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Winter Classics Outfit with a Chambray Shirt and Wool Pants

February 8, 2021

Happy Monday! It’s frigid cold here in Ohio, and this Southern girl is learning the value of warm clothing. But whether you live in a cold climate or your area is warmer, I hope you’ll enjoy today’s winter classics outfit. If nothing else, it’s a reminder of how a classic chambray shirt can change up an outfit and make it more casual but still polished.

Winter Classics Outfit with Chambray Shirt
Donegal tweed trousers //

I had a request from a loyal reader to share some more casual ways to wear wool trousers. So today I’m restyling my Donegal tweed trousers with a slightly more laid back vibe. In this recent post I wore these same wool blend trousers with a cashmere sweater and red suede pumps.

Donegal Tweed Trousers

Talbots has marked these Donegal tweed trousers down from $129 to just $39.99, and they’re still available in most misses sizes. I’m wearing my usual size 8. Unfortunately they’re no longer available in their petite or plus sizes. But you can recreate this polished but casual look with any other wool or wool blend pants in your closet.

Donegal Tweed Trousers

The real key to this look is the chambray shirt. I find that a chambray shirt is a must-have in my closet. It’s that shirt I reach for when I want to “button up,” but I still want to look more laid back. This is such a versatile piece. It adds polish to a pair of white jeans or khaki pants. But it creates a more casual look with these tweed pants. Plus, I just love the blend of denim and tweed.

Denim Shirt

The denim shirt I’m actually wearing is this one, and it’s marked way down. But it’s only available in one petite size. But Talbots’ newest chambray shirt looks just like this one and they’ll undoubtedly have it available for a sale price soon. I’m wearing a true to size medium.

If you’d like to see more ways to style this workhorse, you might want to check out my post, 13 Reasons You Need a Chambray Shirt in Your Closet. It’s an old post, and most of the links are out of date, so I’ll probably update it this spring. But for now you can at least see a lot of great ways to wear this versatile shirt.

J. Crew has their chambray shirts marked down as much as 50% today. And this one at Gap has a slightly more western vibe, but it’s still quite classic.

Camel Blazer

I topped my wool blend pants and chambray shirt with a classic camel blazer. But another fun option would have been to wear a denim jacket if you’d like to go even more casual. In fact, maybe I’ll do that for another look with these pants. (I recently picked up this ultra soft and slightly fitted denim jacket for 40% off the regular price.)

Camel Blazer

I’m also finding this camel blazer to be very versatile. You may remember seeing me wear it in last week’s How I Really Dressed for My Day, where I paired it with jeans and a sweater. I purchased the blazer when it was 50% off, but unfortunately it’s not marked down at all right now.

DFMD Insiders’ Tip: You can “favorite” items in the shopping widget below to receive an alert when they go on sale. Just click on the heart under the item. You may be instructed to then set up an account if you don’t have one. But it’s safe and non-intrusive in my experience.


I think this winter classics outfit would appear even more casual if I’d worn different shoes. But the thing about pants is that you have to have them hemmed to the length that’s appropriate for the shoes you’ll wear them with. And I want to be able to wear my Donegal tweed trousers with heels for the most part. So I wore my brown suede Jayla boots. They’re no longer available in brown, and only available in black in a few sizes. But they are marked down significantly. These are very comfortable and versatile boots and fit true to size.

A few of the style choices I made with this outfit include tucking my shirt, belting my pants with a 1″ brown belt and wearing minimal jewelry. I reach for the Halogen teardrop earrings so often. I like that they’re big enough to have an impact, but they’re simple and very lightweight. They’re also available in brushed silver.

Wool Blend Pants with Chambray Shirt

I would have loved to have styled these wool blend pants with white sneakers, honestly. But they’re too long for that. But I think I’m up for styling them with my black wedge sneakers for an even more casual look. Would you like to see that? I enjoy styling classic pieces like these pants multiple ways.

Shop the Post:

You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

Thanks so much for dropping in for today’s winter classics outfit. If you’d like to see more of my winter classics outfits, check out these:

And if you have a request for a winter classics outfit with a particular winter closet classic staple, let me know. I’ll see what I can do!

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Blessed for My Day

The Bible assures me that love never fails. But honestly, sometimes it feels like love does indeed fail. Sometimes we feel like we’ve loved and forgiven and given grace and prayed and been kind and…still, nothing changes. The relationship stays hard. The circumstance feels difficult. The environment doesn’t get better.

