
Looking for ways how to wear a blazer with high-waisted trousers? Then these stylish outfits are for you.
To wear a blazer with roomy high-waisted trousers is a practical approach for women who likes to stay comfortable yet chic.
It´s amazing how much blazers have evolved from being mainly a corporate outfit necessity to a creative wardrobe staple. It used to be only „blazer and pencil skirt“ or „blazer and suit pants“, but now you can include a long list of fun combinations – blazer and dresses, blazer and shorts, blazer and skinny pants, and the list goes on.
I love how a simple outfit can quickly look stylish by adding a blazer. One of my go-to everyday style this season is throwing a blazer over a comfy combination of a t-shirt and high-waisted trousers. I wear this look all the time whether it´s to pick up my son from daycare or to stroll around the city for a day of family time.
Teaming a white t-shirt with a soft high-waisted trouser is my favorite style at the moment because it makes chasing my two-year-old a lot easier. My movement isn´t constricted as it would with a tight skinny jeans. But even if comfort is high on my list right now, I don´t want to sacrifice style. So I add a nice blazer. By adding a blazer over a simple outfit I quickly feel and look stylish while staying comfortable.
If wearing a blazer with high-waisted trousers is something you would like to explore, then read on for some beautiful inspirations.
Table of Contents
1. Wear a Blazer with High-Waisted Jeans and Ankle Boots
In my article how to wear jeans, I alloted a good portion of it discussing ways to wear boyfriend jeans. As you can guess, that´s because boyfriend jeans are included in my go-to comfy trousers since I became a mom.
Worn with a cool t-shirt and some pointed-toe ankle boots, and then pulled together with a gorgeous blazer, you´ll have a look that´s nothing sort of mom-look but a fabulous street look at that.
The key to looking great in this outfit however is having the right boyfriend jeans that flatter your figure and then finding the perfect blazer to go with your jeans. Whether you opt for a high-waist or a mid-rise jean, you want to make sure that the jeans flatter your rear and does not cut your vertical line.
To be honest, it took me so long to find the perfect boyfriend jeans for my petite figure. But once I found it, I had a lot of fun wearing it with blazers.
2. Wear a Black Blazer and Yellow High-Waisted Trousers

Another approach to going comfy yet stylish is mixing a bright colored high-waisted trousers with a black blazer. Let everything in your outfit be black — from your t-shirt, to your blazer, and to your shoes. This will make your bright trousers standout.
Remember too that although you´re choosing a black blazer for this look, it doesn´t have to be entirely muted. If you want to add personality, edgy details or striking buttons, you can design your own blazer online. There are online boutiques which let you do this with just a few clicks of the mouse. Better yet, why not pay your favorite tailor a visit and ask her to help you design your blazer?
3. Wear a blazer with bright high-waisted flared trousers to Colorblock
I once had a reader asked me “how to colorblock a royal blue blazer“. During that time, colorblocking was a huge trend. Although no longer a hot trend, colorblocking still lingers. For me though, I found investing on a white blazer a practical move. I can colorblock it with anything.
If you have a bright high-waisted trousers, choose a complementary color for your top and then throw over a white blazer. You will never go wrong with it.
4. Create a tonal look with a blazer and high-waisted trousers
I think we can all agree that a plaid blazer is a woman´s wardrobe staple. I have three plaid blazers in my wardrobe.
Although patterned, it goes well with any monochromatic outfit that you´d like to create. Choose a high-waisted trouser in a solid color that matches the shade of your plaid blazer. Add accessories that blends with your blazer and trousers for an ecclectic monochromatic look.
5. How to Wear a blazer and high-waisted trousers with sneakers
It´s empowering to think that women now have the option to opt for casual business outfits. If you´re your own boss, or if you work in a creative field, or if you have a versatile work environment, wearing a blazer with high-waisted trousers and sneakers is a fabulous outfit to don.
Stick with tailored carrot leg and on-tend paperbag waist for your trousers. And of course, keep it safe with muted tops and white sneakers.
A casual yet chic work outfit is definitely something that I wear everyday. This look is one of my favorites.
Whenever you feel unsure how to wear a blazer with high-waisted trousers so that you stay comfortable, team it with some roomy high-waisted trousers. You´re not only comfy and chic, you´re also on trend.