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She's Wearing WHAT???

The idea of appropriate office attire has changed dramatically.

The idea of appropriate office attire has changed dramatically — so we talked to four generations of women to hear what they think is OK to wear to work.

BABY BOOMER: Jane, independent school admissions. When I started working at our school 20 years ago, the headmaster required his assistant to wear a dress every day. That blew my mind. The world has become a lot more casual. You can be comfortable and still professional.

The women of my generation tend to be put together. We grew up looking to Audrey Hepburn and Jacqueline Kennedy for inspiration. We believe it’s worth investing in your wardrobe. When I wake up in the morning, I’m purposeful in planning out what I’m going to wear. I dress according to what’s on my schedule. Our headmaster once overheard me saying, ‘I need to wear a suit because I have to get a lot of work done today.’ It became a joke: if he saw that I wasn’t wearing a suit, he’d say that I must be slacking. I feel more professional when I’m dressing my best.

A 20-something-year-old teacher at our school wore tunics with low-cut backs that revealed tattoos. Another teacher had full sleeves of tattoos that she didn’t cover up. A colleague in her late 20s wore shirts with her bra straps hanging out — it was part of her look. We’ve had the cleavage conversation with some employees. Where do you draw the line? It may sound old school, but I’m waiting for the pendulum to swing in the other direction again.

GEN Xer: Dorotheen, corporate marketing. I’ve always thought that if you want to move up the corporate ladder, you should dress professionally. You feel more confident when you are in a power outfit. When you take care of yourself and think about what you’re wearing, you represent your company well.

My last company had stodgy rules when I started there. My boss once sent me home because I wasn’t wearing pantyhose. The employee handbook mandated that we couldn’t wear open-toe shoes. That floored me, especially in the summer when we were making sales calls in 95-degree heat. But I also thought things went too far the other way when that restriction was lifted and the younger women started wearing strappy shoes. They considered those sandals business casual. I considered them flip flops.

My favorite work outfit is a tailored skirt or pants in a solid color, a blouse with a splash of color, and heels: comfortable but still professional. I work with women who are a little older than me, and they seem to lose that creativity. The tailored fit goes away; they wear loose blouses and pants and comfortable shoes — and more browns and blacks. Women younger than me also wear less tailored clothes that look a little flimsy. They could wear a jacket with leggings, but the clothes are from a mall discount store. I also see younger women wearing what I’d call going-out clothes. I’ve attended meetings where some of my younger colleagues are wearing too-short skirts and too-low blouses. You need to think ahead when you’re getting dressed about who you’ll be interacting with and what they will think.

MILLENNIAL: Allison, brand public relations. When I started out in the corporate world, I thought I had to wear heels and conservative clothes every day. Then the athleisure trend took off and it became more acceptable to dress down. Blazers with leggings and athletic sneakers in place of flats were now acceptable at work. Then wearing “empowerment” T-shirts and similar items became a way to make a statement. That started in my generation and grew much larger among younger people.

Millennials have conformed to changing styles, but we still want to balance self-respect with respect from those around us. I wouldn’t wear an empowerment T-shirt with ripped jeans and sneakers, but I might wear it under a blazer with cute, non-ripped jeans.

You can see the difference between generations in hairstyles. Older women tend to be more coiffed and tame their hair with hairspray. For me, my hair doesn’t look well-washed some days or it’s up in a messy bun. I don’t own a shirt that says Messy hair don’t care, but that statement expresses my generation’s mentality. When I go to work with unwashed hair, people tell me it looks better! Now even that’s changing, with kids who’ve grown up on YouTube videos that teach them how to make side-braids and apply eyeshadow.

It seems like the older generation of women still follow old-style rules and wear what they think they should wear, like heels. Younger people have the attitude “I don’t care how people perceive me, I’m going to wear what I want because I know what I’m worth.” I’ve seen some Gen Z’ers dress in full-blown workout gear, which is so inappropriate and makes them appear younger than they are. I’ve also seen younger co-workers wear crop tops with high-waisted skirts or pants. It’s a great look, but they don’t think about whether it’s appropriate. Millennials care about both how we feel and how we are perceived.

GEN Z: Elena, intern in marketing and communications. During my last internship, I worked for a company that encouraged us to wear what felt comfortable and empowering. The office’s typical style was business casual, but we had wiggle room because we were working with on-trend creative people.

On my first day of work, I wore my mom’s hand-me-down suit and a button-up shirt. When I looked around, I realized I didn’t have to wear oxfords every day! After that, I dressed more casually. My favorite outfit was a pair of wide-legged, cropped trousers paired with a shiny green, fitted crew neck top, fun chunky earrings, and loafers. The unwritten rules were similar to your high school dress code: no skirts shorter than the spot where your fingertips touch, no spaghetti straps, ripped jeans, or cleavage.

I definitely noticed generational differences in how pulled together people looked. We had execs in their 40s and 50s come to work every day dressed flawlessly — truly like Mad Men-stylein dresses, refined jewelry, makeup, and heels. Their outfits said, ‘I earned this status and I demand attention.’ My manager wore pointed-toe stilettos every day, slacks or a pencil skirt, and a fitted sweater or button-up shirt. Many people reported to her, and her appearance mimicked control: her jewelry was sleek, her clothes were tailored, her makeup was impeccable.

No one my own age wore heels. We would wear trendy sneakers with dress pants and bold accessories, something I would never see a manager wearing. But some managers who were five or 10 years older than me, Millennials, did have a loose interpretation of business attire. I had one super tech-savvy manager who usually wore Birkenstocks, leggings, and a sweater. Another manager wore Vans, cool jeans, and funky sweaters. They all dressed in a style that was personal to them. They were confident. My biggest takeaway was that the women I worked with dressed in a way that empowered them.

Good news: Our bestsellers are always age-appropriate.

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