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How to Dress Super Casual but Look Pulled Together

February 1, 2022

Hello and welcome to Dressed for My Day. Since my goal here is to help us over-50 ladies get dressed for our unique days so we can show up in a big way, I have to acknowledge that some days just call for super casual attire. Whether you’re joining the grandkids for a hike, standing on the sidelines at their soccer game or venturing out to a flea market with friends, some days we simply don’t want to wear our best things. But we can still look cute! Today let’s talk about how to dress super casual but still look pulled together.

Super Casual but Pulled Together
flannel shirt // grey jeans (curvy fit) // boots // scarf (similar, slightly more economical) // simple hoop earrings // puffer coat // beanie

Tip #1 – Pull together the colors in your outfit.

In other words, match. No, you don’t have to match completely. But we can still put in a little effort and pull together an outfit that coordinates colorwise. The best way to make that happen consistently is to build a wardrobe around a scaled down color palette. I advocate putting together a wardrobe that only consists (at least initially) of two to three neutrals and three to five signature colors.

Want to know more about how to picking the colors of your wardrobe? Check out this post, How to Choose the Colors of Your Wardrobe.

Look Pulled Together

Tip #2 – Make sure your clothes fit properly.

You might think this (and some of these other tips) goes without saying. But I’ve been guilty of holding onto things that don’t really fit anymore, and I bet you may have, too. Then we relegate those clothes to a category that we’ll wear when we’re not doing anything special or we might get a little messy. But really, if we want to look pulled together even on those casual days and outings, we need to wear clothing that fits.

Want to know more about how your clothing should fit? Check out this popular post, 9 Signs Your Clothes Don’t Fit and How to Fix That.

Opt for Tailored Clothing that Is Still Comfortable

Tip #3 – Wear at least one tailored piece of clothing.

While the day may call for comfort and/or warmth, we can still wear at least one piece of tailored clothing. That touch of tailoring will elevate your style quotient considerably. So in today’s outfit of grey jeans and flannel shirt, I’ve chosen to wear a slightly tailored flannel shirt instead of the boxier, looser fitting one. This is the kind of style choice that might be important if you’re scouring flea markets but then you plan to stop into a nice café for lunch or coffee. No, you don’t have to look nice to eat in a café. Hahaha! But maybe you just want to look a little nicer than a lumberjack.

Wear a Little Makeup
flannel shirt // grey jeans (curvy fit) // boots // scarf (similar, slightly more economical) // simple hoop earrings // puffer coat // beanie

Tip #4 – Wear a little makeup and do your hair.

Look, I really don’t mean to talk down to my sweet community here. Let’s just say I’m preaching to myself! I’ll confess to sometimes skipping the makeup and hair just because the day is going to be super casual. But if I’ll take just a few minutes to define my brows, add some tinted sunscreen, swipe on a couple of coats of mascara and apply a lip gloss, I’ll feel so much better about myself.

Wear Some Earrings
flannel shirt // grey jeans (curvy fit) // boots // scarf (similar, slightly more economical) // simple hoop earrings // puffer coat // beanie

Tip #5 – Add a piece of jewelry.

Indeed, there are some days and outings that make wearing jewelry a silly notion. My casual outfit that I’m wearing here would look out of whack with the combination of necklace, earrings, bracelet and watch that I generally wear. So I took most of the jewelry off that I’d had on for another outfit photo shoot, and kept on just my simple hoop earrings and necklace. I could have even removed the necklace, if needed.

Just that touch of jewelry not only adds light around my face, but it also indicates that I took a little time to add a finishing touch. And that finishing touch comes across as polished and chic to the beholding eye.

Put Some Thought Into Your Accessories
flannel shirt // grey jeans (curvy fit) // boots // scarf (similar, slightly more economical) // simple hoop earrings // puffer coat // beanie

Tip #6 – Put a little thought into your outerwear and accessories.

