Old Outfits Updated for 2020

When you’ve been sharing outfits on the internet as long as I have, you’re bound to have some misses. I cringe when I look back at pictures from 5 and 10 years ago, and even some of my outfits from 3 and 4 years ago have a way of looking dated.

I’m sure we all have those moments as we look through old family photo albums, but my pictures are documented on the World Wide Web for all to see!

Oh, well. It’s too late to go back now.

I have to remind myself to give 2012 Jo-Lynne some grace. I’ve learned a lot about fit and proportion and how to dress my body in the past 8-10 years. Plus, of course, styles change.

For example, we were all wearing our skinny jeans long and bunchy at the ankle in 2012, but that looks so sloppy to me now.

Of course, I’m sure the same will be true in 2030 when I look back at pictures from 2020. That’s just the way it goes.

As an aside, I cannot get over how short my hair was in 2012. I never liked it short, but it was thinning badly, so I had to cut it. I’ve spent the last eight years trying to get it healthy and growing it out.

Any-who! Today, I’m taking a few older looks from the blog and showing how I would tweak them to look more current for 2020.

Before we begin, I just have to say one thing. When I write posts like this, picking apart outfits and making suggestions for modern tweaks, there are always a few people who get defensive or take my comments as a personal affront to their own clothing and styling choices.

Listen, folks. There is really no right or wrong here, and of course we should all wear what we like and feel good in. The fashion police aren’t going to hunt you down and give you a ticket if you don’t front-tuck your shirt.

This is just how I would personally update these looks so that I feel modern and current. I hope it’s helpful.

Old Looks Updated for 2020

Let’s start with this picture that I shared in my Facebook Group the other day.

Utility Jacket with Stripe Tee, Black Jeans & Booties, circa 2017

I came across this post from fall of 2017 when I searched utility jacket on my blog, and I got a laugh out of it. At first glance, this outfit isn’t horrible. I mean, it was only three years ago. But it could use a few tweaks to bring it into 2020.

The first thing I noticed is the fit of the jacket is a little off. It’s too big in the shoulders and arms, and it looks a little rumply (maybe it just needed an iron) but it’s a classic wardrobe piece that I would still wear today.

Another thing I noticed is the length of the shirt — it’s pretty long and has a way of cutting me in half vertically. Today I would wear the same shirt and front tuck it, or it could be hemmed to a more flattering length.

But what really made me laugh is when I saw this picture, with my jeans falling into my booties. #justno

I guess we all did that? Or maybe I was just oblivious to it at the time.

So anyway, here’s would I do to make this look more current for 2020…

Utility Jacket with Stripe Tee, Black Jeans & Booties, circa 2020

The first thing I would do is shorten the jeans — either by hemming or cuffing (or just cutting them off and leaving a raw hem) and then I’d front-tuck the shirt. I could have done both of those things to the outfit above, and not purchased a single new thing.

But since I’m recreating this outfit three years later and no longer have those pieces, I wore this rounded v-neck tee in stead of the original boatneck tee, and I gave it a front tuck to keep my proportions in balance.

These black skinny jeans have a 27″ inseam, rather than the 29″ inseam of the ones I was wearing before, and I have a pair of very similar booties.

Finally, I wore the Caslon utility jacket I picked up at the #NSale this year. There’s nothing wrong with a classic utility jacket (as in the 2017 outfit) if you like the style, but personally, I’ve never loved the look on me so I finally got rid of all mine.

This one is a little bit shorter and more structured, and it just fits me better overall.

Also notice how much better it looks with the sleeves rolled. That little trick always makes an outfit look a little more styled, and it can help disguise sleeves that are too big or too long. (You can also push them up, rather than cuffing, for an even more modern look. I’m just too lazy to figure out how to make that work.)

I feel like this 2020 version of this outfit fits me better overall, and the shorter jeans and front-tucked top create a better balance and a cleaner appearance. The only thing I might want to add here is a belt, but it doesn’t really need it.

