From Age 16 to 89, We Asked 33 Women for Their Life-Altering Style Wisdom

Personal style isn’t something you can just nail down early on in your life and call it a day. Cheesy as it may sound, finding a style that makes you feel like the best version of yourself, the most “you,” is more a journey than a final destination. Think about it: You’re a different person than you were a year ago, a week ago, and even a day ago, and the same can be said of how you express yourself through fashion. The clothes you pick out each day are a reflection of who you are on that particular day or point in your life, not a representation of who you are period.

With that in mind, we were curious to know what personal style looks like at every point in life. We asked the most stylish women we know to show us their outfits and share the most valuable nugget of style wisdom they’ve learned in all their years. From the 16-year-old who won’t pass up on a good shoe trend to the 88-year-old who’s a case study in classic style, read on to discover the best outfit tips for women by age, see what style at every decade looks like, and then shop pieces inspired by each woman’s style.

Her best piece of style advice: If you don’t feel good in what you are wearing, change your outfit. It can affect your entire day. How she describes her style: I like to mix simple silhouettes with edgy and unusual details. The one trend she’s keen on: Chunky-sole boots are so cool!

Her best piece of style advice: It is impossible to be stylish without confidence. How she describes her style: My style is a mix of high and low, vintage and contemporary pieces all while making it effortless and timeless. The one trend she’s keen on: Leather capris are on my radar.

Her best piece of style advice: I have become more minimal therefore, have started to build a quality wardrobe. It is also important to think about the environment and buy less. How she describes her style: Easy and effortless. The one trend she’s keen on: Maxi dresses. I am a petite girl and maxi lengths elongate my frame.

Her best piece of style advice: One piece of style advice I’ve learned is to be bold. My style is still forming right now because I’ve only recently gotten into fashion. I am trying to go out of my comfort zone and wear pieces in unique ways that reflect more to who I am rather than what everybody else is wearing. Basically, everyone at my high school went thrift shopping and were obsessed with vintage pieces, which motivated me to find unique pieces that speak to who I am! How she describes her style: My style is Portland vintage and skate style combined with more luxury petite pieces from brands like Reformation and Aritzia. The one trend she’s keen on: Pistachio. I am obsessed with this soft green color and I am itching to get a pair of pistachio pants or a blazer.

Her best piece of style advice: If a trend or article of clothing doesn’t feel right when you wear it, don’t. How she describes her style: My style definitely has a bit of a ’90s grunge spin to it with denim, tie-dye, pops of color, and statement-making accessories as the foundations. My best friend says that I dress like an angsty teen with an affinity for designer extras. The one trend she’s keen on: I am really loving the eighties resurgence—so neon, zebra print, and anything with a bit of that party vibe.

Her best piece of style advice: When in doubt, always wear an all-black outfit. It slims you and accentuates your figure. How she describes her style: My style is more on the classic and chic style. However, I tend to mix it up, so sometimes I find that my style is a bit more versatile. The one trend she’s keen on: Straw hats! I’ve been seeing them a lot lately. They’re perfect for the summer.

Her best piece of style advice: Stick to the classics—quality over quantity. How she describes her style: Chic, sophisticated, and classic. The one trend she’s keen on: Animal print

Her best piece of style advice: Stop wearing things you feel uncomfortable in to appease people. Your personal style is about you, and no one else. How she describes her style: A balance between sporty/comfort and avant-garde weird-ness if that makes any sense! The one trend she’s keen on: Every shade of green.

Her best piece of style advice: Mix clothes from affordable stores with something from designers. This way you can create something truly unique. The key is to mix and match—you can wear a Balenciaga bag with Topshop and H&M items and look absolutely amazing. Try and add original accessories to your outfit, whether it’s beautiful shoes or a bag. Every outfit can be spiced up by unique accessories. How she describes her style: A combination of trendy and classic. The one trend she’s keen on: Leather in all shape and colors and the come back of ’70s style.

Her best piece of style advice: If a guy says he hates it, buy it. How she describes her style: Clean lines with funky pieces thrown in. The one trend she’s keen on: Bucket hats and wide-leg jeans. Bucket hats because they’re hats (duh) and wide-leg jeans because they’re comfortable while looking like you tried (double duh).

Her best piece of style advice: You make your clothes. They don’t make you. How she describes her style: Elegant, regal, and simple. The one trend she’s keen on: Bottega Veneta square-toe mules.

Her best piece of style advice: Personal style is a journey, not a single stop destination. How she describes her style: Romantic and feminine with a modern twist. The one trend she’s keen on: Minimalist, wrap tie heeled sandals. Especially those by The Row!

Her best piece of style advice: I try to dress for my personal style and body type without succumbing to today’s fleeting trends. If I’m not comfortable with what I’m wearing I don’t feel like I’m presenting my most authentic self! How she describes her style: Fashion-forward, but definitely comfortable. I’m a casual dresser. Flats over heels any day and everyday. The one trend she’s keen on: Can’t wait to revisit suiting.

