Curious on how to style trousers now that they are seemingly everywhere? The menswear inspired bottoms have had a resurgence of late and as such my collection of favorites has grown and I so enjoy styling them to make them align with my own personal aesthetic.
Truth be told, up until a couple years ago I was a jeans girl through and through. Every now and then I add in some other patterns or fabrics like a pair of J.Crew Plaid Pants during the holidays or a pair of Corduroy Wide Leg Pants but nowadays I really love wearing trousers – particularly high-waisted trousers, straight leg trousers and wide leg trousers.
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
Trouser Outfit Ideas
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 are my all-time favorite and most worn (I sized up to an 8 for a more slouchy fit). I love that they pair so well with ballet flats, sneakers and a lower heel (I am 5’5″ for reference). When paired with a ballet flat, this is an outfit that I often wear for meetings.
To add some visual interest, I added a sweater with button details along the sleeve and a favorite belt.
Related: Ballet Flats Outfit Ideas
With Sneakers
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. This pair is my most worn.
With a Tweed Jacket
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.
With a Turtleneck
If you’re a turtleneck fan for Fall and Winter, pair your favorite style with a trouser.
I like this one above because it is slightly cropped so it doesn’t look like I’m swimming in this look. You could also add a belt to the above look as well.
With a Cropped Crewneck and Slingbacks
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.
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.
This pair of trousers is a great affordable pair by Uniqlo if you want to dip your toe into the trend without spending too much. I would recommend sizing up.
Linen Trousers
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.
I love the linen by Faherty – they make my linen button down (M) and linen pants (M) above.
Reformation always has good linen pieces, too.
Monochromatic Outfit
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.
As a Suit
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.
Above I am wearing this great blazer (size 6) and the matching trousers (size 8 and had them hemmed!) and this striped tee (size M).
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! You can use code WIT&WHIMSY20 for 20% off your first order with the brand.
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 (see below!)
With a Short Sleeve Sweater
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.
I also own the Alanya Pant by the brand in an 8.
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.
With a Car Coat
As you head into Winter weather, a classic car coat makes a great topper for trousers.
Just ensure it is the right length so your proportions are aligned.
Tuxedo Dressing
Have a dressier event or something black tie and want to lean into a more menswear ensemble? Enter, tuxedo dressing. Add a chic, either very fitted or oversized tuxedo jacket with a tailored tuxedo pant and you’ll have a show stopping outfit.
With a Baseball Cap
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.
Silk Trousers
Silk or satin trousers are the easiest way to be elevated yet comfortable. 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. Comfortable and yet slightly dressed up. I wear them for evenings with heels once I’ve arrived in a destination or dress them down with ballet flats or sneakers like below for a day spent exploring.
I love the Varley satin pants in particular (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.
Plaid Trouser Outfit
Like a little pattern play? Consider a black and white check like above. This plaid pair is by French brand Sezane.
Related: The Best Sezane Essentials.
With Striped Knits
In winter and colder temperatures I often pair my trousers with oversized cozy striped knits. My favorites are from Sezane and La Ligne.
With a Knit Tank
Perfect in summer, a light colored trouser pairs well with a knit tank. I love the fabric 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 paired them with a Reformation knit tank (size XL). I like this one and this one as well.
. . .
Are you in on the trouser trend? Which look from above is your favorite?
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