
As much as I want it to be a sunny seventy degrees with blue skies and colorful blooms popping up everywhere, spring isn’t springing quite yet here in Chicago. Don’t worry, it will be here soon, but for now, I’m sharing some outfit ideas for when the weather is hovering around 50 degrees F (10 degrees C for all my international readers!)
For me, highs in the fifties feel quite chilly – a tee and light jacket just isn’t going to cut it. Dressing for spring in this kind of weather takes a little imagination, but my strategy involves keeping most of my winter wardrobe in rotation while swapping out some of my more bulky outerwear for lighter jackets and boots for ballet flats and loafers. Adding in a few warmish weather pieces gives me the satisfaction of spring dressing while still keeping me warm in March and April.
Below I’ve put together seven outfit combinations I use for colder spring dressing. Pretty soon, I’ll be swapping my sweaters for tees and getting rid of my jackets all together! All of these outfits fall under my usual style of casual chic. If you need more business casual looks, swap some of the jeans for trousers.
Casual Chic Outfits For 50 Degree Weather

This is a classic Parisian inspired spring outfit combination I wear all the time. A trench coat is really a core piece in my early spring wardrobe. For colder temperatures, pairing it with a sweater (striped or otherwise) is the way to go. I also start reaching for my light wash jeans more which feel more spring-like compared to darker washes (I still wear those throughout the spring months as well, however.)
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One of my favorite things about spring is jackets! After being confined to a heavy wool coat or big bulky puffer for the last four months, it’s a true joy to wear a light jacket. To get away with a jacket like this, you’ll probably want to layer a bit. Personally, I’d wear a tee under this sweater especially for longer periods outside.
A style note here – I love the contrast of a utility jacket with a softer ballet flat like this. Because my jackets tend to be more structured and masculine, a feminine ballet flat is what I most often reach for in the spring as opposed to a loafer.
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Stripes were made for the spring months. If your outfit is feeling a little too wintery, try swapping your plain button down for a striped one. Here, I’ve paired it with some barrel jeans (I recommend sizing up in these) and ballet flats which makes for a modern outfit combo (you could certainly wear straight leg jeans as well.) I like having a lighter wool coat like this for transitional weather when I don’t necessarily need my heavy wool coat but I’m not quite ready for a trench or lighter jacket. I’ve owned this exact one from Mango for a few years.
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This pairing with a sweater, trousers, and leather jacket is an edgy take on business casual. I think these leopard print flats are the perfect shoe for this look (they are currently on their way to me!), but wear any ballet flat you have to copy this look.
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Here’s a second outfit combination with a trench coat. I love how easily it works with literally anything from leggings to trousers. For this look, we are pairing it with a button front sweater (I’ve linked a few options below!), white or ecru jeans, and sneakers. Even though this look is mostly monochrome, I do love adding a touch of black with the bag and sunglasses to give it a little edge. You could also add a tee under your cardigan here for more warmth, too.
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Here’s a more casual look that would work well for the weekend – a sweatshirt layered under a denim jacket with drawstring pants and ballet flats. If I want to be more comfy, I typically swap my sweater for a sweatshirt – it’s a pretty standard Sunday uniform for me.
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I cannot wait to wear my suede jacket again – mine is from Sézane – and I plan to wear it exactly like this with a button down, light wash jeans, and loafers. This one is pushing the 50 degree weather limit here – I would layer a scoop neck tee under this button down for more warmth.
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Read More:
My Spring Wardrobe Essentials
Stay-At-Home Mom Spring Capsule Wardrobe
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