Fall/Winter Fashion
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Plaid Shirt Outfit

Hello, friends! I hope y’all are enjoying your long weekend. I’m back today with a fall plaid shirt outfit for Day 4 of 26 Days of Fall Fashion.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

There’s actually a chill in the air here in Philly this morning, and when we were hanging out on a friend’s patio last night, I was wearing an outfit quite similar to this because it cooled off after the sun went down. I love it! Warm days, chilly nights… yes please!

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

Before we get to the plaid shirt, let’s discuss these jeans. I am so excited to be able to recommend a pair of jeans that are priced well under $100. I KNOW. Don’t faint on me here. I’ve spent so many years singing the praises of premium denim, and I stand by it, but I also know that you guys like it when I find more budget-friendly products to recommend, so I set out to find a pair of jeans that fit the bill.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

These Wit & Wisdom ‘Ab Solution’ Stretch Skinny Jeans retail for $68, and they get excellent reviews on the Nordstrom website. I ordered them after I saw another fashion blogger wearing them, and I’m impressed with the fit, quality, and comfort of these jeans.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

These have a comfortable 9 1/4″ front rise with a 30″ inseam and a 10″ leg opening. The Ab Solution power-mesh panels slim and hold, and the waistband has interior control and booty-lift construction. I’m all for the booty-lift and waist control!!! What woman in her 40s can’t use a little bit of that!?!

They remind me a lot of my beloved DL1961 Emma skinnies — the wash is similar to the pair I have, and the fit and feel is similar as well. They have a lot of stretch to them, which makes them super comfortable to move around in. For size reference, I’m wearing the 8.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

I topped the jeans with my favorite white tee and a plaid button down.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

This is a new look for me. I am not generally drawn to plaid or button-down shirts, for that matter. But I wanted to step outside of my comfort zone and give it a try.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

I have heard amazing things about the Rails brand, and I’ve seen them in the store because there’s often a rack of them near the premium denim. One of the reasons I tend to shy away from this style top is they are usually thick and kind of stiff, but this fabric is soft and thin like pajamas. It’s really amazing, and yes, priced to match, but they do go on sale from time to time.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

The fun thing about a plaid button-down is you can wear it so many ways. Wear it buttoned up and tucked in or out, wear it over a tee and open in the front, or tie it around your waist. I’ve also seen them worn open over casual dresses, and that’s a cute look.

Tie a plaid shirt around your waist for a fun weekend casual look!

Because the shirt has a masculine cut to it, I intentionally chose a plaid in feminine colors.

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans

To keep the outfit ultra casual, I wore my Chuck Taylor Shoreline sneakers. I get a lot of questions about these. People often tell me they want a pair of Chucks, but when they try them on, they feel like their feet look like boats. I know what you mean. I tried these on about 10 times before I finally bought a pair!

The Shoreline style definitely helps them look less like boats, but they still take some getting used to. Just remember, no one is looking down on them the way you are. I love that I can just slip these on and go without futzing with laces.

I don’t wear socks with mine, but if that bothers you, you can always wear a no show sock. In fact, I just ordered a pair. And before you ask, yes, you can wear these shoes all year round. White canvas shoes aren’t just for summer anymore.

Loving these Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom for $68!

This cognac crossbody is in keeping with the cool, casual vibe of this weekend outfit, and at $49, it won’t break the bank. I layered two necklaces and added a small stack of Alex and Ani bangles to complete the look.

Accessorize your casual fall outfit with this affordable BP. Faux Leather Saddle Crossbody Bag from Nordstrom!

I’d love to get your thoughts on this outfit! How did I do styling my first plaid button-down???

Styling a casual fall plaid shirt outfit for a fun weekend look featuring the Rails Hunter Plaid Shirt and Wit & Wisdom Ab Solution Stretch Skinny Jeans from Nordstrom.

 

plaid shirt // white tee // skinnies // Converse Shoreline sneakers // initial pendant // bar necklace // sunnies // Alex and Ani bangles

Be sure to visit Cyndi and see the fall outfit she’s styling today!

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41 thoughts on “Plaid Shirt Outfit

  1. Well, I know you’re typically not one for collars and button downs – or plaid, but this.. I just love on you. You should definitely keep this kind of look in rotation! You look comfortable in it, like you’ve always been wearing it. I personally have always loved plaid tops and can’t seem to get enough. I probably wear them like this most. There’s just something about plaid, jeans, and converse that I adore. And this particular top is gorgeous! I doubt I’ll ever have one in my closet, but I’ve noticed this brand always has THE best look. Love it!

  2. Just curious if you’ve washed your Shorelines? I wore mine this weekend to a football game and got them a little muddy water spotted.

  3. You’ve inspired me to do another purge in my closet as well, and set aside my summer stuff today 🙂 I think you look fabulous in the plaid, comfortable yet pulled together and stylish….thanks for all the inspiration

  4. Love Wit and Wisdom and love plaid and I am very feminine. I also bought Chucks shoreline for the first time a few months back! Enjoying this look on you.

  5. I love this look on you! This is my go to look in the fall and winter, when I’m not wearing a cozy sweater!! Just don’t think you can go wrong with jeans and plaid – even better when you add boots!! ????

