Fall/Winter Fashion
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Old Outfits Updated + A Few Random Try-Ons

Today’s post is a bit of a mish-mosh. I have a few try-ons, but not enough to warrant a whole post, so I’m also going to share a few outfits from that old fall outfit roundup that I recreated and updated with pieces currently in my closet.

Let’s start with the try-ons.

Fall Try On Haul: Nordstrom, J.Crew, Anthro & Everlane

By way of reminder, or for anyone who is new, I’m 5’5″ and about 140# with a short-waisted hourglass shape. I usually wear a small in tops, 6 or 8 (28 or 29) in pants and jeans, and an 8 in dresses. I’m also usually a size 8 shoe.

All links and descriptions are below the pictures.

Halogen V-Neck Top (size small) // I shared this top earlier in the season in the rust floral, but I didn’t keep that one because I didn’t think I’d get enough wear out of that color. This black-pink dot, however, I LOVE.

I first styled it with black jeans and pumps, which is how I’d most likely wear it. I like these faded black jeans with the shredded hem (similar) for going out to dinner but I’d wear my straight black jeans with the sewn hem (similar) for church or other conservative venues.

But this top is also perfect for work wear, and I get a lot of requests for that, so I also styled it with ankle skinny pants to show you how that looks.

VERDICT: Keeping

1901 4-Way Stretch Ankle Skinny Pants (size 8) // These are a great basic ankle pant to have in your closet. I love the fit (and I have a hard time with this style of pant, I think because most are longer.) These have a 26 1/2″ inseam, which is perfect on me. See how they end right above the ankle bone?

They also come in navy, and they’re TTS, or size up if in between. I often wear a size 6 in pants at LOFT, and I needed an 8 in these.

VERDICT: Keeping, in fact, I already had them.

J.Crew Gemstone sweater in supersoft yarn (size medium) // I mentioned yesterday that I found a cozy, festive sweater that I liked… this is it.

This sweater truly lives up to its name — I love all of the J.Crew supersoft yarn sweaters, although I will warn you, if you’re sensitive to wool, this sweater is made of polyamide, merino wool, alpaca, and elastane.

It’s cozy and practical with a hint of sparkle, and I love the traditional shoulder seems and extra long sleeves. It also comes in a pretty warm camel color, if that suits your coloring, and I LOVE the earrings they pair with it. They really help elevate it to a dressier look.

Fit-wise, it runs small, as I’m wearing a medium, and it just fits. Also, it’s only 21″ long, so if you prefer longer sweaters, you may not care for the length on this.

VERDICT: Returning. While I do like this sweater a lot, I’m not a big fan of the crewneck, and it seems pricey for what it is (although I did get it on sale.) I’m going to hold out for something similar that I absolutely love.

also wearing: similar black jeans with TB Minnie flats in black cherry

J.Crew Pointelle cable sweater (size small) // Now this sweater, I love. I will even forgive them for giving it drop shoulders. It is super soft, but it’s also light and airy, due to the pointelle knit. You don’t need an under layer, in that it isn’t see-through, but you might want one for warmth.

The pointelle cable knit is such a pretty pattern, and I like the straight cut and split sides. I also like how the mock neck, while relaxed, doesn’t fold down in front, if that makes sense. I have another one that never looks quite right, but this one seems to stay in place.

The 22″ length is perfect for me, and it runs TTS. (I’m wearing the small, and it fits as it should — relaxed but not oversized.) It comes in 5 gorgeous colors, and it’s currently 30% off with code SOGOOD.

VERDICT: Keeping! Love it, and I don’t have anything else in this color . . . well, that’s not entirely true.

When I went to put it in my closet, I also noticed this pink Vince Camuto mock neck sweater that I purchased a few weeks ago.

Vince Camuto Mock Neck Sweater (size small) // Since I had yet to take the tags off, I decided to try it on and compare. These sweaters aren’t so similar, that I couldn’t justify keeping both, but I would wear them the same way with pretty much the same pant and shoe combos, so I wanted to compare.

