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This “Need help? Here’s how to ____!” is a 3 part series where I style someone else on my blog! Over Christmas, my wonderful cousin, Maddie, came to visit, and not too long after she got here, we got hit with a big old blizzard. That’s the midwest for you! Snowed in with no place to go, I threw out the idea of styling her in some outfits. Thankfully, she loved this idea because though she loves fashion, she finds it pretty challenging and it doesn’t come easily to her. Her words, not mine! I asked her what her 3 biggest fashion questions were at the moment and this was her first one- how to wear a chambray shirt.
She picked a chambray/denim shirt up because I recommend them a lot (aww), but she needed more guidance on how to actually style it.
She said, “I know that plain is sometimes best but I don’t know what to do with it. I like to look classy and simple in my day to day life. Sometimes I like a loud print too though.”
With her style goals in mind, I picked out 5 different outfit combos using things in my wardrobe. I’m no stylist, but it was really fun to do! I’m pretty pregnant and can only fit into like, 2 things at the moment haha. So this was a great way to use my clothes to dress someone else for a change. It’s interesting as well to see what things look like on different people. Let’s get into the outfit ideas, shall we?
How to Wear a Chambray Shirt
1. chambray shirt + white tee + black jeans + brown boots
I wanted to pick out a range of styles using this chambray shirt to show Maddie (and my readers) how versatile this piece is! I’d say this first look falls under casual cute. The brown boots with a slight heel not only break up the colors and add a great neutral pop, but it takes the look from super casual to a little dressier.
Double denim is a thing, but if trying to figure out what type of blue jeans look good with your denim shirt sounds too stressful, just forget it all and go with black! It will always look good together.
2. chambray shirt + blazer + animal print skirt + heels
Maddie is a school therapist so though she works in a professional educational setting, her job attire is pretty casual and she would never wear a skirt or heels to work! But still, I knew some of my readers out there have jobs that require a more elevated look and I wanted to show how you can look professional yet stylish yet not too fussy with this chambray shirt.
A chambray shirt dresses down any look, while a blazer, heels, and structured bag add the classy. An animal print skirt is for fun and style!
3. chambray shirt + striped dress + white sneakers
For casual days and weekends, this combo comes in handy. A 3 piece look (4 if you count the bag) is all that’s needed to achieve casual-cool style. Add a baseball hat for extra chill vibes. This look would be great for spring!
Related:
6 Outfit Ideas For When You Don’t Know What to Wear
How to Look Stylish With Hardly Any Extra Effort
4. chambray shirt + jeans + loafers slides
Mixing denim can be tricky. I like to go with the “opposites” route. If your chambray shirt is lighter then go for darker bottoms and vice versa. When in doubt, just pair your chambray shirt with black jeans. But when done right, a denim shirt with denim jeans is cute, cool, and casual. It makes a great base for any extra layering or prints too.
5. chambray shirt + jeans + blazer + loafers slides
Take the look from above and just throw a blazer on it! Seriously one of my favorite ways to elevate any look. You look chic without trying too hard.
A chambray shirt can be a top, a jacket, a layering piece, or an item used for interest just tied around your waist. It can be worn in all seasons and to all places whether it’s work or the grocery store. You can tell I’m a big fan!
So what do you think of these looks? #5 was my favorite and it happened to be Maddie’s as well.
All in all, we had fun and most importantly, Maddie ended this styling sesh feeling like she actually had some ideas on how to wear a chambray shirt. She never thought about pairing a chambray shirt with black jeans and that was the first way she was going to wear it now!
What do you think her next fashion problem will be? Stay tuned to find out! In the meantime, keep reading- How to Build a Wardrobe from Scratch


Thank you Carolyn-
Hope you are feeling well with your pregnancy.
I’m having so much fun with your ideas.
I’m 70 and have a bit of extra around my middle, plus I’m short waited. So tucking in my shirts is out. I especially love the Parisian style info. I even had a French man tell me I looked great/European/French! All I did was wear my trench coat with jeans!!!
Anyway love reading your articles. And thanks again.
Pat
Hi, Pat! I’m really happy to hear you’re loving the ideas so far! Also, what a huge compliment from the French man! Keep rocking that chic style.
I’m looking forward to more in this series. Thanks so much for generously sharing your styling tips.
So happy to hear this! I’m excited to share more. 🙂
I never know what to do with a chambray shirt either, so I was excited to read this. But I thought they looked sloppy, and I didn’t find one I want to wear. And I keep thinking, these are slim models. A person a little overweight like me would look even sloppier. I want to look more put together.
Hey, Claire. We showcased a variety of styles here, from casual to put-together (Outfit #2). A chambray shirt is a casual item in itself, which is why you may think it doesn’t look as polished as you would like.