When people ask how I would describe my style, I tend to say things like “timeless,” “classic,” and “simple with an edge.” If I’m asked what kind of shopper I am, I respond with phrases like “not a trend follower,” “investment value shopper,” and “instinctive.” Scanning my closet, my self-reflection is confirmed as I gaze at pieces I’ve collected over the past couple of decades— lovingly curated so that items that are now considered vintage hang happily next to my latest purchases.

As we pivot to the new decade ahead, I wonder which styles will persevere through the 2020s and beyond, smoothly riding out the next ten years alongside whatever trends may pop in and out. Here are my predictions—and suggestions—of what you can safely invest in now and wear past 2029.

White: Both the Color and Clothing

I’m stating the obvious when I say that white t-shirts are a forever fashion staple. (James Dean, anyone?) Finding “the right” white t-shirt—and keeping it fresh looking, however, can also be a forever challenge. I get around the white t-shirt dilemma by stocking a rotation of less expensive basics and peppering in some higher-quality, higher-design ones that I wear less often.

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For basics, keep an eye on fast fashion retailers like Brandy Melville and Urban Outfitters, midscale ones like ATM, Maje, Re/Done and Vince, and check out subscription based retailers like For Days.¹

The quest for a great white shirt isn’t limited to tees. A crisp, white woven, winter white sweater or perfect white jean can be equally vexing to find. To the extent that your budget and patience allow, I suggest you take some chances when choosing white clothing. Because the palate is literally blank, white tops and bottoms can push the envelope in terms of detail and design because an extra pleat or fold here or a funky stitch detail there aren’t as obvious as they could be on darker clothing. So go ahead and get that deconstructed white shirt or invest in a cool men’s white woven. You’ll stand out just enough and feel bold inside without feeling self-conscious.

Finally, no talk of white would be complete without the white wardrobe staple MVP: the white shoe. Sneaker, sandal, pump or boot, there is nothing that brings freshness and a twist to outfits like a white shoe. Thankfully, the white shoe has finally been unshackled from its seasonal confinement and finding gorgeous styles to wear all year round has become much easier. The biggest challenges you’ll have with a white shoe is keeping the heels and toes protected and pristine...and also keeping yourself from buying too many!

Jeans of Any Type

Like its kissing cousin, the white shirt, jeans are never out of fashion. Yes, some jean styles can fall from grace but chances are 1) they’ll be replaced with new styles or 2) they’ll make their way back en vogue, just give it time. I find it difficult to get rid of jeans. I never know what fit I’m going to need or want at a given time. To compound my issue with “too many jeans,” I find it hard to pass up a pair that looks and feels fantastic, even as my teenage daughter's voice rings in my head, “Mom, those look like every other pair of jeans you own!” So go ahead and accumulate. Recycle or repair your oldies but goodies, ensure a good assortment of dark and light denim washes, cropped and full leg styles and relaxed and more tapered fits, and always allow yourself the option to save that favorite pair in a keepsake box or storage bin. The Levi’s “Two-Low” jeans I wore throughout both my pregnancies will always have a place in my heart’s closet.

Boots that were made for walking...or standing...or dancing…

Living in the San Francisco Bay Area where the weather never wildly varies, I’ve become a seasonally agnostic shopper. While I wear white year round and am not embarrassed to wear sandals when it’s 70 degrees in January, I do keep one shopping practice holy: The Fall Boot Purchase. I could be lazing on a pool float or heading to dinner in a sundress, but if it’s late August, my mind is on boots not summer breezes. Needless-to-say, I’ve amassed a nice collection of boots over the years, rarely cycling through old pairs to make room for new ones.

Thinking about this blog post, I took a careful look at my boots, curious as to why I almost never consign older styles (recently, I even gravitated toward a pair of Riccardo Tisci for Givenchy snakeskin beauties from 2008 when shopping at Decades in Los Angeles.) Scanning my boots, I realized that each pair has its own set of uniquely stylized features—details like grommets and studs, fabrics ranging from patent leather to tweed to lurex, bright pink, green, purple and red proudly displayed alongside cool metallic shades of silver and gold. At that moment, it occurred to me—boots never go out of style. In fact, the more particular the boot’s details, the less dated and commonplace they seem. The lesson here? Grab the boots that catch your eye now. Chances are they’ll be a mainstay in your closet for years to come.

Designers with “collection value”

While it can be really tempting to shell out big bucks for the season’s “it” bag or shoe, I encourage you to stop and ask yourself this question: Where do you see that new, hot item next year and will it feel as special and exciting to you over time?

We’ve all been pulled into this swirl. Scroll through Instagram and you’ll swear your life won’t be the same without Bottega Veneta’s Pouch, Re/Done’s latest high waisted jean style or that cute but questionably practical microbag. My personal and professional words of wisdom: After some early passion, it’s likely that these kinds of purchases will start to feel less relevant and more ubiquitous pretty quickly. (Even Bottega’s Pouch, while absolutely gorgeous and available in an array of colors and fabrics, will feel like a commodity the more you see others carrying it.) Instead, focus your energy and hard earned dollars on designers like Rick Owens, Dries Van Noten and Mary Kate and Ashley Olsen of The Row, all legacy designers who create continuity across and build value into their collections. Furthermore, like a trusted friend, you can count on these designers to add just the right amount of newness to the styles and silhouettes they produce each season, while still staying true to their core aesthetic. In fact, the changes from collection to collection may be so subtle that the only thing you notice is an increase in the price year over year. So, my parting words to you are this—if you’re committed to a designer and you’re pondering if you should buy “that” iconic piece, do it. Leather leggings from The Row and Celine’s double faced cashmere coats will look pretty much the same today as they will in 2029. They’ll just cost you a whole lot more.

¹A company in which Jessica and her husband are small investors.