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Readers, here's a question to ponder for today: is anything truly classic in fashion? And if so, what is it?
I've written before about how when skinny jeans started to come back into style I clung to my bootcuts, insisting that they were a classic look (and one that flattered me). As I write this I'm still not sure I would disagree with the idea of bootcuts as classic, particularly since they're coming back in fashion now, but what I found was that the things you wear with denim — boots, tops, jackets — all changed to accommodate the look of a skinny jean silhouette, so eventually I felt outdated to wear bootcut jeans.
Mark my words, it will happen again as we swing back to denim with more volume on the bottom — it's the fashion industry's way of making everyone toe the line and completely replace your wardrobe every ten years.
(I've said before that I feel like denim trends do influence workwear in significant ways, so keep an eye over the next few years — I wouldn't be surprised if slim leg ankle pants, the roundest of ballet flats, and untucked/voluminous blouses all start to be scarce…)
Readers were recently discussing long necklaces and whether they were in –and I know this question has come up with regards to brooches — so let's discuss. What does “classic” mean in the fashion context? And what looks or items would you include in the list? Is it a specific base item you adhere to (e.g., bootcut jeans) or is it something more akin to style?
{related: how to cultivate style}
Things I might argue are classic (but I suspect readers will fight me on at least half of them):
- a crisp white blouse
- pointy-toed kitten heels
- pointy-toed flats
- stilettos
- pencil skirts
- a sleeveless sheath dress
- a red lip
- classic fitted trench coat
Some of our favorite work skirts of 2024 include classic pencil skirts like those from J.Crew,* Ann Taylor, Black Halo, Calvin Klein, Theory, and this Amazon seller) — but see the full post for all of the trendy styles also! (Also: readers love these slip shorts for comfort with bare legs!)
Some of the best dresses for work as of 2024 include options from J.Crew, BOSS, T. Tahari, and Lands' End. For really affordable options, check out Quince and Amazon sellers Miusol or MUXXN. We've also rounded up the best plus-size dresses for work!
There's also a list of items that are NEVER “fashionable” but would qualify, I'd argue, as classic, at least in certain parts of the country: pearls, twinsets, Ferragamo pumps, Chanel flats…
What say you, readers? Is anything truly classic in fashion? Are you making purchasing decisions based on it (i.e., investing a bit more in the workwear pieces you think are classic?)?
Photo of Audrey Hepburn courtesy of Photos for Class.
But see…
Lana Del Raygun
Interesting, I think of pointy toes (and very round toes) as trendy. Almond toes look more classic to me.
Anon
Agree.
Classy
Also agree.
Anonymous
Agree. I hate the pointy toe. Especially for those of us with larger feet.
Anonymous
Obviously not
NOLA
It’s interesting that the platform pump (which some would argue was more comfortable) has gone out of fashion to be replaced by what I consider a much more classic look. My only pair of Pradas is an absolute classic pointy toe stiletto pump, but in a light cloud blue. I feel like they look timeless and are less likely to go out of style. My other truly designer pumps are the opposite – Jason Wu t-straps in a high stiletto with a metal toe plate. But they are completely bada$$.
InDesign
The problem for me with platform pumps is that so many of them read as: hooker attire.
Anonymous
This. I don’t think I’ve seen many platform pumps that don’t make me think hooker. And yes, I’m looking at you, Jessica Simpson’s shoe line.
Anon
A single, particular item? No, I don’t really think so. Minor details like proportions and embellishments can look out of date. A type of item, like a black pump or white blouse? Yeah, absolutely.
Senior Attorney
This. Yes, a crisp white blouse is always in fashion, but any given crisp white blouse may or may not be. Giant collars and cuffs come in and out, buttons may be big or small or covered or not, the blouse may button all the way to the neck or only partway, and so on. The trench coat may have set-in sleeves, or dolman sleeves, or giant shoulder pads, it might be double-breasted or single-breasted, might be lighter or darker tan, and so on. Categories of items may be timeless but any given item is not.
AnonZ
Yes, this exactly.