This sweater is also amazingly soft, but it’s a tighter weave, so it’s warmer. It also has a taller mock neck that is a bit stiffer due to its thickness and definitely holds its shape. It also has a nice texture to the knit, but not quite as feminine as the pointelle cable knit.

It’s 21 1/2″ long, so pretty much the same, but I did notice in comparing that it is a boxier fit — in fact, it almost balloons out in the midsection, where I most certainly do not need any added volume.

I did a side-by-side straight-on shot to compare.

They both have drop shoulders, which adds some bulk as well, but I prefer the cut of the J.Crew sweater through the body, and the lower mock neck is also more slenderizing somehow, although I like the high mock neck of the Vince Camuto for coziness and warmth.

VERDICT: I’m not sure if I’ll keep the Vince Camuto or not. For now, I’m keeping the tags on. It is a gorgeous shade of pink, and it’s very cozy and warm, but at that price point, I should love everything about it.

P.S. If you like it, it does come in other colors, and it runs TTS; the small fits me perfectly.

also wearing: Madewell 9″ skinnies (in 29 petite) and Vince Ridley booties

Okay, moving on . . .

Anthropologie Maggie Bell-Sleeved Sweater (size small) // Okay, sorry, I took waaaay too many pictures of this sweater, but I just think it’s so fun!!!

This sweater definitely has some boho vibes with the wide bell sleeves and subtle tie-dye print. I’m wearing the pink, but it comes in 4 other colors, and it’s on sale. (I try to only shop at Anthro when they’re having a sale because their price point is on the higher end.)

Oh, and they’re not all tie-dye. There is a solid ivory and a pretty grey ombre, as well as black and camel speckled knit. I find this sweater very soft and comfortable, but it does have 5% wool content, if that matters to you.

Also, if it looks like they only have XS in stock, they don’t. Just click on the other sizes, and you will see that you can add them to cart.

VERDICT: Keeping! Wore it last night to dinner, in fact, with grey jeans and booties.

Okay, one more for the try-on section . . .

J.Crew Funnelneck sherpa jacket (size small) // I got this in with my J.Crew Factory order I shared in last week’s try-ons, and I forgot to try it on! These sherpa jackets are super on trend right now, and it’s a nice fun, casual layering piece to have in your fall wardrobe.

It runs true to size, or size down if in between. I sometimes need a medium in jackets, but as you can see, this one in the small zips up, no problem.

VERDICT: Undecided, only because I don’t love this color. I’d rather have grey.

also wearing: stripe artist tee with  Madewell 9″ skinnies (in 29 petite) and Sorel wedge booties

Old Outfits Updated for 2019

So I posted a new fall outfit roundup earlier this week, and within that post, I made a comment about some of my older outfits looking dated. Well, that spawned a ton of comments wondering what I meant and which outfits I was referring to.

Which brings us to today’s post . . . I thought I’d go back through that old fall outfit roundup and pull out some looks that I can recreate/update for fall/winter 2019-2020.

I didn’t buy anything new for this, so I was somewhat limited by what I have in my closet, but in a way, that makes the challenge even more realistic. It also means I took some liberties and didn’t always recreate the exact outfit, but in I tried to use the same color palette in those cases.

So let’s get started!

#1 // black moto jacket +grey tee + black jeans + leopard flats

This first look was originally posted on November 2, 2015 — so exactly 4 years ago to the day! Granted, it’s very simple, but a monochromatic grey and black look with a pop of leopard was a novelty to me at the time. In fact, if you click over to that post, you will see how this outfit was inspired by another blogger.

black and grey with leopard

Updated For 2019:

The main thing I updated was the jeans — inseams have gotten a little shorter since 2015 (you’ll notice Jeanette’s jeans were longer as well) — and the raw hem gives these a more modern vibe.

I also wore a grey tee that isn’t as voluminous, but that older tee is really fine — I even had it front-tucked! But these days, we’re tucking our tops in a little higher to show the waistband of the pants, which also helps compensate for the shorter pants.

Granted, I’m only talking about an inch here. There is honestly nothing wrong with that older outfit, but I do like my newer version better.

My pointed toe ballet flats also help keep the look modern, and I prefer this genuine leather jacket to the coated denim one above.

