Can I Dress Both Conservatively and Stylishly as a Young Person?

Can you dress conservatively as a young person and still be stylish? I won’t wear anything strapless or backless — or really any style where I won’t be able to wear a normal bra. That means ruling out a lot of dresses that are currently on trend. Is it wrong (or just cringey) to have these rules in the first place? Do I need to show more skin to be fashionable, or is it OK to be covered up? — Jessica, Denver

It’s true that “conservative,” at least when it comes to style, is often treated as something of a code word, or even a synonym, for “boring.” And the naked look has proved astonishingly resilient, not just on the red carpet and during award show after-parties, but also during urban summers everywhere, for a variety of reasons. And that tends to get a lot of attention because — shocking! (At this point, not really.)

But it’s also true that we live in an era in which all trends exist at all times, and it is more than possible to be covered and chic and contemporary all at once. And not just thanks to “modest fashion,” the giant market segment that officially emerged in the early part of the 21st century.

That’s when labels like Alessandra Rich and etail sites like the Modist were born. Though modest fashion is often associated with religious dictums, it is so much a part of life that it barely gets broken out as “modest” any more. After all, a great trouser suit has you covered as well as any caftan. Even TikTok, which can seems like the home of the dress that looks like a handkerchief, has almost 800,000 posts devoted to the hashtag.

If you are looking for a role model, however, consider Carolyn Bessette Kennedy, the style-setting wife of John F. Kennedy Jr. Before her tragic death in 1999, she often wore high-neck, long-sleeve, below-the-knee outfits (albeit by Yohji Yamamoto) and pretty much exemplified the allure of keeping things private. Or, for that matter, Catherine, Princess of Wales, who — thanks to the dress codes that still govern the behavior of the royal family — rarely shows much skin, yet manages to be highly stylish.

Or, for more inspiration, “try looking outside the U.S.,” said Sarah Miyazawa LaFleur, a founder of the M.M. LaFleur label. “You’ll rarely see a bare shoulder in my native city of Tokyo, even when it’s 100 degrees out, but Japanese women always find a way to have fun with fashion.”

As for how to start building such a wardrobe, Ms. LaFleur and Karla Welch, the stylist who works with Tracee Ellis Ross and Eve Hewson, suggested starting with a great blazer, which can hide a multitude of cutouts. Ikram Goldman, the owner of the Ikram boutique in Chicago, would add a three-quarter-sleeve crew-neck dress or an empire-waist dress. And, Ms. Welch added, a wardrobe of sheer tights is always a useful hack.

The point is, the only dressing rule that is really still inviolate is that you should feel comfortable and confident in your clothing, and if that means being covered up, there’s nothing cringey about it.

What’s cringey (and misguided) is wearing something because it’s what you think the crowd is telling you to wear. That’s the definition of fashion victim, and no one wants to be that. Indeed, perhaps the best way to think about your version of “conservative” fashion is as “personal style.” Doesn’t everyone want that?

Your Style Questions, Answered

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.