Plus, the current definition of “timeless” seems to start around 1960, which is a long time for certain things to stay in fashion but a short time in the overall history of fashion. Everything will go out of style eventually – we’re not here discussing the pompadour as a timeless hairstyle for women even though it was fashionable for decades.
Idea
This. Like even with a sheath dress, Jackie Kennedy wore one kind of neckline, Michelle Obama another kind of neckline or waist, Melania Trump a different kind. You can tell the difference from a 1960s look to the Brady clothes to the 00s and now. Everything changes a little bit
Anonymous
I feel that if you are someone like Iris Apfel, you could wear something for 40 years straight and rock it every time. But most people are not Iris.
Senior Attorney
That brings me to another theory I have: Iris Apfel looks timeless because she doesn’t aspire to be classic. The getups she wears are never out of style because they were never in style to begin with. I once bought this amazing St. John knit suit at a consignment store: it was off white with a turquoise leopard print and it was divine. I wore it for years until it got ruined at the dry cleaner, and always got tons of compliments on it. It was probably 10-15 years old when I bought it but it never felt out of style because it had never been in style in the first place.
Vicky Austin
Hahaha, that is a great point. Something probably never looks dated if it *doesn’t* evoke a very specific decade.
Ariadne
Yes this. I think that something artsy or that has harmonious proportions and is unique can be worn without looking dated, because it was never really in, and therefore never out so to speak. My mom always wears very unique pieces that may have and element of a trend yet they rarely look dated. She is also a designer /artist and now retired, but all her friends, who are by far wealthier, and can afford amazing items, love to take her shopping because she has that ‘artistic eye’ thing going. They are amazed at the items she wears as they are not expensive, but her colour combinations and outfits receive so many compliments. She doesn’t do the Iris look, but it is her own artsy/ sporty/ fashionable look.
Irish Midori
I’m with you 100% on the pearls. They are timeless. I’m finding myself more and more willing to invest in white blouses, too.
Anonymous
Not all pearls are for all people and all situations. Nancy Pelosi’s pearls are awesome, but she wouldn’t be wearing some 7mm 18″ strand, either.
Anonymous
I agree. I love pearls. I wish Sarah Sanders would quit wearing them. I hate when they start looking like a uniform.
But, again, some settings or lengths look more up to date than others. A delicate solitary freshwater pearl from somewhere like LeVian will look a lot more current than opera length pearls with a suit right now.
Irish Midori
Threadjack question: I am toying with the idea of getting a new professional headshot. I’m not looking for a job, but I’m starting to branch into a more “consumer” focused practice that requires me to hustle for my own business, and I think building my own “brand” is going to be a good way forward. My company doesn’t really do this particularly well–it’s more of a “friend with a nice camera and oh here’s a blank wall you can stand in front of” operation. Where would I look to get something professional without breaking the bank (since this is almost certainly on my own dime)? What do I look for? Most of the internet searches turn up baby and wedding photography freelancers. Are the skill sets for professional head shots close enough that I can just go with one of these?
Irish Midori
Also, what should I expect to shell out for this?
Anon
If any of your friends are solo practitioners, consultants, etc., with nice head shots, ask them where they got them done.
I paid $200 for mine.
Sadie
Ask some Realtors :)
No, I wouldn’t go with a wedding/baby photog unless you have people who have used them for headshots recommend them.
Senior Attorney
You should be able to search for “business headshots” and come up with some options.
January
Well, I’ve started buying more slim-leg ankle pants, which is a definite sign that they’re nearing the end of their lifespan. ;)
Irish Midori
Haha! Exactly how I feel about fashion. Related: I’m so happy yoga pants are finally giving way to sweatpants. That’s a trend I can get behind.
Anon
This is so me!
Anon
Are you me? I feel like the second I finally get on board with a trend, it’s declared “out” (shrug)
Twinsets
I used to be on TeamTwinSet, but I haven’t see anyone wear one together in ages. I used to wear them together all the time (to the point where if I get the cardi, I must get the shell, and vice versa). Now just one at a time.
