How Not to Dress Old: The 2020s Edition

Oh, the drama.

I’m a nice person. Really and truly. And I go out of my way to avoid conflict and controversy. I don’t publicly discuss politics. Or Meghan Markle. And I’ve even been subdued in my backlash towards the mom jean.

I credit my discretion to Jesus and the patience that comes with being no-longer-25.

Still, and sadly, drama is not completely unavoidable. Take my most popular post to date, How Not to Dress Old. Between Pinterest, Facebook, and the blog, it has received thousands of comments. Thousands.

And 653,000 shares.

And there has been drama. People either love it or loathe it.

And while I know that telling people what to wear in this age-positive, body-positive era is tricky, at best, I also know that I’ve had 25+ years in an industry (fashion) that has not always been kind to women unless they are young, tall, and flawless. And I’ve had my own struggles with the idea of the concept of age-appropriateness.

I am almost-50 but feel 30 and probably, objectively, look 40. I am also curly-haired, petite, and exercise-averse. I once was described as skinny-fat. Which is basically two “insults” in one.

I have also, always, loved fashion. It is my favorite form of self-expression and truly my happy place. So I bristle at being told I “can’t” wear that and “shouldn’t” wear this.

In many ways, I feel like life begins at 50. I know that I am more confident, more courageous, and more fully myself than I have ever been. So why, now, when I’m just getting started, when things are starting to get better and easier and more comfortable in so many areas of life, do I need to feel restricted. It’s counter-intuitive.

I want to express myself more fully, not hide behind 50-year-old-woman clothes.

And so, for the naysayers and free spirits, for the rule-breakers and risk-takers, I hear you.

I, too, want to wear what I want.

But I also want to filter my style through the lens of age and experience and flattery and know-how that I’ve worked hard to acquire over the years.

I want it all.

I know that I have choices. And I choose the ones that help me express my beauty. That bring out my best.

Your choices may be different. Instead of simply feeling pretty, or sophisticated, or flattered, maybe you want your clothes to make you feel funky. Or artistic. Or edgy. There are no wrong answers. There is only personal style.

So this post, and the previous one, are supposed to serve as guidelines. Suggestions. Opinions.

Use what works for you and ignore the rest.

And now, the 2020 Edition of How Not to Dress Old, with updated pieces and current trends. As always, you’ll find everything I feature here in his catalog. And, as always, pictures are linked for easy shopping.

The Bolder Blazer

Ah, to be tall this season. Then I could wear all the long things and boxy things and oversized things and not feel like I am clothed in an expensive, menswear-printed tent.

It’s the opposite of the Emperor’s new clothes. So. Much. Fabric.

However, after seasons of the traditional fitted 1-3 button blazer, fashion was ready for a fresh new look, and this season’s squared-off silhouettes are definitely different.

I know that I’m always saying how a jacket should have the princess seam in the back to define your waist, but this season, many of the styles are intentionally boxy, with strong shoulders and a straight cut that ends somewhere below the bum or hips.

In addition to a blazer, you’ll find the new leather jackets as well as updated, elevated trenches with the same silhouette. Some styles, particularly trenches, feature belts for times when you want that waist definition. Also fun and fresh: cropped jackets, leather blazers, and long, drapey crepe blazers with waist ties, which can be super flattering.

How to Wear This Trend IRL (In Real Life): Consider proportions — both the jackets and yours. Petites, like me, will want less fabric and length. And unless you are very tall and slim, wear the new straighter jackets over something more fitted for balance.

In Your 20s

Do you even need guidelines? Fashion is your playground, and you can embrace all the trends if you love them. Understanding your body type, and how to flatter it, is important at every age, but beyond that, wear what you want.

In Your 30s

The 30s are the best time to get dressed, in my opinion. You can still wear almost all of the trends, but the added experience and sophistication make your outfits more polished.

In Your 40s

This decade calls for more sophistication and glamour, and less “I woke up like this.” An updated power suit is a great idea if your lifestyle calls for it, or choose a chic, structured blazer in plaid or a solid color.

In Your 50s

This decade, choose elevated, modern classics and the best quality you can afford. With your wardrobe color palette in mind, you can invest in staple pieces in gorgeous yet versatile accent colors as well as neutrals.

In Your 60s

It’s easy to fall back on the tried and true items in this stage of life, but it’s important to add a few updated pieces into your wardrobe from fashion-forward retailers that still work for your stage and style.

In Your 70s (and beyond)

You’ll want to focus on form and flattery, and on choosing colors and silhouettes that bring out your best beauty. Don’t be afraid of color. It’s a game-changer, a face-flatterer, and a mood lifter.

The Shorter Dress

The minidress, you guys. It’s everywhere, and it’s itty bitty. I mean, less is definitely less when it comes to the minidress, even for us shorties.

Every year, it seems that prom dresses are getting shorter and shorter, but I’m one kids-these-days comment away from sounding like someone’s great-great-aunt, so I’ll stop rambling and leave this picture right here.

Whatever happened to modest is the hottest? Anyway, these are not dresses for real life and real people, who move and eat and get out of cars and stuff. These are dresses for standing in clubs and holding your breath.

For the rest of us, there’s the shorter dress. Infinitely more flattering on the shorter woman. Here’s the height/length breakdown, as I see it.

Tall + slim = Any length dress you want

Tall + Curvy = Any length dress you want

Short + Slim = Knee length and shorter, as well as the occasional slinky or fluffy midi-length (i.e. a tulle skirt, satin skirt). Side-slits are a plus.

Short + Curvy = Knee-length and shorter, as well as an occasional slinky midi-length. Side-slits are a plus.

The question to ask, when choosing a dress/skirt length, is how do you feel about your legs. Love them? You can show a little more. Not so much. Then find your favorite spot on your legs and have your skirts end there.

Where the hem goes, there the eye will go also.

And here, some chic short dresses, by decade.

In Your 20s

If you love your legs, go short for sure, but remember that you want to be able to move freely and truly feel confident in your clothes, so pick a length you can live with.

In Your 30s

Go mini or slightly longer, as the decade progresses, but don’t be too quick to cover up your legs if you love them. You can still wear pretty much all the lengths at this age.

In Your 40s

Shorter is fine if the rest of the dress is modest, or go for a length that’s just a bit above the knee. Flattery and elegance become more important.

In Your 50s

Just above the knee is probably the shortest length you’ll feel comfortable in unless you’re quite petite and have great legs. Try the new tights if you want a shorter length but still feel the need for some coverage.

In Your 60s

Just above the knee to knee length is going to be the best choice for you. At most ages, showing off just one part of your figure (legs, back, neckline) at one time is the easiest way to keep from being over the top, and that’s especially true in your 60s.

In Your 70s

Knee-length is probably as short as you want to go, unless you have the legs or personality to pull off a shorter length. Choose streamlined silhouettes for maximum flattery.

I hope that you enjoyed this tour of the trends, by decade. And now, I’d love to hear your thoughts. Did you agree with my picks? Love them? Loathe them? Share your thoughts below.