Chunky Turtleneck with Skinny Jeans and Leopard Flats, circa 2015

This outfit looks really frumpy-dump to me. I’m not sure why I thought it was cute enough to photograph.

A few things jump out at me about this outfit right off the bat. The sweater is simply not flattering. The chunky cable knit adds visual bulk, and the big ribbed fold-over turtleneck looks like I’m wearing a neck brace, but neither of those factors is what really dates the outfit.

It just isn’t the most flattering on me due to my body type. (It’s also a size too big, which I mentioned in the original post.)

What does date the look is the length and wash of the jeans. Sometimes I come across older photos on Pinterest of popular fashion bloggers I follow, and the length of their skinny jeans is always a dead giveaway that it’s an older post.

At the time, it looked right, but now I think the longer length looks so sloppy. It’s amazing to me that we all wore them like that. I know the cropped trend won’t stick around forever, but hopefully the pendulum won’t swing back this far! Ankle-length jeans are my favorite.

The other issue with the jeans is the wash and the two slit knees. They’re a quality premium denim brand (DL1961) and I’m sure they were in style at the time, but denim washes and distressing techniques have come a long way in 5 years.

I also find it funny that they were considered skinny jeans, as they look pretty straight to me. My daughter walked in while I was working on this post and asked me why my jeans looked so long and baggy. Even the 15 year old can tell this isn’t flattering, lol!

Now, in my defense, when I look back at most pictures from 2015, my jeans did fit better than this. I think these were just an unfortunate choice, but I guess I didn’t see that at the time because I wore them quite a bit.

And the shoes… while leopard ballet flats are a classic, loafers and pointy toe flats are more on-trend at the moment. Or a boot would have helped to offset the bulkiness of the sweater and create a more pleasing balance.

Chunky Turtleneck with Skinny Jeans and Flats, circa 2020

While I love a chunky turtleneck sweater, they just aren’t always the most flattering on me because I have wider shoulders and a larger chest. Plus, I think I must have a shorter than average neck… that’s a thing, right?

And yet, I do live in Philadelphia and tend to be cold-natured, so I like to wear cozy sweaters. I just have to choose them carefully.

In the 2015 outfit, I could have given that sweater a front tuck, but that’s hard to pull off with that style of sweater. It would have been better to pass on it and find one that is an inch or two shorter, and of course to buy the right size.

FIGHT THE FRUMP TIP: Wearing clothes that are too big will make you look frumpy. Fit is so important. And so is wearing what works best for your unique body.

I’ve learned that a cowl neck or relaxed mock neck are more flattering for me, and I try to stay away from super chunky knits. Again, these aren’t things that make the look dated, but as we age, we hopefully learn to choose our wardrobe items more wisely.

In this case, I picked a different style of sweater altogether. This one has a shorter mock neck, and while it has some ribbing in the knit for texture, it’s not as thick and bulky as the cable knit sweater above. I also prefer the straight hem to the big contrasting ribbed hem.

From this side view, you can see how much more streamlined and slimming this sweater is than the one above. It still reads as a cozy, chunky knit, but it’s not as bulky and cumbersome.

I also wore skinny jeans that are a couple inches shorter (these have a 28″ inseam, as opposed to the 30″ in the ones above) and the raw hem is more modern… although I have no problem with classic denim hems either. I wear both.

These jeans also fit me better than the ones above. They have more of a legging fit, so they’re slimmer through the calves; and because they’re shorter, they don’t create bulk around the knees or ankles. This gives me a long, lean leg line from hip to hem.

Finally, I swapped the leopard ballet flats for leopard pointy toe flats. I love the ballet flats from the picture above, but I feel like these look a more polished and sophisticated, and a little more NOW.

I could take this outfit a step further, and wear ankle boots rather than the pointy toe flats.

Either are in style, but the booties look a little more modern and create a bit more balance. Since they’re bulkier than the flats, they help offset the chunky sweater on top.

