How to Dress Up Jeans and a T-Shirt

Welcome back to 26 Days of Fall Outfits! Today is Day 8, and I’m actually planning on wearing this today. I KNOW. SHOCKER!!! This is a fall outfit you can actually wear in this crazy 90-degree heat.

26 Days of Fall Outfits: Day 8: How to Dress Up Jeans and a T-Shirt

I almost didn’t post this outfit because it seemed so simple, but I realized that that’s what most us want, isn’t it? Easy, simple outfit ideas that anyone can wear.

The key to making a t-shirt and jeans look great is good fit and fun accessories. Case in point: this gorgeous Stella & Dot Milana Tassel Necklace.

How to Dress Up Jeans and a T-Shirt

This is the kind of versatile statement piece that I love because you can dress it up or down, and it will go with so many outfits. And best of all, the tassel unclips so you can wear the beaded necklace alone. I wish I’d thought to photograph that option as well.

I chose this t-shirt because the relaxed styling is on trend, and the rust color speaks fall even though it’s lightweight enough to wear in this heat.

How to Dress Up Jeans and a T-Shirt

The cropped jeans are new — I ordered them on the Nordstrom End of Summer Sale (CLICK HERE for my list of fab finds – the sale ends on Sept 13!!)  There are only a few sizes left, so if you want a pair, I hope you’re a 31 or 32. I’m wearing my usual 29. They run pretty true to size, but they say they are “super skinny” and they definitely are. I don’t usually wear my jeans QUITE this tight, but they have a lot of stretch in them, so I think they’ll be fine.

Cropped jeans are tricky. Ankle length styles are popular, but you have to pay attention to fit, body type, and the shoe you want to wear with them. These are a bit longer than typical “ankle-length” or “cropped skinnies” and I think that’s why they work. I have a feeling that if they were shorter, my legs would look stumpy. I’m really not that good at explaining why things work, I just know if they do or not. LOL!! That is one reason why having a full-length mirror is so important.

For footwear, I could do ballet flats, of course, but I chose these embellished brown sandals because I wanted to show a fall outfit incorporating sandals. I have put my white sandals away, but these I will wear until the weather turns cold. These are super old and no longer available, but you can find tons of brown sandals on sale at Nordstrom right now, and elsewhere too, I’m sure.

How to Dress Up Jeans and a T-Shirt

Finally, let’s discuss the bag. This Waverly Petite Crossbody with grey sueded perf and softly distressed metallic vegan leather converts from full length to crossbody, to foldover crossbody, to a foldover clutch. It is also part of the new Stella & Dot Fall collection. I got it in the mail yesterday and obviously wasted no time giving it a test drive. Here it is as a full length crossbody.

How to Dress Up Jeans and a T-Shirt

And then I switched over to a foldover crossbody here, to show you the versatility. I think I like it this way the bes. You can also remove the strap altogether and carry it as a clutch. Also note — the necklace without the tassel.

How to Dress Up Jeans and a T-Shirt

Since the necklace has both silver and gold, and the sandals have both silver and gold, they grey bag works with the browns and gold in the outfit.

So that’s Day 8 — just a simple t-shirt and jeans elevated by a statement necklace and embellished sandals. Easy breezy!


Outfit Details: LOFT Vintage Broken In Tee | Hudson Jeans ‘Krista’ Super Skinny Crop Jeans (budget option) | Waverly Petite Crossbody | Milana Tassel Necklace | Tory Burch FitBit Leather Wrap Bracelet | brown sandals (options) | Kate Spade Laurie Sunnies

For more fall outfit ideas, see the Fall Fashion section of my blog. You can also visit my shop for some of my top fall fashion finds.

And don’t forget to visit Cyndi to see the cute fall outfit she’s styling today!

Join The Conversation

23 Responses

  1. Can I ask what your height is? I am looking for jeans like this but am worried that they would be too short? I am 5’5 and weigh 150lbs, I am just trying to compare as it is hard to shop for jeans online? I also normally buy a size 29 but that depends on the stretch of the jeans.


  2. I agree; most of us like a casual outfit especially if we are fortunate enough not to work anymore or work in a casual environment. I do like this outfit and the tassel necklace is so cute with it. Love the purse, but I’m with you in that I prefer it folded over. That shows more detail in the coloring. Need to get more fall colored tees. Can’t do orange but that rust is a lovely color I could probably wear. Thanks for this post.

  3. You may have answered this question before but what color and brand nail polish are you wearing? It seems like a really nice fall color and one that would go with most everything.

  4. I really like this outfit and it’s practical for me at almost 59. Since I’m retired my attire is casual, but that doesn’t mean I can’t look nice and put together. I would love to find some leopard print flats with good arch support so that I can own a pair. I just looked back at your post from day 6. Seeing how I can wear shorts on the warm/hot GA days will be very helpful.

    Have a blessed day!

  5. This outfit looks really great on you, Jo-Lynne. I like t shirts like that that are a little loose around the tummy. Thanks for sharing!

      1. I think it is supposed to! I don’t want Winter weather, but I sure wouldn’t mind a few crisp evenings where we can have the windows open and do lots of snuggling.

  6. Beautiful necklace! I like the gray handbag. I wear gray a lot, and pretty gray bags are hard to find.
    The Loft Vintage Tee is a favorite. I just ordered the new Wild Berry color. The rust color is lovely on you.

      1. My Wild Berry tee just arrived. I think this is a universal color that anyone can wear. And this tee is more opaque than some of the Loft tees – which I appreciate.

  7. Ok call me spacey. I thought you guys were actually wearing the outfits and I was wondering how it’s 95 degrees in the NE and you were south of me wearing all these cute fall clothes! Ha ha! Now I get it. That being said, this is a great everyday outfit but I can’t do any sort of pants in 90 degree weather. Definitely an outfit to save for fall. Thanks for the ideas!

    1. Haha, no, we haven’t been actually wearing each outfit. We decided to do this series in September to give people ideas and a headstart on fall shopping, but we knew it would be too hot to wear fall clothes on most days. 🙂 I do wear jeans all summer long, but yeah, it was pushing it to wear cropped jeans in 90 degrees. I work in an air conditioned house so it works. 🙂

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