What to wear in 2020 over 40

A high school classmate of mine recently pointed out that I should change my hashtags from #over40 to #over50. Even though my 50th is not for a couple of months.

He is dead to me.

Seriously, though, whether you’re #40andfabulous or #50andfashionable or #60andstylish or #30andthriving or… you get the idea. It isn’t about the number. It’s how you feel about the number.

We can be #50andfashionable or #50andfrumpy or #50andfatigued or #50andfedup. Clearly, I’m on a roll.

And the choice, largely, is ours. As is the choice of what to wear. It’s as individual as you are. In the virtual style scavenger hunt that is currently underway in my private FB group, I asked members to post pics of items that they felt were too “young.” Some seemed obvious, like skimpy minidresses and string bikinis and short shorts and plunging necklines.

Others were more surprising. Denim showed up a lot, particularly ripped or shredded or distressed. And, I know I’m getting controversial here, but not all ripped denim is bad. Unless, of course, you hate it. Or it’s not your style. Or it’s wayyyy out of your comfort zone. In my opinion, a little wear and tear is fine, but huge gaping holes are out of the question. For pretty much anyone. But that’s just me.

And so I want to preface this list of trends by telling you that it’s highly subjective. As you may know, I’m very opinionated. And this is where I share my opinions. It’s curated to reflect the things I believe real women will wear, with some more fashion-forward stuff sprinkled in.

I spared you the fancy bralettes. And the hot pants. And the crops tops and see-through plastic stuff. Oh, the horrors these eyes have seen.

But I’ve also saved you the frumpy fashions posing as trends. The A-line denim midi skirts. The menswear-inspired suits with enough fabric to double as tents. The voluminous dresses with sofa-inspired prints and high, scratchy necklines. Trendy or not, they are instantly aging and so, so hard to wear.

I kept the trends that are worth wearing, the easy updates and flattering silhouettes. And, of course, there is a catalog with all of these finds in one place, but I’ll share the list, and some highlights, here. Presenting my carefully curated, stylish-yet-subjective list of the top trends of 2020:

Tank Tops

A tank is the new tee, people.

Ditch those tired tees and stock up on some timely tanks. (I know I got a little carried away with the alliteration. Also, I didn’t mean a word of it. Of course you can keep wearing your timeless tees. Please. Fish them out of the trash. That’s better)

Seriously, though, tanks are totally trendy, and I’m not just talking about standard ribbed styles. There are square neck tanks and button-front tanks and high-neck tanks and fancy tanks. And if you don’t love your arms, they are perfect layered under blazers and cardigans, which are also trendy, BTW.

Turtlenecks

Another classic posing as a trend, this staple mostly made the list because it’s being worn differently (i.e. layered under a button-down shirt) and because of the profusion of options. You can find them in filmy sheer fabrics, t-shirt style knits, clingy cashmere or chunky wool. Patterned, printed, cabled or solid.

There’s a turtleneck for everyone. Unless you have a full bust, in which case a fitted turtleneck might not be your best bet. Unless you want your bust to look, um, fuller, and then go for it.

Short Dresses

Ahh, the short dress. How us short people have missed you. Some magazines have dubbed them minidresses, but you won’t hear that kind of language around here. Because, hate mail.

Now short is, like many fashion terms, subjective. There’s something for everyone out there, from microscopic to mid-knee, and they’re all calling themselves short.

For those of us, like me, who are actually short, this is a welcome change from a couple of seasons of hard-to-wear midis. And if it’s a little outside of your comfort zone, remember that short and flouncy is always going to be easier to wear than short and clingy. We should probably just skip those entirely, okay?

Bermuda Shorts

Did I ever tell you guys the story of the gorgeous purple Tory Burch Bermuda shorts I willingly gave away because they were, well, Bermuda shorts? It’s a nail-biter. Seriously, though, as stylish as these are this season, I cannot pull them off. They make me look short and scrawny. Never mind that I am short and scrawny. I don’t want to look it.

If, however, you are neither short or scrawny, then these are the answer to your short dreams. Dreams about shorts, I mean. If you were to actually have those, which would be weird. Anyway, they flatter curvy women and tall women and many women. And if, like me, they don’t seem to work for you, go for a slightly shorter style, between mid-thigh and knee, for a leggier look.

Frilly Stuff

Now I know this isn’t a single item, like the ones above, but in the interest of brevity, I’ve decided to lump tiers and ruffles and pleats and full, frilly sleeves into one feminine, flattering category.

If they strike your fancy, then you’ll find knife-pleated skirts and full sleeves to be quite becoming. (I’m trying to bring back that phrase. It’s my favorite). Artfully placed ruffles and tiers, which skim over the body and hide lumps and bumps, are also surprisingly easy to wear.

Polka Dots

Dots are just darling, don’t you think? I’ve always been a fan. For a true dot lover, like me, bigger is always better, and I love polka dots the most when they’re bold. Whether you like your dots subtle or spirited, they are everywhere and on everything this season.

Denim on Denim

It’s hard to call denim trendy when it’s never not in style, but there does seem to be so much more of it this season. And so much of it worn all at once.

I like to tackle the really big and controversial questions here. Pantyhose. Capris. And now, denim on denim. The diciest of them all. But, hey, someone’s gotta do it. The thing about the denim on denim trend is that you either love it or hate it. There really is no middle ground.

Except for me. I’m on the fence a little bit.

I’m all about a chambray shirt tucked into jeans, but a denim jacket worn with denim jeans just isn’t my style. Of course, that might change as my eyes gradually adjust to the combo, but it’s unlikely. I’m still warming up to the mom jean, and they’ve been trendy for years.

The upside is that denim is being used in every possible way this year, from shorts to dresses to skirts and tops and, of course, pants and jackets. And there’s a denim silhouette for everyone, from skinnies to wide-legs. The mom jean is still a thing, but flares and bootcut styles are also back in a major way. The trickiest trend? Wide-leg pleated jeans. Not for the faint of heart. Or the short of stature.

Menswear

Menswear is one of those trends I really, really love. On other people. On me, it feels a bit costume-y. It might be my extreme girliness. Or the fact that some menswear silhouettes seem to swallow me up. This season, however, I am loving elements of this trend, like the patterns (plaid! houndstooth!) and a slightly slouchy blazer worn with an otherwise feminine outfit.

Whether you’re all in on this trend or, like me, prefer it in small doses, you’ll find this season’s best vests and jackets and suits and loafers in the catalog.

Peplums

Peplums are popular again, but for those of us who never stopped wearing them, they’ve been a favorite for several seasons. I adore a peplum’s ability to define a waist and hide a tummy pooch. My favorite top, a merlot colored thick ponte knit peplum, is the most flattering thing I own. I love it so much that I decided to have it made in multiple colors by a seamstress.

If you haven’t discovered the power of a peplum, try one for yourself. When you find one you love, buy it in every color. You won’t regret it.

Monochromatic Outfits

This isn’t your mother’s monochrome.

When most of us think of monochromatic outfits, we think of head-to-toe neutrals, and while that is classic and always flattering, it isn’t the look that’s trending right now. This season’s monochromatic looks feature head-to-toe color. Whether butter-yellow or a bold blue, whatever hue you choose, a simple, flattering way to pull this look off is to wear that color head to toe.

Finally, a trend that makes me look taller.

Love them or loathe them, these are the trends you’ll see in stores this year. And since one of the easiest ways to #fightfrumpiness is to keep your wardrobe current, working a couple of these into your wardrobe will keep it fresh and contemporary.

Now I’d love to hear from you! Which of these trends will find its way into your wardrobe?