An Updated Way To Style Your Best Pair Of Tailored Trousers

For a long time, we were styling trousers to be a part of business wear or at least more formal wear. Women often felt compelled to wear their trousers as part of a suit and weren't experimenting with other ways to wear them. Thankfully fashion and style rules are continually evolving and in reality, these pants can be worn with just about anything and for any occasion and look amazing.

A good pair of tailored trousers can be styled in an endless myriad of ways, depending on the look and feel you're trying to achieve. Whether it's for a more formal event or a casual, relaxed look for running weekend errands as an alternative to leggings or joggers, trousers aren't just for office wear anymore.

From wearing them with jackets and blouses to stilettos or running shoes, trousers can be one of the most versatile staple pieces in your wardrobe. If you're in need of a little inspiration, here are some updated ways to style your best pair of tailored trousers.

Keep it simple with Mary Janes

Mary Janes is a shoe trend that will be everywhere this spring, proving that comfort and style can go together. Our feet couldn't be happier! Mary Janes are a great shoe to wear with a pair of tailored trousers as long as they aren't too long. If they are, you'll want the hem to sit just at the ankle. A slightly tapered pant leg will showcase your beautiful shoes best.

An oversized bomber adds dimension

Normally we associate trousers with structured looks which is why it's so fun to wear them with some oversized pieces, like a leather bomber jacket that is loose and casual. The jacket will give your outfit an edge while still being dressy enough for the office, especially when worn with round-toe ballet flats and a classic handbag. Choosing a wide-leg fit for your trousers will also make it easy to transition the look from day to night.

A strappy shoe and denim trench is unexpected

If you have been looking for a sign to go buy that denim trench coat you've been coveting, this is it. Trench coats are a style staple in those transitional months because they are fashionable and functional. When worn with a pair of khaki-colored trousers, the look gives off an effortlessly classy feel. Style it with a pair of strappy heels and a simple top and this will quickly become a favorite outfit in your rotation.

Keep it classic

Why mess with a classic? If you've got a great pair of pinstriped trousers in your closet, you can style them with almost anything, but there's nothing like a crisp, white button-up and shoes of your choice to create a timeless look. A few minimal accessories are all you need to complete this outfit.

White tennis shoes forever

Whoever is responsible for the rise of the white running shoe, we'd like to thank them! You no longer have to wear uncomfortable heels to be fashionable. Pleated trousers look like they were made to be worn with white tennies and pair well with a boxy sweater. A cross-body bag is the ideal accessory for work or play.

Douse yourself in color

As much as we love neutrals, it's so nice to see monochromatic outfits with color! A fitted floral blouse in coordinating colors looks great with tailored, cropped lavender pants. The shorter length allows you to showcase your shoes, while the color gives the outfit a light, airy feel that's perfect for spring or summer.

Show some contrast

For work or play, trousers can do it all! Elevate your everyday casual outfit with a pair of trousers featuring a stripe down the side. Wear them with a pair of running shoes and a quarter-zip sweater for a put-together look. Pairing black and white together is always safe but we love how the stripe on the trousers adds a bit of interest to the classic color combination.

Pair with a leather moto jacket

Dress up your leather motorcycle jacket or dress down your tailored trousers when you wear these two items together. You may not have thought to wear these two different wardrobe items together, but they really do complement each other wonderfully. A basic white tee is all you need to complete this look.

Go casually cropped

When you look at your trousers in your closet you may initially think of more formal shirts or blouses to wear with them, but a cute cropped tee is a great choice for a casual look. Get yourself used to the idea that trousers are a nice alternative to joggers or jeans for a look that is still relaxed but also smart looking.

Make it monochrome

Not sure what to wear with the pair of gorgeous trousers sitting in your closet? Why not make it a monochrome look by choosing other wardrobe items like a top, blazer, and boots in coordinating shades? The benefit of putting together the perfect monochromatic outfit is that once you identify your primary color (edgy black, calm beige, or head-turning red), the variety of shades and textures you can choose from there are endless.

Say hello to weekend vibes

If you find yourself a pair of trousers that are just the right combination of chic and casual, you know you've hit the jackpot. They can be styled so many different ways, depending on the event or occasion, but we love them when paired with a cute crop top, a blazer, and running shoes. Swap out the shoes for heels and replace the crop with a structured blouse to instantly go from running errands to a board meeting.

Choose a classic white button-up

When in doubt, reach for your crisp white button-up We've already told you that this wardrobe item will be the fashion staple you can't ignore in 2023, and wearing it with a pair of tailored trousers is just one way to style it. Opt to wear yours open over a fitted, cropped tank in the same color, or wear it buttoned up and tucked in for a more traditional look.

Get comfy in a cardi

Cardigans are a closet necessity that are just as versatile as a good pair of trousers. Add some coziness to your look while keeping it office appropriate by wearing a belted cardigan over a pair of leather trousers. You'll want to look for a more fitted and less bulky cardigan to keep this look streamlined.

Define your waist with a belted blazer

Add some contrast to your outfit but still keep it neutral by wearing a cream blazer over a black turtleneck and a pair of classic black trousers. Black is an easy color to match when wearing separates and the cream adds a nice contrast without feeling like it's taking over the outfit. Adding the black belt to the blazer adds some structure to the entire look.

Throw on an overcoat

A classic coat can elevate any outfit. Not only will a long wool overcoat keep you warm when it's cool out, but it adds a flair and sophistication to your whole look. A bright-colored shirt works well with neutral-colored trousers for a foolproof combination that's stylish and simple.

A boss lady look demands attention

Sometimes, simple is the way to go when styling your tailored trousers. After all, a great pair of leather pants don't need much else to make them and you look stunning. You won't need anything other than a crisp white button-up to give boss babe vibes with this outfit. The styling may be simple, but the results are anything but.

An oversized fit is in

Even when you are going for the oversized look, making sure the fit of your trousers is spot on is the key to creating a great outfit. Wide-leg trousers won't overpower you when the fit is perfect. Worn with a loose sweater tucked in at the waist gives this outfit a nice silhouette without having to be tight or uncomfortable.

Don't underestimate a pop of color

You will never go wrong wearing all black, especially with a pair of tailored trousers. The look is classic and black is the one color that seems easier to match than most. A great pair of black pants are so versatile that it looks good with anything, but we love a pop of color to add interest to a more simple look, such as a pale blue shirt.

Dress it up or down

A good pair of trousers can quickly become one of your go-to wardrobe staples because they can be dressed up or down, like pleated, straight-leg pants. They can also be worn for a variety of seasons, making them one of the most versatile pieces of clothing you'll own. A black V-neck sweater over a t-shirt works nicely tucked into dark brown pants with a wool blazer for cooler days. For warmer weather, simply ditch some of the layers.

Add a denim blouse

Welcome spring with a pair of white, wide-leg trousers. The high waist and width of the leg will help elongate your silhouette. Pair with a denim chambray blouse — so on-trend this year — and neutral accessories are all that is left to complete the perfect Sunday brunch outfit.