Casual Shoes-Fashion Over 40

Before Christmas one of my readers, Jeanine, emailed me and asked me what type of casual shoes should she wear when she’s wearing jeans and a nice fleece hoodie or a long sleeve graphic t-shirt.

This is a great question! It would be easy to pop on a pair of athletic shoes but unless I’m in yoga pants (acting like I’m working out :-) ) I don’t wear my athletic shoes with jeans.

If I’m running errands sometimes I wear t-shirts and this time of year, I add a long sleeve t-shirt underneath it. I usually wear my Sperry loafers. I’ve had mine several years but they have a lot of new styles that are super cute!

Casual shoes

I’m wearing my boot cut Ralph Lauren jeans I purchased at TJ Maxx.

I also wear my skinny jeans (they’re actually more like jeggings) and I would pair them with my sperry loafers too. (I took these pictures at dusk, and the lighting is terrible, sorry!)

Casual Wear Shoes
I love these Sperry shoes and I think they would look great with a casual fleece hoodie or sweatshirt.

Casual Wear Shoes

If it’s raining I always pull my rain boots out and if it’s snowing, I have some snow boots.

Casual Wear
That’s what I would wear but what about you? Do you have any ideas for Jeanine? 

Beauty For the Heart~~One of my favorite verses I read this morning, 2 Corinthians 12:9, But he said to me, “My grace is sufficient for you, for my power is made perfect in weakness.” Therefore I will boast all the more gladly about my weaknesses, so that Christ’s power may rest on me.

Have a Blessed day!

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  1. says

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  2. Brooke says

    I realize this is an older entry, but could you tell me the brand of the skinny jeans/jeggings? Thank you!

  3. Paula Dutton says

    Since we are expecting snow again here in NW Arkansas (that will probably kill our fruit blossoms) I thought I would tell you what has kept my feet warm and looked better than my usual ‘sneakers with jeans.’ I have some black Uggs sneakers that look like Converse. They are fur lined and comfortable! I saw some at Dillards, but I think I got mine at my fav shoe outlet–Wilkinson’s in Conway, AR last year. If you are ever in Little Rock you should take the short drive and check this place out :)

  4. says

    Hey Jane,
    Truthfully, I don’t wear socks with my Sperrys. They’re boat shoes, I think they look best without socks. Also, I don’t think I’d wear socks with Toms. With flats, I wear thin trouser socks. If it’s really cold, this I stick with boots!

  5. Anne Marie says

    Cyndi, it never occurred to me to wear something other than tennis shoes on my jeans/sweatshirt/hoodie/tee-shirt days! I am going to dig out my Sperrys from a couple of years ago which I’ve hardly worn, and today I invested in a pair of the Sperry leopard loafer flats. I love them and can’t wait to wear them! Like some of the other comments, I feel frumpy when I wear my athletic shoes with jeans, but you’ve reminded me that I don’t have to do that! Thanks!

  6. Lori says

    Stumbled across your site after searching, ‘Women over 40’, and I’m so glad I did. What a useful, uplifting, speaking Words of Life site you have. :)
    Enjoyed reading a couple of your articles, but after seeing you sporting a U.K. tee above…I’ve bookmarked your site to come back to often. Go Cats! 😉

  7. Amy says

    My burlap Toms are my favorite new go to shoes. They are so versatile and so comfy. Really really cute too.

    Love all of your great posts, my friend.

  8. Karen In NC says

    I second the socks question. I never know but it is too cold not to wear something. Thanks for the great posts!

  9. says

    Clogs are a nice go-to because you can wear heavier socks with them. I love Clarks. Question for you, Cyndi – what kind of socks do you pair with the Sperry loafers when it’s really cold? I have some cute flats, but they look sorta creepy with socks. And does anybody ever wear any type of socks with Toms? They have a cute look, especially the wedges….but, when it’s really cold, there’s that whole sock issue….

  10. judith hall says

    I love Clarks brand shoes. They make many styles of structured or unstructured shoes in slip-on, ballet flat styles and something they refer to as a clog, but the heel is only about 1 in. tall. They also make clogs with up to a 2.5 in. heel. I think they work with all kinds of jeans and top combinations.
    My opinion is that jeans with athletic shoes outside of the home goes away in a woman’s late mid to late thirties.

