Fall/Winter Fashion
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What I Wore Lately Vol. 24

As we know, all good things must come to an end, and Labor Day weekend is upon us so I guess summer is officially over. My ragweed allergy is here to prove it.

Even the weather got the memo this year. I woke up this morning to 54 degrees! I turned off the A/C and opened the windows… not the best practice for a family of ragweed allergy sufferers, but I cannot resist opening the windows on a morning like this.

So, I’m moving my What I Wore Lately feature to Saturdays during the month of September since we’re doing 22 Days of Fall Fashion on the weekdays, and here we are!

I also have my Labor Day Weekend Sale Guide for you, so don’t miss that if you’re shopping this weekend.

SIZING NOTES: I’m 5’5″ and 135 pounds-ish, with a slight hourglass shape. Unless I say otherwise, I’m wearing a 6/28 in pants/jeans, a small in tops, a 6 in dresses/jumpsuits, and size 8 shoe.

What I Wore Lately

These outfits go back about a week and a half, starting with this look that I wore to take my daughter to the dentist and then to Target for school supplies. It’s just a plain grey tee and jeans, but I love how each piece has unique details that pull the whole look together in a way that’s current and interesting.

I also added this necklace for a little whimsy. Unfortunately, I believe it’s sold out.

AllSaints tee (option) // Paige jeans (option) // Birks // Kendra Scott necklace

The next day I had an early morning doctor appointment, and I threw on another t-shirt and jeans. This time, I went with boyfriend jeans and a leopard print tee from the #NSale.

similar tee (size up) // rag & bone jeans // Birks

That brings us to Friday, and I had a workout and then a mani/pedi appointment directly afterwards. I put on a ball cap and wore workout clothes all day, and I didn’t even think to get a picture… at least, I can’t seem to find one.

Last Saturday, I spent some time to by the pool before putting myself together to do some try-ons. My suit and coverup are pretty much sold out, but I snapped a picture for some reason.

After doing a ton of try-ons and prepping for Sunday’s photo shoot, I ended up keeping this on for the rest of the day. This top looks dressy, but it’s super soft and comfortable.

cowl neck top // AG Farrah skinnies // Tory Burch sandals // Kendra Scott hoops // Gorjana star necklace

I wore this to church on Sunday, after an early morning photo shoot with Alison. I love how the rust tee gives a nod to fall, but the white jeans keep the look light and summery. You can see more of this look in yesterday’s post.

rust tee // white jeans // denim jacket // snake print mules // Kendra Scott hoops // Victoria Emerson bracelet

After church, I changed to jean shorts and a tank for the afternoon. I took a nap and read a book by the pool, which sounds glorious, but I was nursing a stiff neck so I was really just trying to distract myself to get through the day.

similar tank // similar shorts // Birks

On Monday, I had some errands to run, and I was feeling inspired by my 10 ways to wear joggers post. Sorry for the cloudy picture; I didn’t realize I had sludge all over my iPhone camera lens.

grey tee (size up) // denim jacket // Vuori joggers (size up) // P448 sneakers

I was pretty lazy on Tuesday. I had a workout in the morning, and I worked from home the rest of the day. It was grey and cloudy, and I wasn’t feeling super motivated, but eventually I changed into a t-shirt and jeans.

This tie dye tee is really fun, but definitely size up. I’m in the medium, and it just fits.

tie dye tee (size up) // rag & bone skinnies // Birks // Lucky Brand earrings

Later on, I decided I was too chilly for short sleeves, so changed into this hoodie. It is so ridiculously soft, I can’t even tell you. It’s spendy, but it’s 10% off right now… every little bit helps, right?

Z Supply camo hoodie // rag & bone skinnies // Birks // Lucky Brand earrings

I had PT on Wednesday, so I wore joggers and a performance tee. I brought a lightweight sweatshirt along because I always get cold in the PT office. It’s an old Zella hoodie that I love because it’s super soft and lightweight.

Then I ran into the grocery store on my way home, where I was spotted by a Instagram follower… that was fun! I had been planning to change into real clothes when I got home, but I figured I already saw people and got recognized from my blog, so I might as well just be comfy for the rest of the day.

hoodie (old) // Athleta top (Volcanic Violet) // Lululemon joggers // Birk Madrid

That brings us to Thursday… I had a workout in the morning, and I hosted a few ladies for a book club that night.

This is the Everlane pima micro rib cap sleeve tee from last spring. I don’t wear it a ton because it’s so body-con, but these jeans have a higher rise that smooths things out, plus the straight cut helps balance out my shoulders and hips, so it turned out to be a good pairing.

I added a few bold accessories to dress up this simple black tee and white jeans. I keep forgetting I have these earrings… I really like how they show up in my dark hair, and they have a pleasing contrast against the black top.

I also wore a Victoria Emerson wrap bracelet — this is the sunrise dorado on ivory-cream.

Everlane tee (size up; wearing M) // Levi’s 724 straight crops (also at Revolve) // similar sandals // geo hoop earrings // wrap bracelet

Yesterday I took my daughter to the high school to find her classrooms. School is starting out virtual, but they’re acting like they may be in the building at some point this fall… we shall see!