Styling Note: In this case, my jeans have a 27″ inseam, and the booties have a lower shaft, so they just barely meet at the top of the shaft. This gives a much cleaner look than if the jeans were bunching on top of the bootie or falling inside.

And here’s another version, where I cuffed the jeans with a 28″ inseam to accommodate the booties.

In this case, the sweater isn’t really a chunky knit, but it’s soft and cozy with extra long cuffed sleeves and a shorter length — definitely a more modern, almost trendy look, than the two above. Also, the relaxed cowl neck is far more flattering than the big neck brace in the 2015 outfit.

Okay, I’ve got one more for you. These posts take forever to write! Brevity is not my strong suit, and it’s hard for me to analyze these outfits without using all the words.

Cardigan with Infinity Scarf and Skinny Jeans, circa 2015

I remember being so proud of this outfit when I posted it back in 2015. I was just starting to do fashion blogging full-time, and Paul was hard at work as my photographer.

And again, it’s not terrible, but that long t-shirt hanging down under the cardigan and the infinity scarf really date the look… and again, the jeans.

I will say this, though. I feel like these jeans are flattering — far more flattering overall than the ones in the two older outfits above — just not a modern look due to the length. But if they were shortened a bit, they would be perfectly fine for today.

In fact, they still sell them. No, this is not the exact same wash, but the dimensions are the same — 30″ inseam; 11 1/2″ leg opening; 9″ front rise.

The infinity scarf, however, severely dates the outfit, and this is why.

Infinity scarves were a new thing long about 2011. They came into style quickly, got really popular for a few years, and then disappeared. That’s a passing trend.

Traditional oblong scarves and square silk scarves are classic wardrobe pieces that rise and fall in popularity through the years, and you can style them in many different ways. They will never be out of style, per se, but they may be more “of the moment” some years than others.

Please don’t throw rotten tomatoes at me, but I recommend ditching your infinity scarves… and while you’re at it, those big square “blanket scarves” as well.

Now, for my standard disclaimer: If you lurve your infinity scarves and want to keep wearing them, by all means do so. It is entirely up to you. There are no rules here. But if you are interested in staying current, I’m telling you that infinity scarves are starting to look tired and dated. But if you love yours, by all means, keep wearing them. I just wouldn’t advise investing in new ones.

It’s much more modern to wear a more traditional oblong scarf, and if you want to go a little more trendy with it, the bigger, thicker, longer ones are really hot right now.

Cardigan with Infinity Scarf and Skinny Jeans, circa 2020

This outfit is from December 2019, so it’s not QUITE 2020, but who’s counting?

Now, let me say, I get that this scarf is not exactly flattering, but it’s the modern day “blanket scarf” — far more modern than the infinity scarf or the big square blanket scarf worn kerchief style that was also a passing trend.

Also note, the fit of the jeans (and the shorter length) and the ankle boots rather than moccasins.

And of course, I’m wearing a leather moto rather than a cardigan. I actually still like the marled cardigan in the 2015 outfit, but I don’t have a lot of cardigan + scarf outfits in my recent archives.

This is the only one I could find, and I don’t really like it. I feel like this outfit ages me. Cardigans are hard, you guys. Seriously, I am less and less enamored with them as the years go by.

Here’s an outfit with a scarf that I love. I’ve worn this many times in various ways over the past two years…

The sneakers keep it modern, but ankle boots work just as well. I will say, though, I am dying to chop off an inch of those jeans. They’re a 28″ inseam, and I really prefer the 27″ inseam with sneakers.

I also really love how a leopard scarf levels up a neutral outfit. This top-down selfie is from 2018, but I wear this exact same outfit (I still have this exact scarf —  it’s from J.Crew but no longer avail) a few times a year.

And that’s all I’ve got!

Want even more? I did a similar post last fall — scroll down past all the Try-Ons.

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