The other thing I changed is the necklace — I’m still doing a layered look, but I’ve gone with a shorter pair of pendants, which looks a bit more modern to me.

similar black moto jacket //grey tee // similar black jeans // leopard flats // layered necklace

#2 // grey cardigan + pink tee + white jeans + grey booties

This picture is only two years old, and there is really nothing wrong with it, although I’ve since passed on the big, slouchy mom bag. Styles today are more structured and often smaller.

The other piece that I’m feeling kind of done with is the necklace. I still own it, but I don’t find myself reaching for it anymore.

Updated For 2019:

This is another outfit for which I had pretty much the exact same components — just updated versions. And I did think to grab a bag for this recreated look.

I really like this leather hobo from Treasure & Bond, and it’s a good price point for leather.

The white jeans are actually the exact same pair in both pictures, and while the rise is on the lower side for today’s styles, they will look fine to me.

You will see that I went with the shorter layered necklace again in this look, and my booties are different, although both still look current.

I also prefer this slightly more muted color palette, and the sweater I’m wearing here is better quality and I like the fit better, but the style of the one above is still on trend as well.

grey cardigan // pink tee // white jeans // grey booties // taupe hobo // layered necklace

#3. stripe tee + olive cargo pants + denim jacket + leopard flats

Here’s another blast from the past. This outfit was originally posted in fall of 2015. This is when pairing stripes and leopard print was fresh and new. (At least that’s when it was new to me.)

Again, aside from the lower rise and longer inseam on the pants, it’s still a relevant outfit. This old denim jacket was also cropped, and I prefer my current Vince Camuto denim jacket, but the washes are very similar.

stripes and olive with leopard

Updated For 2019:

As I pointed out above, my current denim jacket is longer, more of a traditional fit. And the only olive cargo pants I have in my closet at the moment are these cargo joggers, which are a little more casual than the skinny cargo pants above.

I wouldn’t put ballet flats with these cargo joggers (although I like them fine with the skinny cargo pants in the 2015 outfit) so I took a picture with my snake print sneakers, which are a similar color palette to the leopard flats.

Funny, I’ve worn this exact outfit with a white tee, a grey tee, and a graphic tee, but it never occurred to me to put a stripe tee with it. I do like it!

The lack of necklace in this case was not intentional. I would usually wear a pendant or the layered necklace from the 2 outfits above.

Also, rather than a burgundy crossbody, I’d carry a taupe or cognac tote or satchel.

similar stripe tee // olive cargo pants // denim jacket // leopard flats (or snake print sneakers)

#4. camel sweater + white jeans + plaid scarf + cognac OTK boots

This is another outfit I was super proud of when I originally posted it in 2016. I mean, first of all, you have the white jeans after Labor Day, but I also loved that teal crossbody with this scarf and camel sweater.

Updated For 2019:

I don’t have a plaid scarf at the moment, and infinity scarves have seen better days, so I recreated this outfit with a more traditional oblong fringed leopard scarf.

OTK boots are still on trend, but most are more of a slimmer fit than the ones I was wearing above. That said, I’m gravitating more to knee-high boots these days, so that’s what I wore with this look.

I’d probably carry a darker brown or lighter taupe/beige bag, but I didn’t think to grab one for this picture.

camel sweater // white jeans // plaid leopard scarf (option) // cognac OTK boots

#5. grey tee + denim jacket + burgundy jeans + black mules

Updated For 2019:

Now this one’s a stretch, I realize, but I don’t have burgundy jeans right now.

I’ve had a lot of questions about colored jeans still being in style, and honestly, I’m not really feeling them this season.

To keep your look current, I’d stick with darker, more muted tones — like a deep olive, or yes, burgundy or plum, as long as they’re really dark. But I much prefer my grey jeans at the moment.

I still have these mules, though, and a denim jacket and grey tee is classic, so I asked myself, What pants would I put with those three pieces right now?

This is what I came up with . . .

Yep, black.

I know… seems boring and not at all the same outfit. But I love these off-black jeans with the shredded hems with a grey tee and denim jacket (although I wish they were an inch shorter.)

