How to Style Trousers

October 25, 2023

Bash Blazer + Striped Tee + Black Trousers and Converse - Winter Paris Outfit

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. 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. 

Today’s post is designed to help give you outfit inspiration for wearing trousers and you can shop my favorite styles that I own.

How to Style Trousers

Trouser Outfit Ideas

J.Crew Trousers Paris Outfit

With Ballet Flats

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. 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

Cafe Pigalle Paris Khaite Sneakers J.Crew Trousers Fall Outfit

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.

With a Tweed Jacket

I love this look for meetings and adding a belt gives it a bit of additional visual interest. 

Fall Capsule Collection with M.M.LaFleur

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. You could also add a belt to the above look as well.

Fall Winter Paris Outfit featuring Cropped Everlane Sweater with Vegan Leather Pants

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 and my favorite Chanel Slingbacks.

Bash Blazer + Striped Tee + Black Trousers and Converse - Winter Paris Outfit

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 plain tee. This look feels very off-duty European to me.

This pair of trousers is a great affordable pair by Uniqlo. 

Chocolate Brown Outfit for Fall

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. I usually do it with all black but given this year’s Fall Trends, I couldn’t resist pairing chocolate brown trousers with a chocolate brown cashmere sweater.

This pair of trousers is by Abercrombie and they are such a good find. I sized up in them.

Paris Cafe Outfit

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!

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. 

Fall Date Night Outfit featuring Faux Leather Pants

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

Paris Outfit in Fall - Aritzia Trouser

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.

I also own the Alanya Pant by the brand in an 8. 

Fall Capsule Collection with M.M.LaFleur

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.

Fall Outfit Inspiration with J.Crew

For Work

Add a pair of heels and a little cardigan with details like gold buttons alongside your favorite work tote and you have a good work-ready outfit. The above outfit would be perfect for a big work meeting or conference. 

Trousers Outfit

With a Tweed Jacket

Another great alternative for a work ensemble featuring a favorite little tweed jacket. 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.

Plaid Pants Holiday Outfit I wit & whimsy

Plaid Trouser Outfit

Perfectly preppy and festive for the holidays, I love pairing a plaid pant with a favorite sweater and heels during the holiday season.

Not into a colorful plaid? Consider a black and white check like below!Sezane Fall French Girl Outfit

This plaid pair is by French brand Sezane. Related: The Best Sezane Essentials.

Paris Winter Outfit

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.

I am also very into satin trousers right now. I own this casual pair in size M and this pair as well in size M. 

. . .

Are you in on the trouser trend? Which look from above is your favorite?

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