Just because the outing is casual doesn’t mean we have to jeopardize our appearance by adding an ugly coat or mismatched accessories. That’s why I buy most of my winter outerwear and accessories in neutrals that mix and match easily. And if nothing else, just having a beanie and scarf in coordinating neutrals will help keep your outfit looking pulled together and a little polished. (I think I accidentally left my grey gloves at home on this day!)

Remember, when we’re out and about, especially in these super casual situations, many people will only see us with our outerwear on. So it’s smart to purchase outerwear that will add value to a variety of our outfits rather than detracting from them.

Casual but Pulled Together

Truth be told, I realized I’d just posted an outfit with a flannel shirt a couple of weeks ago, and I didn’t want to just repeat myself here. When I set out to cover a topic (like flannel shirts) at the request of readers, I tend to order several iterations. The last post featured a more economical flannel shirt (although both are from Target) layered for a really fun look. But of course it’s casual, too. Anyhow, I hope you’ve enjoyed today’s post about ways to dress super casual but still look pulled together. I know it’s pressed me to think about how I compose these types of outfits myself.

You can shop this outfit through the links above or through the shopping widget below. Let me know if you have any questions. I’m so grateful that you’ve stopped in. Have a blessed and lovely day!

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Blessed for My Day

Love is a choice. Some days it’s an act of the will. If we wait for the feelings to surface, we may neglect to love well. Instead, we become more self-focused and apathetic toward the one we say we love. Indeed, some days we must act out of love well before we feel any warm and fuzzy emotions.

Believe it or not, the same is true of our love for God. The best way we can continue to reserve room in our hearts for the God who loves us so much is to actively love Him. We must choose to show Him love even when the emotions may wane. How can we love God with all our of heart, soul and strength? By obeying Him even when it goes contrary to our want-to’s, by worshiping Him with spoken or written words of praise, by spending time with Him in prayer and Bible reading and by telling others about what He is doing in our life.

Hear, O Israel: The Lord our God, the Lord is one. Love the Lord your God with all your heart and with all your soul and with all your strength. ~ Deuteronomy 6:4-5

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xoxo, Kay
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19 thoughts on “How to Dress Super Casual but Look Pulled Together

  1. Great post! Yes, I can be over-casual at times, but it’s those details that you suggest that elevate the look. I never thought about it. Thanks for pointing these out. Keep up the great work!

  2. This post spoke to me. I am retired and living in Northern Michigan. Most of my days are very casual. I want to dress appropriately for the day’s activities but not look like I don’t care. These suggestions make a lot of sense and give me something to work on. Thanks!

  3. You pulled together a really good casual outfit today ?. I have but one flannel shirt that I should pull out more often. We are having blizzard conditions today that calls for a casual but warm outfit! Thank you Kay, as always you’re inspirational ? Blessings sister, have a great day ❤

  4. I got kind of causal yesterday. Had to run errands. Just go to the store, bank, and tabs for my car. I just wore a nice pair of jeans and sweater layered over white blouse. It was not to cool, so I put on a vest in hot pink to match the gray and pink sweater and added a pink scarf and gloves. I love Talbots for these looks. You are so right, the right accessories can elevated the look even though you chose to dress casual that day. You also look pulled together in your outfit you posted, though I do not do plaid blouses, that seem all the rage now. I’m more of a sweater girl. ha Loved the BFMD. Right on. Bless you.

  5. Does this mean I should leave my Fanny pack at home?? All good tips and since I’m rural, I do see a lot of flannel shirts here on the Coast because we just don’t get that cold and it’s hard to beat a flannel shirt, jeans and boots. That can look a little too casual though if we head into our small town so a little glam couldn’t hurt. Someone is bound to tell me I clean up nice though if I try too hard. ?

