
