Lilly
Wearing one today. However, my look is old style prep mixed with modern minimalist. I’m an Old, and this has been my look since I was a teen. I’m even unironically wearing pearls. Today’s outfit’s concession to what is current is that my slingback pumps are the AGL pointy toe block heel ones in a deep red. I guess my point is that twinsets work for my look, so I wear them, and I think if a twinset or anything else works for your look and is appropriate to your dress code for the day, go for it.
InDesign
I love seeing women who can pull off a twinset. I can’t. I find it such a classic, American sportswear kind of look. And I agree–dress for your look & dress code.
Drago Cucina
Until a couple of years ago I wore them all.the.time. It’s running joke that cardigans are the lab coat of librarians. The slim skirt and twin-set evokes a timeless look to me.
Anon
What is everyone’s thoughts on classic suit styles? I don’t wear suits to work and anytime I have an interview, I freak out and pull out my old Express suit (ugh) circa college graduation 5 years ago. It is just a plain black suit with a flare leg and it is not tailored to me. I want to invest in a quality black suit for future interviews and have it tailored, but I’m not sure about styles, particularly the pant cut. Slim leg seems to be in style right now but I’m petite so I’m not sure if a slight flair looks better (makes my legs look longer?). I’m very suit ignorant so any other advice is welcomed.
CR
Practically every suit I’ve ever owned for 20 years has come from J.Crew or J.Crew Factory. If you want a suit that stands the test of time, a suit with a pencil skirt is your best bet. Aim for a jacket that isn’t overly long or short, I.e., isn’t overly trendy.
M
I am completely in love with suits by Hugo Boss. I prefer the dress with jacket look – but the pants are a classic option as well. I now own three – but the classic black is still my preferred interview look.
journo
Alternatively, since you don’t work in a field where you wear suits, you can pair a black suit jacket with a neutral pencil skirt or suit jacket over a dress. My industry is business casual generally or a structured dress, and I think the suit combo look is professional and more dressy than when I’m dressed well for a normal work day in a structured dress with a cardigan.
I have Banana Republic suit jackets and different brands of skirts, Loft, The Limited, BR, etc.
Anonymous
A more formal interview suit is always a skirt with a proper white shirt (like a mans dress shirt with buttons/French cuffs and buttons all the way down). Some places it would be okay to wear a blouse or a shell with the suit or a suit with pants or a dress.
Most formal is a skirt suit.
C
I think it’s easier for accessories to be truly classic than for clothes. Pearls, obviously, but also things like diamond studs, solitaire rings, and simple pendants are unlikely to ever go out of style.
anon
I will be so very happy when the ankle pants and loosey-goosey work tops go away. Both are really unflattering on me. For whatever reason, I look so much better in more tops with structure or run narrower through the shoulder, which is the opposite of most women I know.
Gemma
Aha! This explains why I have trouble figuring out when to wear my classic Ferragamo heels (with the leather bow). They make every outfit look so uncool.
Anonymous
I don’t try to be on trend, because I think it’s a fashion industry scam. I know certain cuts and colors look good on me and when the industry elects to make them available I stock up. The rest of the time I shop my closet.
Anonymous
I love my Ferragamo Vara low pumps!! Wore them through pregnancy and hauling DD to daycare. I don’t care if they aren’t fashionable, they are tasteful and work appropriate. Anybody with taste recognizes them as a classic from their time, which is the key. Like the Hermes Birkin or the Cartier watch or Todd’s loafers or Burberry trench or Levis 501s or any white tshirt or cashmere crew sweater.
M
Same. I am obsessed with Varas (which I greatly prefer to Varinas). My favorite is my red patent pair. They add a pop of color – but are still timeless, classy, and sophisticated (and comfortable!).
Anonymous
The only thing on that list that I would consider “classic” would be the crisp white blouse (or shirt). I would not be caught dead in any of those other “classics” except perhaps for the trench coat. Pointy-toed shoes are out–even I didn’t dislike the look–because I’ve got bunions and don’t like the sensation of red-hot nails pounded into my feet. Stilettos are bad for the back and hips as well as the feet, and heels make a woman walk in an ungainly, unnatural way. And I loathe sleeveless dresses (and those cretinous designers who declare that sleeves are “frumpy”).