How to Wear Menswear Inspired Plaid Pants to the Office

Wear to Work Plaid Pants

Key Piece: Plaid Flair Leg Pants, $137; Outfit 1: Blazer, $69; Tank, $26; Earrings, $119; Bracelet, $20; Pumps, $198; Bag, $378; Outfit 2: Sweater, $180; Shoes, $180; Earrings, $30; Bag, $450

Wear it to Work: Nordstrom Plaid Flare Leg Pants

I love how today’s post came together. Plaid pants are such a classic, but if not done in a modern silhouette, it can look a bit dated. Classique Entier is Nordstrom’s private label brand that offers contemporary, business-appropriate separates and suits. It’s ideal if you want better pieces at reasonable prices. Their items have lasted for years in my closet. When I came across these plaid flair leg pants , I knew I had a winner that didn’t look like a lot of the same.

Before we even get started, can we talk about the length of the pants in the picture? It’s terrible. If you are going to wear menswear-inspired pants, you have to follow traditional menswear rules.  The hem of these pants needs to break at the top of your shoe. They are way too short in the image, so figure out your ideal heel height and have them altered accordingly.

For the first outfit, I pulled the black out of the plaid. This blazer is from J.Crew Factory and miraculously comes in sizes 00 – 20 in both missy and petite. Do you know how hard it is to find a classic blazer in sizes above 12? It’s hard, so if you need one, give this a try. It’s under $100 and comes in three colors. Because I wouldn’t take off the blazer, I layered it over a basic, fitted tank by Hinge.

Because the buttons of the blazer are gold, I paid attention to the hardware of the bag. Remember, matching hardware creates a cohesive look. If you don’t want to have to worry about such things, you can replace the buttons with simple black ones. For this post, I showed more serious investment kind of bags. I don’t usually love Kate Spade, but this bag is gorgeous. It’s roomy, is super chic, and is a great everyday work bag.

To round out the look, I wanted old-school gold button earrings with a little edge and found that in these. A simple goldtone link bracelet will peak outside the sleeve of your jacket. Finally, a suede black d’Orsay pump balances the weight of the jacket while still giving you a heel you can walk in.

Our second look is cozy and sophisticated. Nordstrom has a line of fabulous cashmere at reasonable(ish) prices (considering it’s cashmere). I love the slouchy feel of this light-gray sweater and the interest in the bell sleeve. It’s not overly dramatic, but definitely trend-focused.

I don’t think you need much else here because the interest is in the plaid paired with the texture of the sweater. I picked these updated hoop earrings (under $30) to give some movement. A comfortable suede wedge gives height while keeping the look on the casual side.

I found this gray satchel from Henri Bendel, and I’m out of my mind for it. I’m going to buy it for myself at our next little Henri Bendel shopping party. It’s updated, classic, and just all-around gorgeous.

Finally, if you picked up the Banana Republic tie front cardigan that we featured last week, it would look perfect with these pants!

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

  1. I love the plaid pant , blazer and tank outfit for work. Can you recommend another type of shoe beside the pump? Also can you recommend a different tank or shell?

      1. Thanks Megan!
        I have been following you for 3+ years! I look forward to your email every day! I am 52 and your outfits and suggestions are perfect.

        I adore your comments, posts, instagrams, etc about parenting and your girls. Enjoy them – your time with them will fly by! My youngest just went off to college last week – life doesn’t prepare you for the day you drop them off.

        So looking forward to upcoming challenge.

        1. Thanks for your kind words Amy! I’m excited for the challenge too! And, yes, time is already flying with the girls. My Maddie is wearing the “big girl” uniform for school. She’s been looking forward to it since 1st grade 🙂

  2. A photo of the correct length for these pants would be so helpful. I need to have mine hemmed just a bit but if they come back looking like the model I will cry!

    The Wear to Work post have been excellent! I picked up several pieces for fall.

    1. Thanks Samantha! I think I need to do a series on fit, and show the guidelines for different pieces. That’ll take some time to pull together. For now, you want to first determine what height heel you are going to wear with your pants and take those shoes to the tailor. Next, tell the tailor you want a “break” on the top of your shoe. They will understand this to mean you want your hem to slightly puddle on the top of your foot.

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