Hey y’all! I know we all have skirts in our closet that we would like to be more multi-purpose than just wearing on a few of the 52 Sundays a year, which is why I’m so thrilled to be making this series. As a bonus, this outfit also shows one of the dozens of ways to pair a t-shirt with a skirt without looking sloppy. Where would I wear this outfit? To run errands, to Friday night fellowship, for Sunday afternoon chillaxing, and to hang at home with the possibility of seeing people, like I’m doing today. 🙂 
Today’s chosen skirt for our “Dressing Down” series is one of the first skirts I ever bought after deciding to dress more deliberately. I’ve mostly worn it to church, but today I paired it with a t-shirt for a casual look. I didn’t intend to promote the new Fresh Apparel t-shirts today… but actually, that’s an announcement I haven’t made on the blog yet! FreshApparel.us is open for business! Right now there are only a few t-shirts for sale, but eventually that will be the marketplace for the Errand #17 skirt! If you’re hoping to get a t-shirt like this one, you better hurry because we’re starting to sell out of sizes! Free shipping right now, too. 

To wear a t-shirt with an elastic-waist skirt, here are a few tips:

1) Choose a skirt that doesn’t have excessive gathers at the waist. Opt for something that has a slim bunching instead of bulky fullness. 
2) Choose a t-shirt that isn’t too long or too loose. To pull off this look, you’ll need a t-shirt that fits in the shoulders, falls easily on your hips, and doesn’t have a super tight neck binding. Don’t pull the shirt down all the way if you’re short like me and the hem hits below your natural hips. 
3) Choose footwear that marries the two looks. I chose black leather flip flops that I would wear with the t-shirt and a denim skirt, and with the skirt and a white ruffled shirt after church. Tennis shoes would not go with this look because I wouldn’t have worn them with that skirt, nor would heels work with this because I wouldn’t wear them with that t-shirt. 

// outfit details //
T-shirt : Fresh Apparel Denim Co (Woohoo!)
Skirt: Apt.9 : Kohl’s
Flip Flops: American Eagle : Sears
Earrings : Droplette Jewelry
Do you have a piece of clothing that’s stuck with you for what seems like forever? How do you make it work for different occasions? I hope y’all  have a great day! 

53 thoughts on “Dressing Down | 3 Tips For Pairing T-Shirts With Skirts”

    1. I noticed that, too. 🙂 It looks nice, Olivia!

      I really like the idea of dressing normally dressy skirts down, and I really think this post will be a help to me, and many other ladies, also. 🙂

  1. Would you have put flats with your outfit? I don't like putting sneakers with skirts like that either, but for winter time coming in its either the former, latter, or dress boots.~ Kelly M.

    1. I probably wouldn't wear a dressy pair of flats with this, but maaaaybe some black Keds or something. Honestly, I don't usually wear this skirt casually in the winter because it's length is awkward with closed shoes. :p

  2. Hmm thought your hair looked different 😉 Hey, I can get some Fresh Apparel shirts for my brothers HAHA I had thought it was a girl's brand. Cool 🙂 I love your outfit! And I'm liking the site!


  3. Hi Olivia!
    I like your hair! And those tips for dressing down a skirt are very good!
    Would you be interested in doing an interview on my blog? I think that would be a lot of fun. 😉

  4. I love the look! I love wearing skirts and t shirts together,but I often have add leggings or pants underneath too,living in Alaska I hv to be a bit more creative! Thankyou for your encouraging blog….it's great there are young ladies setting Godly examples in dress…I completely agree we don't have to look frumpy to be modest and we can still dress attractively without dressing to attract 😉

  5. I thought so – it's really cute.
    This is very impressive. What a cute outfit. I never would have thought to wear a t-shirt with that skirt. Beautiful!

  6. I saw you pin a red hair color thing the other day, panicked and hoped you wouldn't go for the dark reds. 🙂 It looks good!
    Great tips for casual skirt wearing! I've been hoping to get more casual skirts into my wardrobe. I have NONE except for maxis right now. Expecting a black mid-calf length skirt from thredUP tomorrow! So excited!
    Thanks for the great post!

