I know that many of my readers join me in desiring to look pulled together, polished and current, but not trendy. Sometimes it’s a fine line between trendy and modern, but my goal is to help us strike that balance so we appear relevant and “with it,” while still feeling true to ourselves and our personal style aesthetics. So throughout the year we’re Styling the Classics for the Modern Woman. Today’s classic? I’m styling the classic black trouser three ways.
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Styling the Classic Black Trouser for the Modern Woman
I’m styling three different pairs of black trousers from my closet. You’ll see me in a pair of straight leg, slim fit pants in four-season stretch from J.Crew, a pair of straight leg pants with a fuller leg from Talbots and a pair of wide-leg knit cargo pants from Veronica Beard. I’d say the first pair is the most classic, the second a little more modern, but still timeless and the third pair is distinctly modern, but still gives those classic vibes. Let’s see how I styled all three so they look current and fresh.
Styling the Classic Black Trouser with a Blazer
Whether you’re still going into the office, you enjoy dressing up for church or you have meetings for which you need to look a little more polished, you can’t go wrong with a coordinated pants and blazer combo. If you are careful to purchase true black trousers and a true black blazer or other jacket, you’ll probably be able to pair them together even if they’re not the same brand.
I’ve paired my J.Crew Kate straight leg trousers with my Veronica Beard Miller dickey jacket even though they’re not even in the same kind of fabric. The key is making sure the color and the intensity is the same. Of course, if you’re investing in either a pair of black pants or a blazer, it’s smart to go ahead and buy the coordinating option, if it’s available.
To make this classic pairing a little more modern I wore it with a bright blue silk blouse and I buttoned it all the way up. Buttoning it up took care of the “what do you do with the collar?” dilemma and it looks very intentional, like you’ve put some thought into styling your look. The pretty blue solid is a more contemporary choice than a print, and it looks timeless. You could choose any color that looks great on you.
I completed the look with minimal but impactful jewelry, cap-toe block heel pumps and a classic black tote. What makes this classic look more modern? The straight silhouette of the pants, the high rise, the length of the pant, the choice of blouse and the buttoning of the collar.
Styling the Classic Black Trouser with Modern Sneakers
One of the ways you can keep your classic black trouser outfit modern is by styling it casually. So if the occasion allows, go casual with those black pants.
Here I’ve still kept the look chic and a little sophisticated by wearing a classic but on trend cashmere sweater with my relaxed fit Southampton trousers from Talbots. These pants feature a high rise (but not too high) and a full length. They’re also available in petite, plus and plus petite sizes.
It looks like I could have used a few swipes with a lint roller. Ha! Yes, a lint roller can be a good friend if you’re wearing black trousers. I usually keep one in a drawer at our front door, in my office and in the car, but I forgot to take one on our trip when we photographed these looks. Oops!
A couple of modern touches in this outfit include wearing a crewneck white t-shirt under the sweater and allowing it to peek over the sweater collar and simply choosing a striped sweater.
And of course another modern touch is wearing my field sneakers with the outfit. They’re comfortably and sporty, and EVERYONE is wearing sneakers for all sorts of outings these days. They are an extremely modern choice. I did indeed wear socks, choosing them in a slightly contrasting grey – not black (to match the pants) or ivory (to match the shoes). See this blog post for modern tips on wearing socks in the winter. Another modern choice was to wear a classy, long wool double-faced coat rather than something more casual. This particular style formula is very on trend right now, but it still looks classic and pulled together.
Styling the Classic Black Trouser for a Fun Date Night
This last outfit is what I wore for our recent date night to celebrate our 37th wedding anniversary. I wanted to look a little dressed up, but also very current and relaxed.
These Veronica Beard full length, wide leg cargo pants are definitely a little pricey. But they were a fun addition to my wardrobe to keep it modern and fresh.
While I definitely advise first investing in pieces that are truly classic, it’s also smart to add a few things to your closet that will make it easier to create distinctly modern looks. We don’t need all the bells and whistles, but we definitely need at least a few if we desire to look contemporary.