I think that’s because we fail to remember that love must keep on loving. Love must endure. Real love stays the course, presses on. That’s not to say that love has to be soft, mind you. Pressing on in love doesn’t mean you have to put yourself in jeopardy or give in to abuse. That’s not real love anyhow. Sometimes love is tough as nails. I think it takes some biblical wisdom, godly counsel and prayer to navigate those tough situations with real love. But if you’re simply weary from loving and getting nowhere – not loving and getting hurt, mind you – then let me encourage you today to cling to the promise of God’s Word. Love never fails.

Love never fails; but if there are gifts of prophecy, they will be done away with; if there are tongues, they will cease; if there is knowledge, it will be done away with. ~ 1 Corinthians 13:8

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xoxo, Kay
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35 thoughts on “Winter Classics Outfit with a Chambray Shirt and Wool Pants

  1. Nice classic casual outfit. Love the chambray shirt with the pants and blazer.
    I think the black wedge sneakers with the pants would be cute, if style with
    a different shirt or blazer. I think I would not like the flat white sneakers with
    these pants because of the flair. Of course I am not a real big sneaker person,
    more in to booties in winter.
    Loved your BFTD. Sometimes some people are so hard to love, but we have to
    persevere except of cases of abuse like you pointed out. God would never want that.
    God Bless.

    1. Hi Sherry. Thanks for reading and sharing. No I have other ideas for the tweed pants with the black sneakers. It would be quite different. ? Have a great day! ?

      1. I figured you might. You are so classy.
        On your black wedge sneakers, did you get your usual size in them?
        I usually wear a 6 1/2, but if the shoes have pointed toes or run small
        I have to sometimes size up to a 7?

        1. I have my regular size. I will say that when I wear socks with them, depending on the socks, they’re slightly snug. But I probably wear them most often without socks.

  2. Great look on you, Kay! I like chambray/denim. It really makes a classy statement with your camel blazer and your tweed slacks. That’s my kind of an outfit!
    Thanks for BFMD as well. Some people are hard to love, but God is our example. You never know what one kindness will accomplish in someone’s heart.
    Have a wonderful day Kay,

  3. Great post! Thanks for the link to the J. Crew chambray shirts. I ordered the ruffle-front top in leopard and the ruffle-neck classic. Can’t wait to wear them!

  4. I love the wool trousers! My problem is I’m between sizes right now (actively losing weight) so I am hesitant to fill my closet up with things that will end up too big (good problem to have I know!). I am dying to shop though!

    1. Hahaha! Hang in there. You will definitely enjoy shopping for new things later when it counts. Congratulations on losing weight. That’s an accomplishment!

  5. Love your classic outfit today! Thank you for your Blessing today. I am in the middle of loving our grown son and this is a difficult situation when they have joined a cult and are pushing you away. We must just keep loving! Amen!

    1. Oh my. I’m so sorry. Yes, loving can be so hard in those situations. And it can feel like it’s not enough. But this scripture tells us that love supercedes everything else we try. ?

  6. Thanks so much, Kay, for taking another shot at wearing wool pants more casually. I have similar donegal tweed pants in black/ivory and I’ll bet the denim would look good with that as well. Maybe even with my new black Chanel-style blazer. Also have another tweed pant with a light blue fleck that should work. Love the idea of trying not just a denim shirt, but also a denim jacket. I look forward to playing with this look and seeing how I can adapt it. Thanks so very much for giving it some thought and for the inspiration! You work so hard to serve us and we deeply appreciate it.

  7. HI Kay! I finally got onto your blog and I’m in love with your chambray shirt look, I signed up for the sale alert!! I also wanted you to know that this weeks lesson on Joseph is really helping me. Talk to you Wednesday at 10!

  8. I enjoy your . I am fair skinned and have gray hair. I look better in cool colors. Could you suggest an alternative to camel color. I don’t feel good in that color. It looks wonderful on you. Thank you.


  9. Beautiful outfit! The Blessed for my Day really hit home for me! I’m working on trying to continue to love through a tough situation! Thank you for this reminder and example to ‘keep on living’.

  10. I just found your .com
    Site and Instagram site today .. I’m loving your style and styling ideas.. I’m
    Looking for your style quiz .. would like to take it. Thank you so much!

  11. Hi Kay!!! I wanted to let you know that the wool pants and the chambray shirt look just fantastic on you. I’m really happy I found your site, you have so many great things you share with all of us.
    God Bless,