Her best piece of style advice: Keep it simple. Basic is not a bad thing. How she describes her style: California resort. The one trend she’s keen on: Seashells and straw woven accessories.

Her best piece of style advice: Dress for yourself. How she describes her style: Colorful, frilly, maximalist, and summer forever. Anything Carrie Bradshaw would wear. The one trend she’s keen on: Print mashup—wearing all the prints at once.

Her best piece of style advice: Wear whatever you want to wear. How she describes her style: Comfortably uncomfortable. The one trend she’s keen on: Sneakers with literally everything.

Her best piece of style advice: Always iron your clothes before going out. How she describes her style: Comfortable, tailored, classic and feminine with a boyish touch. The one trend she’s keen on: Puffed sleeves.

Her best piece of style advice: That style can be many things and not only one. One day you can be sporty, the next classic and so on….I’m inspired by too many things to stick to one style only. How she describes her style: Colorful, sporty and feminine always with a bit of vintage. The one trend she’s keen on: Long shorts

Her best piece of style advice: Confidence is your best accessory. You can put on anything and make it fashion as long as you’re confident in what you’re wearing and how you feel in it. How she describes her style: Versatile. Edgy. Chic. Street. The one trend she’s keen on: Straight leg, split hem denim.

Her best piece of style advice: Clothes are meant to be worn, not stored in a closet. How she describes her style: Classic looks, with NYC/Italian flair. The one trend she’s keen on: Shell anklets.

Her best piece of style advice: Buy pieces that are versatile. How she describes her style: Everyday is a different vibe. For the most part feminine, modern with a pop of color and occasionally edgy. The one trend she’s keen on: Square necklines with puff sleeves.

Her best piece of style advice: We can break the rules. How she describes her style: Creative, colorful and electric. The one trend she’s keen on: Square-toe shoes.

Her best piece of style advice: Classic investments never go out of style and a white T-shirt can take you anywhere. How she describes her style: Tailored chic with a pop of flair. The one trend she’s keen on: I am a ’70s girl, so I am excited to see a nod to ’70s style with high-waisted pants, and the continued return of floral dresses, and skirts.

Her best piece of style advice: You can rock anything if you feel confident in it. How she describes her style: High street chic. The one trend she’s keen on: Kitten heels.

Her best piece of style advice: Be yourself! Wear trends, but find a way to make them you. How she describes her style: Eclectic with some vintage mixed in. I’m not afraid to try anything! The one trend she’s keen on: Pistachio green.

Her best piece of style advice: Ex-British Vogue fashion director Lucinda Chambers once told me that of all the women she knows, the most stylish “is in her eighties and the other is in her sixties. I think [style] takes time, and that’s alright.” I couldn’t agree more—at 55, I’ve found my style groove, and it’s thanks to years of trial and error. How she describes her style: I like to mix things up. I have a sort of split-personality style: half minimal, menswear-inspired dressing, half bohemian, hippy-punk—with the occasional Advanced Style moment thrown in. The one trend she’s keen on: I don’t particularly follow trends, I’m more interested in style and what individuals are wearing. With the scorching temperatures, I’ve recently been wearing a lot of kaftan-style shirt dresses.

Her best piece of style advice: It’s not the item, it’s how you wear it. How she describes her style: Trendy and classic. The one trend she’s keen on: One shoulder tops.

Her best piece of style advice: To wear colors that are the most flattering for my skin undertones and clothing shapes that flatter my figure and height. How she describes her style: Sometimes romantic leaning and sometimes dressier. The one trend she’s keen on: Okay, it’s only August, but I love a beautiful faux fur jacket or coat.

Her best piece of style advice: My best fashion advice is to wear a smile on your face. How she describes her style: For everyday, I’m a trousers woman with a penchant for gold jewelry. I also like turtlenecks and a smart jacket. The one trend she’s keen on: Chunky gold jewelry.

Her best piece of style advice: Have basics of all colors for mix and match. How she describes her style: Basic and sustainable. The one trend she’s keen on: Khaki jumpsuits.

Her best piece of style advice: To lay out your outfit the night before—even if you end up wearing something completely different, you’re constantly putting thought into and checking in with your personal style. How she describes her style: I like to mix professional pieces with streetwear, I’m a sneakers girl, and I love a flare pant. The one trend she’s keen on: High neck crops and tanks.

Her best piece of style advice: It’s okay to spend a little more on quality basics. How she describes her style: California casual. I like comfy fabrics in neutral colors. I like to be a little soft but not too sweet. And I prefer tops and jeans most of the time. The one trend she’s keen on: Tie-dye! I never thought I’d love tie-dye as much as I did when I was in middle school, but I’m obsessed! My favorites are monochromatic colors

Her best piece of style advice: Never wear only black. How she describes her style: I would describe my style as a mix of classic elements with current items on-trend. I let what I’m reading at the moment influence how I see the world and that is often perceived through my style of the moment. The one trend she’s keen on: Heeled flip-flops

Next, see what women from all across the U.S. are wearing and shopping for right now.

Source: Who What Wear – Anna LaPlaca