  7. lol I was going to say that the skirt / the lighting must be bringing out reddish tints in your hair! 😉 I love it! I'm not a big fan of colored hair generally, but this is so well done and natural looking! =D

  8. My favorite purple floral skirt… I've owned it for about four years, and wear it all the time :). Paired with a purple tee shirt, it's dressy enough for church and simple enough for a simple outing, though since the material is a bit more delicate and I'm kind of rough on clothes :P, I don't wear it at home much :).

    Your hair looks wonderful! I just wondered, though, did coloring your hair affect you "season", or was it close enough to your original color? I just found you blog through a friend's blog, then KBR magazine, then another friend shared it, and I've been having fun reading past posts the last couple weeks, I was just reading your "appearance goals" post where you talk about finding your season, and just wondered if you'd have to switch out your clothes every time you did it :).

    Blessings to you!


    16 Year old blogger of "Forget Not His Benefits", a blog on Thankfulness, Family, and Following God

  9. Your hair looks amazing! Seriously, you ROCK hair with a tint of red in it! You look so beautiful in these pictures. Also, love the tips! I have a denim skirt that I've been wearing SO much for a couple years, and to dress it up I usually wear a cardigan or button-up/high heels or flats and casual flip flops/t-shirt with it to dress it down.

  10. I've been meanimg to ask you why you wear make-up. I don't want to seem mean but isn't it vanity? Shouldn't we be happy with the face God gave us? The only time its brought up in bible its with whores that paint their faces.

    1. Dear Anonymous,
      I think that the decision to wear or not to wear makeup should not be confused with Biblical instructions for "painting the face"…because there are none that specifically say, "You must wear this amount of makeup and no more," or else, "You absolutely MUST not wear makeup under any circumstances." It's a personal decision between you, the Lord, and sometimes your parents, if you are still living in their house.

      Do you know why whores paint their faces? To draw attention to themselves and to the fact that they're prostitutes. The way they paint their faces is not that different from the way some girls use mascara and blush and other products today. BUT, we have a choice on how much makeup we use. I've seen some girls who have so much mascara on, it seems to draw attention only to their eyelashes, and not to the other beautiful features that God has given them. I am not at all opposed to wearing makeup, but I have restrictions on how much I will put on. My reason for wearing mascara is not to draw attention to myself, but it DOES make me look nicer (my cheeks rosier, without the help of blush, my eyes brighter, etc.) when I wear it. However, I do not feel that it is necessary for my character, because my character is not based on my outward appearances.

      In an attempt to help others to understand what I mean, let me give an example. In the same way that makeup can enhance our beauty (with the right amount used), so can clothes. The reason I like to wear cute skirts to church is because I know it looks nice, and I personally feel that it is honoring to the Lord when I dress nicely to worship Him on Sunday with other believers. For me, it is the same way with mascara. I wear a little of it now and then, because I know it looks nice. Again, though, my character is not based on my outward appearances, so I am not depending on mascara to make other people like or notice me.

      I agree with you that we should be happy with the face God gave us. But is it vain to dress nicely? Is it vain to wear makeup? It depends on what your motives are. I know it certainly CAN be vain…but it doesn't have to be. Since nowhere in the Bible does it say that we should or should not wear makeup, I believe it is between you and God. I certainly am not against NOT wearing makeup, but I also feel that if you use the right amount of makeup, you can enhance your natural beauty instead of disguising it.

      I know I am treading on a very touchy subject, and I hope that I have not embarrassed anyone or said things that I shouldn't have. It is very hard to put in words what I am feeling, and I wish I could speak with you face-to-face. Thank you so much for putting this subject forward, because it has made me think harder on what my motives are for wearing makeup.

      In Christ,
      Anonymous # 2

    2. You should read more of this blog – Olivia has posted about make up and how she uses it in earlier posts. Plus this blog is excellent so you should read more of it anyway 😀

      Also, whores? Really? I think the way women use make up has come a long way since then…you can definitely make modest choices in how you use make up.