I also prefer the lighter grey tee and mid-wash denim jacket to the darker shades above, and of course I front-tucked my tee this time. The untucked look above looks so sloppy to me now.

I just wish I’d thought to add my black O-ring belt.

grey tee // denim jacket // burgundy similar black jeans // similar black mules // optional: black belt (similar for less)

#6 // black moto jacket + grey tee + grey leopard scarf + burgundy jeans + grey rain boots

Again, I don’t currently have burgundy or plum skinny jeans, so I had to be creative with this one. Rather than wearing a different color jean with the other components, I decided to take this color combo and rework it.

Fall Outfit: LEOPARD + RAIN BOOTS

Updated For 2019:

The grey leopard scarf remains, but I brought the burgundy up to the top in the form of a puffer vest and wore black jeans.

I wore a grey sweater instead of a grey tee because that’s what I have, and I like the luxe look better, and I still have the grey rain boots (although they live in my daughter’s closet now.)

These rain boots are a little clunky, so I also tried this look with these Sorel wedge booties — a little more modern but just as practical.

I like this look best. In fact, I think this outfit is my favorite of all six that I recreated!

black moto jacket burgundy vest + grey tee grey sweater + grey leopard scarf + burgundy black jeans + grey rain boots wedge booties

So I don’t know if that’s helpful or not. I think most of the items in the older outfits are all still okay, it’s more about how they’re styled and put together.

As far as colored jeans and infinity scarves go, if you’re debating whether to keep or toss, I’d probably only keep only the ones I absolutely love.

I also find it interesting that the bigger, slouchy bags in those pictures look dated. I hadn’t really thought about handbag styles changing, but they have.

Again, I’m not saying to toss every one of your big, slouchy bags. If you love them and still use them, no big deal. But if you’re unsure, or just not feeling it anymore, maybe put it away for the season and see how you feel next year, or if you’re really over it, update to something fresh and new.

Don’t miss my neutral everyday handbag roundup with spend, splurge, and save options.

#7. yellow cardigan + leopard scarf + white tee + bootcut jeans + brown ankle boots

I shard this in my outfit roundup, but I thought it also fit in well here.

Undoubtedly my most pinned outfit of all time, this mustard cardigan with the leopard scarf and bootcut jeans is still relevant — it just needs a few tweaks.

Updated for 2019:

I didn’t have a mustard sweater in my closet, so I put together this flat lay to show how I’d update this look for current styles.

Bootcut jeans will look more current with a higher rise, and as I said above, I’m not feeling the infinity scarves anymore, so I replaced the leopard scarf with a more traditional style.

I also found a really cute mustard yellow cardigan from Topshop that looks a little more modern, although the grampa-style cardigan I’m wearing above is still okay.

leopard scarf // yellow cardigan // white tee // brown ankle boots // bootcut jeans // brown belt

And that’s a wrap! I hope it’s helpful.

As usual, the devil’s in the details . . . well, I’m mixing metaphors but you get the gist. These are all minor tweaks, but they can really make a difference.

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43 thoughts on “Old Outfits Updated + A Few Random Try-Ons

  1. Love this Jo-Lynne! So many of us pin your outfit pictures to remember combinations and this is so helpful, especially to see what you’re focusing on to update a look. I really appreciate how you’ve been explaining outfit details lately and showing the side by sides like the pink sweater pics makes it so much easier to see what you’re describing. And girl, whatever you’re doing to look the same age in pictures year after year is WORKING 😉

  2. Thank you! I love this post! You really did a great job tweaking each update. I especially love that you shopped your closet!

  3. Will you please make a road trip to NH and come organize me! I can look at my full closet and only come up with the same 5 outfits!!! 🙃

  4. Jo-Lynne
    You are so good at what you do.   You seem to put a lot of thought in your work and it is shows.  I’m older than your average audience but I do enjoy your posts and find I can still use a lot of your ideas.  Since I’m retired now, I’m putting more energy into how I dress and I’ve learned a lot from you.    Love your Facebook group as well.   BTW, love the lavender J. Crew sweater on you.  It drapes so nicely and looks so feminine.   Just want you to know you are very much appreciated!