  11. Kim says

    I live in Michigan which = cold. I wear my UGGS pretty much exclusively with jeans and hoodies. Also, love my White Mountain and BCBG riding boots. I think the only thing I like about the cold seasons coming is getting to wear my boots endlessly!!

  12. Michelle says

    Yes!! I wear these too! I live in Michigan and it gets cold so I need socks!! These look a little more dressed up and are really comfortable!!

  13. Fran says

    Cool Shoes found a pair on ebay 21.00 brand new.. can’t wait to get them thank you so much Cyndi YOU ROCK.. God truly guides you.. That is part of my nightly prayer for him to bless us to bless other, teach us to teach others lead us to guide others.. your truly blessed!!!

  14. teresa says

    I have those same Sperry’s and wondered why all the young people I meet always comment on them…I didn’t know they were fashionable! I ususally wear boots with jeans in the winter and around the house I’m always in my acorn slippers. I’m with Jeanine, it’s just too cold to wear anything other than heavy socks. I will do ballet flats in good weather although i don’t find them particularly supportive.
    BTY, I LOVE the “jeggings”! May I ask when you bought them. They are super flattering and i think I might be able to wear them without looking like a drumstick.
    Thanks for yet another great post.

  15. Casey says

    I love my Sperry’s! Wear them all the time. It might be time to buy a new pair. I’ve had these for about 6 or 7 years. I also wear short suede boots with t-shirts and jeans. I always have a hard time finding the “right” shoes for winter to wear with casual clothes, guess that’s why the Sperry’s are worn out! LOL

  16. says

    Hi Cyndi~

    Winter time its boots for me or a pair of clogs. I don’t usually wear flats, although they do look cute, I prefer a 2 inch heal. My clogs are “Born” from TJ Maxx and they are SOOO comfortable…like slippers. AT home around the house I’m in slippers… :) thx for the great ideas!

  17. Tangi says

    HAHAHA! I learn something new everyday. I honestly have never considered wearing anything other than sneakers with a t-shirt/hoodie and jeans. But the Sperry shoes are super cute. I’m so not fashion savvy, but I’m trying! Thanks for this post.

  18. says

    You have a lot of great suggestions. I like to wear my Toms with my skinny jeans and casual athletic tops/ hoodies!!

    Blessings from Texas!!

  19. says

    Hi Cyndi!

    Love your ideas. :)

    I usally wear boots or ballet flats with my jeans. I wear a lot of skinny jeans, and I wear ankle boots with a heel or flats with those. When I wear my boot cut jeans, I’ll usually throw on my cowboy boots. I have a pair of dark wash, straight leg True Religion brand jeans that I love, and I can wear boots with the jeans tucked in or ankle boots with a heel with those.

    Thanks for the post and the ideas.

    Have a great day!

  20. Jeanine says

    Whoop Cyndi! You nailed it! I am so grateful for your suggestion of Sperrys (never considered those) and all these great comments. I do have a pair of ballet flats but truthfully, this time of year my feet get cold and I have to resist the urge to put socks on with them, and I mean I want the over the ankle socks, not those no-show kind. Ugh! I know! I think Sperrys are just what I need and I will be checking out these other suggestions. Many thanks!

  21. says

    I have two pairs of go-to shoes right now with jeans. One is a pair of leopard Sperry shoes. They are so cute! I also have a pair of Coach shoes that are styled kind of like tennies but much cuter. I get compliments on both of them all the time. I’d like to add more ballet flats but find that so many of them are really uncomfortable.

  22. says

    I have some Sperry’s but I also do ballet flats too. I find the timing of this hilarious because I’m wearing a t-shirt and jeans today and haven’t done that in weeks!

  23. says

    Love it, Cyndi! I love jeans, a nice shirt and some boots or ballet flats. But this time of year for just sitting home with the kids or running to the grocery store, I tend to do jeans, a hoodie and sneakers. As comfy as it may be, I have to admit it makes me feel so frumpy. Definitely going to try to find me something like this! :)


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