10 Casual Winter-to-Spring Outfit Ideas

by - February 11, 2023

I don't know about where you live, but the weather here in the South has been all over the place the last few weeks. While it has been aggravating going from cold to hot and back again (in more ways than one), it does mean this edition of Real Outfit Roundup has some good examples of transition outfits.

Moving from one season to the next can make getting dressed in the morning difficult. Lucky for you, our unpredictable southern weather has made me pretty good at transitional dressing. I mean, sometimes we transition through all four seasons in one week!

Sizing note: I'm 5'2" and weigh about 140 lbs. I typically wear size 6 or small/medium in clothes and size 7 in shoes.

This is the only cold-weather outfit in this roundup. This was a really cold day for us, but I didn't want to wear something that felt like it just screamed winter. So I lightened up this fair isle sweater with white jeans. It's a really easy way to add a taste of spring to an outfit.

My sweater is still available in limited sizes and is on sale. I am wearing a petite medium in this. It's a good bit thicker than what I usually prefer in sweaters, and the neck is fairly high. I like the length of the petite, both in the body and sleeves. However, the shoulders are almost too snug.

My jeans are several years old. They're the a.n.a. brand at JCPenney. I really like the fit of these, but this exact pair is no longer available.

I wore boots this day because it was so cold, but I don't love how dark they are in comparison to my jeans. I don't regret my decision because, again, it was cold, but I think a more neutral color would have worked better.

Collared sweaters are a trend I didn't think I would like, but I decided to try it anyway, and I'm glad I did. I feel like this sweater fits very nicely into my closet. I like how it makes a pair of jeans feel elevated, especially with these loafers, but I also think this will work nicely with skirts and dress pants. It's a thin sweater so it will work through most of the Spring. I really like the fitted, ribbed knit, and the v-neck collar is a nice detail I didn't appreciate until I put it on. It also comes in a pretty blue and black.

My jeans are the mid-rise power slim straight from Old Navy. I really like this wash (it's called Willow). They feel very middle-of-the-road casual to me. These are probably my favorite straight-leg jeans that I own. However, they're about an inch and a half too long, hence the slight bunching at my ankle. I can't go down a size because of my hips, and the short inseam is too short for me (go figure).  I haven't figured out how to cuff them yet. They really do fit perfect everywhere else, though, so I'm going to keep wearing them.

Everything in this outfit is old, so sadly I don't have anything to link to. These are my favorite pair of jeans, and they're starting to wear out after years of near-constant wear. I've been looking for a replacement and haven't found one that I like. My t-shirt has a little astronaut hanging from the moon and is no longer available. My shoes are a year or two old. I got them on final sale for $10. They're amazingly comfortable but a bit ridiculous because the pink is so bright. I rarely wear them, but decided to bust them out since this style is in right now.

I have had my skirt in my closet for over a year just waiting for the right opportunity to wear it. Then I decided that was never going to happen, so I made my own opportunity and didn't regret it one bit. I was initially worried that I would feel overdressed with the skirt, so I intentionally chose casual pieces. I think the faux leather white sneakers were the key piece in dressing it all down, though. The skirt is tulle with shimmery stars. It's fully lined with an elastic waistband. I chose a bodysuit because they don't bunch when tucked in, and I wanted something a little darker to finish the top off. Overall, I love the way this turned out...and so did my students!

Shirt / Jeans / Boots (out of stock)

Have you tried Old Navy's poet blouses yet? They are arguably my favorite style of shirt these days. I love how flowy they are! This one is so pretty in person, too. It's perfect for spring but can easily be layered under a light jacket for colder days.

My jeans are the mid-rise kicker bootcut from Old Navy. I really like this style, and I like that the bootcut is narrower than other styles. It's more proportional to my height. This is the darker wash, but I'm ordering myself a mid-wash as well for more casual outfits.

These boots are one of my most favorite pairs. They are several years old and no longer available, but they are a great neutral color, the perfect heel height, and go with just about anything. I'm going to be sad when they eventually wear out, especially since I can't find anything even remotely close to replace them with.

When I came across this dress in Target, I couldn't resist it. Then I couldn't wait to wear it, even though the weather wasn't exactly right for it...so I improvised! Layers were needed, so I started with a light purple t-shirt underneath the dress. It helped to pull out some of the lighter colors in the dress's pattern, but the outfit still felt incomplete, so I reached for my tried-and-true dress topper - my denim vest. Because it was still on the cool side, I finished the look with my navy blue flats.

Would you believe I bought the items separately with no real thought that they would go perfectly together? Me neither, but it's true! I ordered the t-shirt because I wanted something understated for Valentine's Day, then I found the skirt on a random Target trip. At first glance, this looks like your classic polka dot pattern, but on closer inspection it's really a heart print. So it only made sense to pair them together!

In case you missed the memo so far, Old Navy has got some really cute spring tops right now. I almost didn't order this top because it's a babydoll style, and those tend to feel a bit too young for me, but in the end I'm glad I gave it a shot. It's really flattering on, and I love the puff sleeves. This is the birch leaf color. It's not quite so dark in person.

My jeans are the high-waisted wow slim straight from Old Navy. I find that these are a better length for me than the mid-rise power slim straight. They hit right at my ankle, so it's more flattering. However, this pair, which I got at the same time as the other pair, have now gotten a bunch of little pulls in them. I don't know how, either, because I'm wearing them in the same capacity as the other. It's, thankfully, only noticeable up close, but it is aggravating.

I'm not fully satisfied with this outfit. I think it's the shoes, which I almost didn't wear, but in the end I chose comfort over a better color match.

This is another of Old Navy's poet blouses. It is a much thicker material than the one shown earlier in the post. Because of that, it fits much more structured, so not as flowy, making it more difficult to do a front-tuck with as you see in this picture. In fact, I wore it fully tucked all day at school because it was more flattering with the cut of these pants.

Speaking of the pants, these are the curvy high-waisted OG straight cut in a beige color from Old Navy. I really love the color, but I'm not sold on the cut for me. It started out great, but as the day wore on they got looser and looser, resulting in the almost bagginess you see here. I'm hoping a run through the washing machine will help with that. I guess I'm not as curvy as I thought.

This was kind of a weird weather day for us, and I didn't really know how to dress. In the end, I did regret the white shirt but only because it rained, and I was not expecting rain! I actually love this shirt so much that I also own the short-sleeved version of it.

These are the same mid-rise power slim straight jeans I talked about earlier in this post. My jacket is from a StitchFix box. It's made by Liverpool Los Angeles, but this style is no longer available. You can check out what else they have here.

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