      ~Esther of Oz

    3. Haha, I love the community of readers Fresh Modesty has! I wasn't able to respond to anonymous right away because of computer issues, but y'all have done a great job!
      My thinking behind wearing make-up is that it is a way to cultivate the beauty the Lord has given us. I have no issues whatsoever going without make-up, but I feel I am a better representation of my own self when I do wear it. In one of my make-up videos, I explained that I see make-up as a "varnish" that just brings out the natural beauty of the "wood".
      And, if we look through the Bible for instances of God's people making things more beautiful, it becomes very clear that God highly values beauty and cultivating it. I'm out of time to comment any further, but there's a few thoughts to answer your question. 🙂

    4. thanks for explaining why.:) I"m not trying to judge just wonder why. some people wear it i away that seems really vain but you dont.:)

    5. A Verse that i thought might be useful for you all:
      "Whose adorning let it not be that outward adorning of plaiting the hair, and of wearing of gold, or of putting on of apparel; ~1 Peter 3:3

      And another interesting text i found:
      Moreover the Lord saith, Because the daughters of Zion are haughty, and walk with stretched forth necks and wanton eyes, walking and mincing as they go, and making a tinkling with their feet: therefore the Lord will smite with a scab the crown of the head of he daughters of Zion, and the Lord will discover their secret parts. In that day the Lord will take away the bravery of their tinkling ornaments about their feet, and their cauls, and their round tires like the moon, The chains, and the bracelets, and the mufflers, The bonnets, and the ornaments of the legs, and the headbands,and the tablets, and the earings, The rings, and nose jewels, The changeable suits of apparel, and the mantles, and the wimples, and he crisping pins, The glasses, and the fine linen, and the hoods, and the veils. And it shall come to pass, that instead of sweet smell there shall be stink; and instead of a girdle a rent; and instead of well set hair baldness; and instead of a stomacher a girding of sackcloth; and burning instead of beauty. ~Isaiah 3:16-24

  11. I love the shirts! I'm so excited that everything is working out for your new business!

    I like how you dressed down the skirt with a tshirt. . .but I seem to have a closet full of those nasty, shapeless, unisex shirts that look like a potato sack with a skirt. 🙂

  12. Hi!

    Love this series! I have so many dressy skirts and now I can do something with them!

    Also, I asked before about signing up for the newsletter. I went through the process of signing up a few weeks, but still have not received anything, so I'm just letting you know. It's probably my computer that got something mixed up. Did you send one out yet? Thanks!

  13. Hi Olivia! I can't wait to get my Fresh Apparel t-shirt. 🙂 I look forward to getting your Errand skirt as soon as it's available! You are a wonderful Christian role model and I want you to know that. I am 36 and it's because of you and Caroline (over at The Modest Mom) that I have learned more about modesty than I ever knew before, even though I'm a missionary kid and grew up in the church (kinda sad….). Keep us posted on your wonderful new business! And as an encouragement to you in view of the anonymous comment above me about makeup, I think you do a wonderful job of highlighting who you are in your physical appearance; in other words, I can tell that you do not dress to draw attention to your physical appearance, even through your makeup (which I personally can hardly see because it's so natural). Using makeup could be a point of vanity, and probably is, for many women, but that is our individual accountability to the Lord as only He knows the heart (Jer 17:10; Matt 12:35). As your recent post pointed out (yesterday I think), it's about our individual accountability to the Lord to be modest. I pray for you as you continue on the path God has called you to here online as an encouragement and "sharpening stone" for we who are your readers. 🙂 ~ christine

  14. Love the outfit Oliva, its really beautiful! I love your new hair, So pretty! A great colour on you! What do you think about wearing sleeveless tops? Because they're just your shoulders..but am wondering.

  15. I really love Fresh Modesty and Olivia, but i have to say i miss Olivia's blond hair… it was so beautiful!! i dont know why she dyed it 🙁 This hair colour is nice too, but her natural hair colour is even prettier, i just dont see the point in dyeing it… Just my opinion though! 🙂

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