Whether you opt for crisp cotton or tailored silk, this timeless basic can pair with practically any bottom, from beat-up jeans to all-business trousers or even a silky, night-out skirt. What’s most important is choosing a fit that suits your figure (for tips, see Button-Down Shirts for Every Shape). Most body types look good in a slightly fitted style, like this tuxedo-inspired shirt with shape-enhancing darts and a cut that skims over the torso, not hugs.
Invest in cashmere if you can: The luxurious knit is seasonless, so it feels toasty in the fall and winter, yet isn’t suffocating over light dresses during warm months. (The cashmere cardigan here is made of a lightweight two-ply knit—thin enough for layering or summertime wear—and comes in eight colors.) For a less-costly runner-up, try a cotton-silk blend. Whatever the fabric, a V-neck is almost universally flattering and won’t run the risk of looking dated, so long as you stick to a neutral such as black, navy, gray, or ivory.
Leave it to the French to recognize a true style stalwart (see 19th-century French sailors, mid-century Paris café patrons, and current-day fashion designer Jean Paul Gaultier). Paired with cutoffs in the summer or peeking out from under cozy cardigans and jackets in the winter, this striped top offers a nice punch of color and a pattern that will never go out of style. Best color combos to try: navy stripes on white, white stripes on navy, red stripes on white, or black stripes on white. A fashion insiders’ favorite, the tee shown here is the real deal—it was created in Normandy in 1889.
It’s not as stifling as a turtleneck—or as unflattering (and boring) as a crewneck. Select one in a knit that’s lightweight and not-too-clingy, so it has a body-skimming drape and can be worn year-round. Try cotton, wool, rayon, or silk blends in a cheery jewel tone or a hardworking neutral. This emerald green pullover has elbow-length dolman-type sleeves for even more seasonless wearability (it also comes in black).
You can rest assured that a flowery print won’t go out of fashion anytime soon, since florals seem to be a “new” trend on runways annually. For the most versatile version, choose a soft, feminine top that hits around the hip bone; you’ll have the option of tucking it into tailored skirts and trousers for work or dressy occasions, or letting it hang loose over jeans for more casual outings. A beautiful silk blouse with peasant sleeves and pin-tucking details makes a nice pick.