Does anyone else collect water glasses in their bedroom? 😂 I take one up with me every night because I like to have water by my bed if I wake up thirsty, and also to take my thyroid meds first thing in the morning. Sometimes I absentmindedly take another one up during the day and forget to bring it back down with me.

I usually end up with a collection on my bedside table and on my bathroom sink, so I grabbed these to take them downstairs yesterday and they were in my hands when I went to take my outfit picture.

Of course, I put them down on the ironing board so I could get a proper photo… and promptly forgot about them and went downstairs without them! I give up.

I also picked up some new face masks… isn’t this print so pretty for fall? (This is not a political statement; they’re required in public places here in PA. If I have to wear one, it might as well be cute.)

Sanctuary tee (also at Zappo’s) // rag & bone Cate // Tory Burch sandals // LOFT stretch bracelets // Lucky Brand earrings // Gorjana super star necklace // Sanctuary fashion face mask

And finally… evolution of an outfit, coming atcha!

We went out to dinner last night with Paul’s brother and SIL, so I laid out a bunch of options on my bed…

I had it in my head I wanted to wear this jacket. I picked it up on sale last spring, and I haven’t had a chance to wear it.

This is the look I was hoping would work… I like the combination of the jacket with this leopard blouse, since it has some of the same greige going on. (The leopard print blouse is a few years old, so I don’t have a link.)

I thought the light grey jacket would work better with off-black jeans than a pure black, and I like how these sandals bring together all the neutral tones in the outfit… but something about the finished look wasn’t setting quite right with me

Here’s the look without the jacket. Assuming I wouldn’t need the jacket the entire time, I wanted to be sure I liked the look okay without it. It’s okay, but the jeans look too casual or something.

I decided to try my black Chelsea28 raw edge tank… sometimes I just prefer the simplicity of solids.

But I definitely didn’t like the harsh contrast of the black top against the light grey jacket, and the jeans still look a bit ragged to me.

So then, I thought, what about my taupe moto? It’s more casual, in a way, and there’s a lower contrast against the black top.

The color combo is better, but the jacket is just too heavy for this time of year, and the sandals definitely looked out of place with this one.

So then I went back to the first look, and I pushed up my sleeves and added jewelry. You can’t see my earrings, but I was wearing these Kendra Scott drop earrings, and my favorite Victoria Emerson boho cuff.

I kept looking at it, but I couldn’t love it. Caroline was hanging out with me, and she said the sandals just don’t look right with it, and she also didn’t care for the length of the jeans.

I agreed, I would prefer a longer pair, but I thought pure black would be too harsh against the light jacket/top combo and the sandals.

I thought maybe a change of sandal would do the trick, so I put on these black ankle strap sandals that are often my go-to when I want a dressy but comfortable sandal. I knew we’d potentially be doing some walking downtown.

The pants still looked short to me, and I couldn’t get excited about it.

FYI, these Stuart Weitzman sandals are 47% off! I have them in both beige and black, and I fall back on them all the time. They’re gorgeous and comfortable and classic and go with everything from dresses to jeans.

This picture is from years ago, but it gives you a close-up.

Stuart Weitzman NearlyNude Block Heel Sandals in Black Nappa

So back to the outfit… I even tried beige pumps, which I like a little better than the sandal options, but I knew I wouldn’t want to walk in those. Plus, I don’t love the warm beige against the cool tones in the outfit.

Caroline said I needed booties, and I tried two pairs that sort of worked, but the look got really heavy for Labor Day weekend.

I also tried the sandals look with these black jeans, but as anticipated, they were too dark for the rest of the look. I didn’t take pictures of those options because I was out of time.

Now that I’m looking back at all these pictures, I think it’s the raw hem off-black jeans that are throwing off the look. They’re just too casual for the blazer/leopard blouse combo, and don’t really work with the sandals either… ya think?

By then, I was running late, so you know what I did?

I threw on this outfit that I wore out to dinner with a friend a couple weeks ago. You may remember I did a similarly lengthy try-on sesh that night, and ended up wearing something totally different than what I was originally going for.

I don’t know if this is really a better choice than my original outfit, but sometimes, you just gotta go with what feels right to you and stop second guessing everything. I will almost always err on the side of comfort and familiarity, even if it means my outfits are repetitive.

This denim jacket + printed blouse + black jeans + ankle strap sandals is a date night outfit formula that has worked for me time and time again, and if it ain’t broke, why try and fix it?

Halogen blouse // Kut from the Kloth Donna skinnies // Stuart Weitzman sandals (similar for less) // Vince Camuto denim jacket (on sale!) // Kendra Scott earrings // Stella & Dot bracelet

At any rate, that’s a wrap!

I hope you have an awesome weekend. I’ll definitely be outside enjoying this glorious weather.