Another modern choice I made in this outfit was to wear a casual button-up shirt under my grey cashmere sweater. This particular shirt is so soft and comfortable, making it easy to wear under a sweater. And speaking of the sweater, wearing one that is “cropped” in length and fitted at the waist was crucial with these wide leg trousers. A looser fit or a longer length in the sweater would have lost the slenderizing effect and great proportions of these trousers.
I completed the look with black pointy toe booties C/O (use code KAYBOOTS for $50 off your first pair of Ally boots), a grey wool coat and a splash of red.
I’ve got a couple of style boards with additional ways to style classic black trousers for modern looks.
Style Board #1
I absolutely adore a column of black under any other neutral or color. Not only is this look slimming, but it always looks chic and a little sophisticated.
The key is to wear black neck to toe. So we’ve combined a black turtleneck with those Talbots Southampton pants and the Ally Boots. You could interrupt the column with a belt if you’d like, but I generally prefer to keep that in black too. Of course, you really don’t need to tuck the turtleneck in this outfit because you’re creating a slenderizing column under the camel trench coat.
Style Board #2
And for our second style board I’ve created a look with a colored sweater, something I wasn’t able to squeeze into the looks I modeled. This one-two punch is a no-brainer until you have to choose outerwear and shoes. That’s when this simple outfit formula can fall apart.
For the most modern and failproof look, I suggest wearing black booties and topping the look with a black coat or a coat in the color of the sweater. Those choices will work for you every time.
Thanks so much for stopping in for a little style inspiration. Remember, you can always find all of the posts in this series in the top menu through the tab labeled 2025 STYLE SERIES.
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Blessed for My Day
As I write today’s post, horrible fires are burning through residential and commercial parts of southern California. It breaks my heart when people just like you and me lose so much and, undoubtedly, feel helpless and scared. What can we do when we see such bad things happen to other people?
I think it’s appropriate to pause and hurt for them, first of all. The things that break God’s heart should also break ours, and we know He is compassionate and loving. And that thought should lead us to pray for them, trusting that God is with them and will make Himself known if they will only seek Him in these difficult times. Finally, we can do something, if we have the resources and the ability. That’s not always the case, of course. But when tragedy hits closer to home, we can show our concern and love through even small acts of kindness.
Rejoice with those who rejoice, and weep with those who weep. ~ Romans 12:15
Love the devotional message. Black trousers have always been a staple in my wardrobe. I have different styles. Recently I added black trouser jeans. Thank you for all the styling tips to help me style them.
I especially like the first outfit and both the style boards! I love boots for winter.
Even when I’m not expecting it, you have something for me to learn or be reminded of! Thank you!
I love this post! I start most outfits with black pants. Nice variety of examples and I love the boards, too.
Thank you, Kay, for this post. I’m not a jeans wearer so love that this one is devoted to trousers!
Yes, the fires in Calif. are just terrible. I live in Oregon and many fire departments from here have sent trucks and men yesterday to help. My husband just retired from 49 yrs. in the Fire Service on Dec. 31st and his department is sending some. I’ve been praying and just can’t imagine what they are going through and will in the coming months/year. I know God is in control and you are right, if we have the resources to help, we need to, whether financially or physically etc. My husband has always been so cautious to be ready for our area (Oregon) wildland fires that have been more often these last years and we have resources on our property to help if needed. We were just talking, that during wildland season its hard to leave home on vacation, wondering what could happen, but we can’t live in fear. Great post and good ideas. I’ll save this.
Love your daily posts! I noticed all the different lengths on the trousers. I get so confused as to how long they should be and with what shoe. We can’t have that many shoes or pants. Plus the costs of constantly changing lengths is stressful. Once you tailor them there is no going back. Trends are always changing. What would you suggest?
Really every length looks current and stylish right now, so choose the ones that work best for you. During the winter if I’m going outside I usually wear full length that I can wear with boots or shoes and socks. During the spring and summer and into early fall I almost exclusively wear ankle length. You can wear almost any shoe with an ankle length jean or pant, but if you wear boots you want a tall enough shaft so they go up under the pant leg. I like having jeans in different full lengths that I can wear with different height shoes. I have most of my long pants at a length where I can wear a modest heel or I can wear my sneakers that have a platform heel.