  6. I love everything about this outfit!! Yesterday my youngest daughter walked out of the house with a cute tan suede skirt, black T, black Converse and a plaid shirt tied around her waist. We were headed to Church. I thought that is the cutest outfit. I wish I could dress like that. Thank you so much for giving me the option to wear something as cute and casual and not feel like I’m dressing too young for my age!

  7. Your shirt is currently 40% off. I love the look in you and am inspired to give it a try. I have all the other pieces, just need a feminine plaid!

  8. You look great in this look! I think the relaxed plaid is flowy and flattering. I have one in short sleeve, I still hope to layer this fall. Too, your plaid top will go with many shades of blue jeans, and I’d even pair it with white pants. As a matter of fact, I just wore my plaid top, blue jeans, and white converse to a 6th grade field trip on Friday. I think the whole outfit is a classic????. Thanks for the tips on organizing closets from summer to fall…I will try to purge and put in storage????. Hugs, Marti.

  9. Btw, I just looked up the plaid top online. I noticed a sleeveless, longer length plaid top too. I’d be curious how you style different lengths, and sleeveless plaids entering into fall. Suppose, you just treat it like a jacket/layer?? Thanks!

  10. I REALLY like this outfit on you. I know it’s a bit of a departure for you, but hey, if you can gently nudge all of us out of our comfort zones, you have to do the same for yourself, right? <3 Those jeans look to be right up my alley. I just bought a pair of gf ankle jeans from Gap, (hoping they'll be a little like bf jeans, but not too sloppy), so I'll have to budget yours in for later. But YES and AMEN to the tummy control and butt lifting. xo

  11. Hey Jo-Lynne,
    I’ve been a silent reader this summer, sorry. I’ve had no childcare for the summer so very little time and slightly going nuts, as much as I love them! ????
    Anyhow, this look is fab on you. The shirt colours are beautiful. It’s funny because last weekend when I finally had 2 hours to myself, which I decided to use for much needed retail therapy, I finally bought a plaid shirt myself! I had always stayed away from the look as I felt I was wearing a kitchen towel. But when I put it on I liked it, even my mum liked it, who is not into anything a bit masculine. M shirt is a tunic style, burgundy and navy, not really plaid, more like big squares, if you know what I mean? I love it, as it can be worn with skinnies, leggings, maybe even bare legs if I dare. And I hadn’t thought of wearing it open and layering, that’s a good idea!
    Anyhow, can’t wait to see more of your fall fashion. X

  12. Fantastic as always. And thanks for discussing the Wit and Wisdom jeans. Been looking for a more reasonably priced Jean and Nordstom here in St. Louis carries this brand. I will be on my way for a try on ASAP. Thanks JoLynne

  13. What a great outfit Jolynneshane! I’m looking forward to copying it ❤️. Do you have a recommendation for skinny ankle jeans for petites? At 5’2″, I struggle to locate a pair (that doesn’t need altering) that hits the ankle at the right spot.

    1. Have you checked LOFT? They carry a great selection of Petites. If you want premium denim, altering them is worth the investment. I follow a petite fashion blogger that wears the Paige Verdugo ankle jeans, and she mentioned that she had them hemmed and narrowed a bit to keep the right shape. Nordstrom has free alterations if you have a Nordstrom card.

  14. Love those jeans on you! I have a pair of Wit and Wisdom skinny jeans that are not ab solution and I feel like the fabric is a little thin and clingy on my thighs. Would you say the ab solution jeans are more substantial? Do they stretch as you wear them?

  15. This is super cute! I love those jeans, I have a few pairs myself and they are comfy. And I love the plaid! I have a plaid shirt I love and I think I’ll copy this look!

  16. All I have to say is that you nailed it with the plaid. It looks casal , comfortable, but it in no way looks like you are heading to a barn raising (and even if you were, you’d be the Belle of the ball). I am usually not a plaid shirt girl myself, but I think with your accessories and shoe selection

  17. I just bought a pair of black Ab solution from N Rack on Friday. They are the first pair in a very long time that actually look good from the back, and that is not an easy task as I’m nearing my mid 50’s. No pulling under the fanny and even fit nice behind the knee. I’m going to definitely try the jeans.

  18. I’m a little late on commenting, but I love your hair! It makes you look younger!! How did you style it?! The outfit is cute too!!

  19. I know this is an old post but do you like your Wit and Wisdom Jeans? I just got them in the mail and I’m not sure if I like them. You don’t seem to wear them very much. I’ve bought quite a few of the jeans you wear and love them.

    Thanks,
    Toni

    1. Hi Toni. I think they’re a great pair of jeans for the price point, but I don’t like them as much as my premium denim brands, so I don’t wear them very much. Personally, I’d rather wait for a sale and pay $100-130 for AG or DL or Paige and have fewer pairs, but I also know that not everyone can stomach dropping that much on a pair of jeans, so the Wit & Wisdom is a nice choice in that price point.

  20. Looks fabulous!
    Would you mind sharing the size of your t-shirt? The site says they run large and suggests sizing down.
    Thanks!

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