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30 thoughts on “What I Wore Lately Vol. 24

  1. Ad my mom always said, “If it ain’t broke, don’t fix it!”  I like what you ended up wearing!  Don’t you have a pair of light washed black jeans?  I bet they would have looked good with the animal print top and jacket.  I’m so jealous of your temp in the 50’s this morning.  Our low was in the 70’s with night humidity, with the high going up in the upper 90’s again.  I’m ready to not have to keep the curtains drawn to keep some of the heat out.  I hope y’all have an awesome day and long weekend!

  2. My bed doesn’t look like that when I start getting ready to go out but sometimes it ends up looking like that! Then I have to hurriedly put everything away before I go out the door. I love reading your anatomy of an outfit posts. Enjoy your long weekend!

  3. i loved the trial and error portion of this post. It just goes to show you can be gorgeous, have wonderful individual pieces of clothes, but they sometimes just don’t click – I call it “trying too hard.” Caroline has good instincts – I think it definitely was the jeans and shoe combo that was all wonky. You do such a great job, Jo-Lynn – keep up the good work.

  4. Question about your All Saints Grey tee. The model on the website is wearing a medium (and she’s not very busty.) what size are you wearing?  I need a new gray tee and like the style of that one a lot. 
    Your denim jacket to the rescue! 😁 (I actually liked your first date night outfit’s top and jacket combo, but yeah, the jeans kinda threw off the look.) I’m jealous of you going out to restaurants and having a somewhat “normal” life again. I actually went into Sephora yesterday (they just reopened their store next door to our local Whole Foods) and I realized it was only the 2nd time I’d been in a retail store since the pandemic shut down began  in March! 

    We’re in the midst of our CA summer heatwave,  so the air conditioning had been working overtime. Three years ago we got solar panels so our electricity bill is mere pennies, but yet we’re still included in the power company’s planned “rolling blackouts” this weekend. 🙄 Do other states do this or is just Cali? Fortunately we’re close to the beach so our temps won’t reach triple digits like they do inland. I’m heading out for a walk before it gets too hot. Have a great day! 

    1. The tee is a small – I know, I noticed the model was wearing a M as well. I guess I just don’t like my tees as drapey. I think drapey looks better when you’re smaller on top, and super skinny.

      There are no rolling blackouts in PA… that sounds crazy to me.

      I am so grateful we are able to be out and about. I assume it’s b/c we were shut down for so long, and then opened gradually, and always had mask laws. But who knows…

      1. Thank you- I will order a small. I’m wearing a lot of t-shirts and jeans/joggers/ shorts these days working from home. 
        And yes, the rolling blackouts are ridiculous. I’m a Cali girl through and through, but I’m NOT a fan of our Governor. But that’s a topic and a rant for a different blog. 😏🤪

  5. I love these outfit evolutions and definitely relate to bed pile. Thanks for validating my quirks. The problematic jeans look to have a blue undertone to the gray.  It’s strong in the photos but perhaps not so much in reality.  They do throw off the outfit.  I have same jacket, similar top and pair with dark gray Levi skinnies & reptile cage booties/sandals(?)  It’s cute.  Yesterday I saw a pic of Sarah Jessica Parker wearing gray crop flare jeans and lighter gray denim shirt, strappy slides. So chic!  Typically not a fan of that style jean but thought of you and your green crops from the other day. Look for the pic, it’s taken from behind at grand opening of her NYC shoe store. 

  6. Love the jacket with that leopard blouse! I bought the same jacket in early Spring to wear for Easter and haven’t worn it yet either, lol.

  7. I always enjoy seeing what you have really worn. For some reason, when I see your off black jeans on my phone, they look blue. I don’t know what is causing that, but I have to wonder if your eye is seeing them as blue also?  Do they look blue in your phone, or is it just me?  

  8. Always love the outfits you put together!!  My question is what book your book club ladies read and discussed?  Always looking for a new read.  Just finished another Mary Alice Monroe novel…LOVE her books!!!

  9. Yes I do that !,,, When I had events and places to go to!,,
    Now once again numbers here kind going up:(
    I think the jeans were taking away from the nice shirt and
    Jacket.  I’m still not used to the ankle cut off look.
    Enjoy your beautiful weather this weekend!

  10. You are selling yourself short about cropped flairs. The look really good on you and would have lookEd great with the leopard & jacket combo.  I would have worn white or black cropped flairs.I agree that something about those jeans was throwing the outfit off.  Keep the posts coming, I look so forward to them!

  11. Sooo confusedabiut the “ off black” jeans. They look to me like plain old blue jeans. Is there something about the lighting that messed this up? 

  12. Oh my goodness! Thank you for showing us what exactly wasn’t working with the outfit. I can’t tell you how many times this has happened to me. It helped that are you breaking it down and showing us more options. Loved the outfit that you actually wore.
    Thanks again,

  13. I love reading your evolution of an outfit posts as well – very informational, with small details that can make a big difference. Thank you!

  14. Yep. The jeans were the problem from the beginning. I’m surprised you didn’t try any blue jeans that were the correct length and not ragged.
    You looked nice in the end, and that’s what matters, right?

      1. I watch water color tutorials with Sarah Cray from Lets Make Art and she’s always telling us that our head gets us into trouble. It makes us doubt what our eye are saying is correct.
        Get out of your head! 🙂

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