Curious on how to style trousers now that they are seemingly everywhere? From tailored menswear-inspired silhouettes to relaxed wide-leg styles, they’ve officially earned a permanent place in my wardrobe for the last several years. If you’re wondering how to style trousers in 2026, this post breaks down outfit ideas for every season, occasion and silhouette, using pieces I actually own and wear.
Truth be told, up until a couple years ago I was a jeans girl through and through. But nowadays I really love wearing trousers – particularly high-waisted trousers, straight leg trousers and wide leg trousers. But I also had to learn how to style trousers so that they fit my personal style aesthetic.
Today’s post is fully updated and designed to help you learn how to style trousers for every season. You’ll get outfit inspiration and you can shop my favorite styles that I own.
How to Style Trousers
How to Style Trousers With Ballet Flats
When it comes to how to style trousers, I’m rather partial to this look.
The above pair of J.Crew Trousers have been my all-time favorite and most worn for several years but unfortunately the brand discontinued them!
That being said, this is an easy outfit to replicate. I think a good crepe trousers, when styled with a ballet flat, is an outfit that is great for meetings or work days when you have to be on your feet a lot.
To add some visual interest, I added a sweater with button details along the sleeve and a chic belt.
Related: Ballet Flats Outfit Ideas
How to Style Trousers With Sneakers
Can trousers be styled casually? 100%!
The most common way I wear trousers – particularly wide leg trousers – is with a sneaker. It is an effortlessly chic combination and one that is particularly great for travel days when you’re exploring a lot via foot.
You can shop my favorite shoes, inclusive of my collection of sneakers HERE.
How to Style Trousers in Summer
Linen trousers are the ideal way to wear trousers in summer! Linen head to toe is a go-to look for me all summer long over swimsuits. So easy, so comfortable and yet put together looking.
Reformation always has good linen pieces.
Alternatively, I love the fabric and fit of these & Other Stories trousers I’m wearing above. I sized up to an 8 as the brand usually runs small in its bottoms and tops I find. I have owned this pair for years in the cream and bought the black as well – they are so great.
For summer styling, I paired them with a knit tank and a lightweight silk sweater over my shoulders.
I usually find the best knit tanks at Reformation and Sezane.
How to Style Trousers in Fall
This is another example of my monochromatic looks with a favorite pair of trousers by M.M.LaFleur (size 6). They don’t wrinkle which makes them excellent for travel in particular but the wool twill fabric is truly gorgeous.
You can use code WIT&WHIMSY20 for 20% off your first order with the brand.
How to Style Trousers for Spring
Perfect for transitional weather, I’ll pair a short sleeve sweater with a pair of trousers. J.Crew makes some of my favorites.
The above pair is one of my very favorite pairs of trousers- the Aritzia Effortless Pant. It’s been such a success for their brand that they now have it in various fits, lengths and fabrics. I always size up in this brand and wear an 8 in the regular length. They do not wrinkle which makes them so good for travel and long days.
How to Style Trousers in Winter
As you head into Winter weather, a classic car coat or a great wrap coat makes the perfect topper for trousers.
This look is also a good example of how to wear trousers with sneakers for casual & travel looks.
Just ensure it is the right length so your proportions are aligned.
How to Style Trousers For a Night Out
I love a pair of black faux leather trousers for evenings out in winter and fall. I like to pair my dressy trouser outfits with a tried and true classic black pump usually and often a silk camisole and a little jacket.
In Winter I would add a favorite oversized wrap coat.
How to Style Plaid Trousers
Like a little pattern play? Consider a black and white check like above. This plaid pair is by French brand Sezane. They have a lot of great trouser styles. I typically get them hemmed for my 5’5″ frame.
Related: The Best Sezane Essentials
How to Style Silk Trousers
Silk or satin trousers are the easiest way to be elevated yet comfortable. They also happen to be one of the trouser trends we’re continuing to see everywhere in 2026.
I always pack a pair in my suitcase for evenings out or travel days. Above I’m wearing the Reformation Olina pant in a M. They come in loads of colors. (Seen paired with this sweater in a size L).
Satin pants are a dream to travel in and my favorite way to style them is with a cozy knit. Comfortable and yet slightly dressed up. For evenings out once I arrive at a destination, I reach for heels, while ballet flats or sneakers work perfectly for days spent exploring.
I also own this pair by Vince in two colors (size M).
I love the Varley pants in particular as well (I have them in a size S).
The LaLigne Colby pant (seen above in size M) and Jenni Kayne Demi Pant are also great if you like more of a wide leg when you style trousers.
For a fun pattern, try these Toteme patterned silk pants I *adore*. Like pajamas but still elevated and beautiful. Wearing size 36. Seen styled with this sweater (size S).
Toteme makes a lot of trousers in beautiful fabrics and with excellent tailoring.
Trouser Outfit Ideas
Trousers with an Oversized Blazer + Sneakers
I love the juxtaposition of a pair of trousers with a blazer and sneakers. I like the blazer to be a bit oversized and often pair it with a striped tee or a great plain tee. This look feels very off-duty European to me.
I love the blazers from Veronica Beard and Sezane in particular.
Styling Trousers for Work
Another great alternative for a work ensemble featuring a favorite little tweed jacket. This is my most worn that I own in three colors (!) Size M.
You can shop all my favorite tweed jackets and blazers in the w&w Shop. Adding a chic belt adds a bit of visual interest to an otherwise simple outfit.
Leather Trousers Styled
This is a perfect sleek and simple example of a high-waisted trouser outfit I love.
These are faux leather straight leg trousers from J.Crew that I paired with a cropped cashmere crewneck sweater by Everlane and my favorite Chanel Slingbacks.
Trousers with a Monochromatic Top
One of my favorite ways to style a wide leg trouser is in a monochromatic color palette. I think it looks so stylish and is really easy to put together.
This pair of trousers is by Abercrombie and they are such a good find. I sized up in them.
Trouser Suit Styling
Another semi-monochromatic option for your trousers is to of course pair them with a matching blazer. I love adding a delicate silk tank or a striped tee under mine to make it more casual.
Adding a striped tee makes this trouser outfit a bit more casual.
Trousers with a Sweater Jacket
A pair of comfy wide leg trousers with a little cardigan or sweater jacket is a go-to look for me for International Travel. This allows me to look put together for an overnight flight and then have a good outfit to be wearing if my room isn’t ready to be checked into yet.
The Sezane Betty is my favorite of my collection. I’m wearing a L above with the Aritzia Effortless Pant (size 8).
Related: Easy Travel Outfits
How to Style Trousers Casually
I love styling trousers in a more sporty manner. Adding a baseball cap and sporty sneakers by Converse or Veja is a great way to do this.
Chord makes great baseball caps that are on-trend and so well made.
Trousers Styled with a Knit Tank
Perfect in summer, a light colored trouser pairs well with a knit tank. Don’t forget a chic basket bag to complete the look.
I usually find the best knit tanks at Reformation and Sezane.
Trousers Styled as a Set
I love the effortless appeal of a trousers matching set. La Ligne does some great ones in summer including the one I am wearing above.
. . .
Are you embracing trousers more in your everyday wardrobe? Whether you prefer wide-leg, high-waisted or tailored styles, I hope these trouser outfit ideas help you feel confident styling them year-round.
Are you in on the trouser trend? Furthermore, I’d love to know, which look from above is your favorite?
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