  6. Love it! Been researching how to dress for our trip to Italy this spring. I’ve seen a few articles mention that the Europeans don’t wear workout gear (outside the gym) like we do here. I’ve been more mindful, as a result, of not doing that here at home. I’m wearing jeans and cords more on those casual more joggers outside the gym.
    Love those grey boots! Would have bought those had I not already recently purchased some grey suede ones. Mine aren’t water resistant though.

  7. Hi Kay! Loved these tips to step up our casual outfits! One question, what size are you wearing in the Talbots grey jeans (mostly sold out, I see)? I usually don’t purchase the Curvy style, a regular size 10 is perfect on me. Is the Curvy fit a little more relaxed around hips and thighs? Another favorite Blogger, JS, highlighted grey jeans today as well!! Great ideas!

    1. Hi Sue. They run true to size. I’m wearing an 8. The fit difference between the regular and curvy is quite subtle in my opinion. That said, I have the curvy in the regular straight leg jeans and really wish I didn’t. They’re just too roomy on me. But yes, the curvy are slightly more roomy in the hips.

  8. This post was great! Most of my life is spent in casual clothes and these tips for taking them up a notch is just what I needed. Thanks Kay,!

  9. Because of my work and life style casual is my daily outfit. Thank you for the tips. I enjoyed coffee time with you yesterday

  10. Kay, I really like this outfit! It is so pulled together. Grey is one of my neutral colours and I never thought of buying grey boots. They match the colour of your jeans and make your legs so long!
    Yesterday, I came “late to the party” so I didn’t add a comment, but I do want to mention how much I enjoyed “Coffee with Kay”. Wonderful way for us to feel personally connected to you. You were asking us for ideas in regards to your blog facelift. I was wondering if your Blessed For My Day posts could be saved, separately, for subscribers to easily find at a later date? Thanks for your consideration on this idea.

  11. A great post today Kay! It truly resonates ! I must be careful bit to look overly casual sometimes (messy/not coordinated). I found the right scarf to go with all of my winter coats so that will help!
    Hoping your skin treatment goes smoothly and will pray.

  12. Thanks Kay for being so real!! I’m born a big city gal, but we live in New Mexico now, with horses, dogs, etc., I love to hike, garden, and have a wild grandboy, so my days are always about how to look “slightly pulled together ” while doing the the things I love! Work involves a construction site, I get dirty, pick up animal hair, sweat in embarrassing places, have had dust and sunscreen in my eyes to where I’ve had to hose my face, to also avoid heat stroke. So I’m with you on trying to look a bit (you think?) pulled together in spite of what a casual day brings!! LOL! I try to buy good quality basics in the most beautiful colors, wear updated outdoor performance brands, and never save the “tired” clothing for even the garden, that is my happy place, sometimes I even wear a dress when I’m thru with the hard work! Thanks again and keep up the good work Kay, your spirit shines through!

    1. Ooh, thanks so much for sharing Laura. It turns out I have quite a few readers in similar lifestyles evidently. And I love it! Women can do hard things and get messy! Thanks so much for sharing this perspective. ?

  13. This is my real life and how I dress most of the time. I live in the Catskill mountains on NY and am an outdoor girl. Yes we can look pulled together even as mountain women!!

  14. Like many women, I watch multiple influencers and choose what I like from each to try. This morning, I watched a video done by a stylist who was talking about plaid shirts, classic button down shirts, being too classically casual. Wearing black around the face is a no no. I pressed the unsubscribe. Kay, I like the way you are all over with what you wear. Unless women are in the work force, we live in a casual mode but yet want to be a standout for looking put together.

  15. LOVE this post. I have always been a casual girl since I was a home school mom. I had a more fancy wardrobe for church and other outings.

    We have always been involved in our worship department at each church we attended, a very visible ministry. I learned early on that I never knew when I went out if I would see someone who might recognize me from church. I always wanted to be dressed in a way that was honoring to God and our church.

    Yesterday, I came “late to the party” so I didn’t add a comment, but I do want to mention how much I enjoyed “Coffee with Kay”. Wonderful way for us to feel personally connected to you.