  5. This was one of the best posts you have done. I love seeing the differences of older outfits and new ones. I like your attention to detail. I am not into the raw hem, but I like to see what is fresh verses outdated. After all, I don`t want to look like I`m stuck in a time warp!!

  6. I love this post! The way you re-created the looks for today is very inspirational. I also loved the side-by-side photos of the pink sweater. It really shows the difference.

  7. I love this! Definitely make this a regular post. Also, we seem to be wearing booties a little differently so you could update those outfits. Have a great weekend!

  8. Outstanding post. Love the side by side photos. You do not age!!!!!!!!!
    Agree that slouch big bags look tired at this point. I just don’t reach for them anymore. Edited all the infinity scarves last spring. They sorta swallow you up!!!!

    Great post. Thank you!!!!!

  9. This is definitely one of the most informative posts. Many of us have older pieces in our closets which start to look dated and we’re not certain if we should keep wearing them. I appreciate the remarks you’ve made that help determine why a garment no longer looks good. 

  10. Absolutely loved this post, Jolynne! Please do more like it in the future! With small tweaks, these are still great outfits. Especially like how you articulated the small changes to make them updated. I rarely comment, but look forward to your posts every single day. Thank you for all that you do to keep us in the know and fashionable!

  11. This is such a helpful post!  I’m glad you are keeping the J Crew sweater.  In the side by side comparison I can see that it is more flattering on you than the other one. 

    The new trend of higher waists, shorter inseams, and short tops or front tucks is not flattering for my particular body type. I’m tall and very short waisted, so I look much better in low rise and long tops.  How do you adjust for new trends when they aren’t very flattering on your body?  You seem to have pulled it off.  Is it the addition of a longer third piece such as a vest or cardigan?

    1. I hear ya. I struggle with that too. And of course we should wear what looks best on us regardless of trends, but I think we can make small tweaks that help keep our looks modern without going overboard into trendy. Example – I have started getting my jeans with higher rises – more like 9 and 10 as opposed to 7 and 8. I’m not going to 11 and 12, though. And I like my skinnies now with a 26 or 27″ inseam (as opposed to 28 or 29 as I was wearing before) and maybe an extra inch in the leg opening to give them a slightly straighter look, but I just can’t seem to embrace the wider straight leg trend. I see stylish, fashion-forward women wearing a combination of both, so I figure I’m not out of date if I keep wearing my skinnies for a while longer.

      And with tops and sweaters – a lot of the sweaters in the after pictures were the same, I just front tucked rather than leaving them out and long. I don’t think we have to front tuck everything, as some tops are shorter now, so they work okay untucked. But with the longer ones in my closet from past years, a front tuck will extend their life for a little while longer. It worked with my body type b/c my jeans were a little shorter too, so it keeps the overall proportions in balance.

      The addition of a third piece always makes a look more complete. Shoes and bags evolve with the trends, but we can pretty much wear whatever we like, regardless of body type. And jewelry and accessories are an inexpensive way to update a look. I’ve been getting away from long pendants, for example, and layering shorter necklaces. Ditching the infinity scarves, etc. I hope that helps.

  12. Loved this post!  So helpful to see what makes an outfit look dated and what tweaks help bring the same pieces into current style.  Really interesting and informative all the way around.

    Thanks for all the effort!

  13. Really great post!  The side by side photos are so helpful when comparing. And it was good to see how little details can update an outfit and make it fresh, just by shopping your own closet.

  14. This was SO helpful. I loved the perspective on how to update outfits. I think I’ll be on the hunt for gray jeans now. I’m guessing a darker gray as opposed to a light to medium gray, right?

  15. Great post!! I love your style, and I love the time you take to explain everything (including why or why not you do certain things). Thank you!!

  16. Thank you for doing this post. It was really helpful to see the little switches you would make to keep the look current. I’m pleased to say that I have no coloured jeans in my closet, only dark wash blue or black which are higher waisted.  And, all my loose slouchy bags are donated. I still like a couple of light infinity scarves but wear mostly regular as you’ve shown. I never did get into the big blanket scarves that were all the rage for a while. They seemed to overwhelm.  Loved this post. The before & after really showed us what we should or shouldn’t be wearing in 2019/2020. 

