Hey Tyler - love love love this question. Thanks for asking. If you've been reading this column for a while, it probably won't surprise you that I don't mind breaking a rule here and there. Nothing crazy – I wear a tie six days a week – but for me, white jeans are a year-round thing. So there's no better time to answer this question than right before Labor Day.
So you've already taken the first step in buying a pair. (Thank you, by the way.) The next one – wearing them out of the house – might seem intimidating, but once you've got a system dialed in, I find white jeans as versatile as blue jeans, and in fact many times more. And it doesn't matter which kind of white jeans... our version or Levi's or selvedge or even white 5-pocket cords in a 14-wale corduroy. I love 'em all, wear 'em all, and keep 'em stocked in our shops. Hopefully you'll discover they work with a bunch of stuff that's already in your closet... and certainly don't deserve to be relegated to the bench for 9 months out of the year!
In terms of some basic outfits - here's a three-rule formula to get you going:
Rule No. 1 - Focus on two types of shoes and match your belt to them. I think white jeans look killer with either dress shoes and no socks (tassel loafers, penny loafers, bluchers, double monks), or boots (Chelseas are especially good, and obviously so are socks in this instance). And from there just match your belt to your shoes in general color and texture. Don't overthink it, basic rules apply - brownish to brownish is great, or you can be a little more on the nose, like hooking up your sharkskin tassels with a sharkskin belt.
Rule No. 2 - Wear a little pattern up top and don't be afraid to throw on a jacket. Since white is a bold solid (it can tend to sing lead,) I like to offset that with a little pattern in my shirt or jacket. Shirt-wise, I go for quiet patterns in softer, more subtle color tones, usually light blue or pale pink. Small bengal stripes, pencil stripes, and small graph checks are all easy options and look great under a solid navy, green, or even a brown blazer.
Now if you've got a jacket with a little pattern to it - say a herringbone or houndstooth or even a bolder plaid - those work beautifully with white jeans. I'd just consider dialing the shirt down to a solid color rather than a pattern, to let that jacket shine. And no matter the jacket, a navy knit tie will always punch it up just a bit.
And as the weather turns cooler, I love adding outerwear to the mix. A military jacket in fall fabrics (moleskin, flannel or corduroy) and fall colors (olive, navy, even camo) looks SUPER cool with white jeans, and speaks to the changing of the season. We just did a fall photoshoot for our pals at Hodinkee, and paired our watercolor camouflage military jacket with white cords, graph check shirt & light blue sweater. But any kind of casual jacket will make white jeans feel intentional and autumnal.
Rule No. 3 - it's okay to break the rules. These aren't set in stone. A solid color polo or chambray shirt will look cool with white jeans on a warm September day, and a navy cashmere crewneck can look super chic paired with white jeans in the wintertime... and there are a ton more examples like that once you find your white jeans groove. But while you're starting out, if you stick to the first two for the first few wears, I think you'll be feeling confident in no time.
Hopefully these get you on your way... thanks again for writing in.