  17. Can you do this type of post again?  It is so very helpful and while I thoroughly enjoy all of your posts, this would make my top 10 list.  Regarding the items you tried on, I so hope you keep the lovely lavender colored sweater.  It is so flattering on you in every way.  The light tie dyed sweater is so pretty.  Have a great day!

  18. This is an amazing post! I can really see and totally appreciate the small changes that bring older styles right up to date. What a help that will be!

  19. Very useful post, thank you. I like to wear my clothes for several years, at least. I mostly buy classic styles, but even with those, there are always minor changes in cuts and colours. So it’s really helpful to know how to ‘tweak’ things to stay modern. I probably do it without thinking much about it, but it’s been so helpful to actually see the thought processes that you go through. More posts like this please!

  20. Great post! It’s great the way you explained exactly what you did to update or change the older look. It’s amazing how one thing can change the whole look, the pants in #3.
    There is a lot of work in your posts and it is appreciated.

  21. Great post!  I have been looking into wardrobe capsules, so I take out of storage all my classic pieces, add a few trends, and leave the rest in storage, until those trends like slouchy purses, different types of costume jewellery, etc., come back on trend, which they always do, and the higher end items you own will still look great, and up to date when that trend walks the runway again.  It’s lighter on the wallet, and you continuously look fashionable.  You look fabulous as always!!😊

  22. What a great post!! Thanks for showing the look then and how to update now. I can see the difference. Sometimes I tell myself an outfit still looks good because I don’t know exactly what is wrong. This post will help me see more clearly how to update. Please do more of these!! Thanks!!

  23. This is such a great post.  I like to see how to wear things that may already be in my closet. There are such subtle differences.  Why waste money replacing same with same?  That’s my take away.  I have so many good clothes in my closet that I want to get years worth of wear out of and not have to replace every season.  I’m sure a lot of work went into this post.  Thank you for doing it!

  24. Late to the party here, just getting caught up on your posts (and btw, yours are the only ones I would take the time to go back and look at after the fact!). I loved this post! So very helpful! I know it was a lot of time and work. It truly demonstrates the relevance of what you do – very well, I might add – on a daily basis. Thank you!!

    PS: LOVE that pointelle sweater!! You really should keep that one.

  25. What a great post!  It is super to see how the subtle changes make things look more modern–thank you!  I too have been gravitating towards my more structured and smaller bags–I thought it was because my children are older, and I don’t need to haul so much stuff, but perhaps it has to do with updating a look too!  Thanks again.

  26. OMGoodness, this is only the second time I’m leaving a reply because usually everybody leaves posts with what I would say anyways. I’m going to repeat what everybody else said already because I really LOVED the updated posts! They were very helpful for people like me, who wonder sometimes if I’m wearing something that’s still in style or should be donated or how I can tweak them? Thanks very much and keep doing Updated posts in the future! ps: I like the side by side pics, too!

  27. Thanks, Jo-Lynne! I loved this one about the updating the old outfits. Actually, all your posts have been a lifesaver for me, since I am a bit fashion-challenged lol. I lead a busy life, and sometimes have to change quickly or at the last minute running from work to another event etc.. I used to get so stressed out, almost to the point of tears. Because of you, I can finally put outfits together quickly and that I feel good in… so thank you. I do have one question though – I have 3 blanket scarves that I love and go with several of my outfits. But are blanket scarves now considered out-dated? If yes, is there another way to wear them to make them more updated?

    1. Thanks, Karen. It means so much to hear that.

      So yeah, I think the big kerchief style blanket scarf thing is a little tired, but you could maybe cut it so it’s more oblong and tie it like a traditional scarf?

  28. I like the original and the reworked looks. That yellow cardigan is pretty. I think it’s be pretty paired with a grey or leopard t shirt too. 
    I love how you wear white jeans in your posts too. So many people are afraid of white jeans. I think they have the ability to make an outfit look fresh in the fall. 
    As always thanks for your posts. I love all the little details. They’re always enjoyable. 

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