10 Easy Ways to Wear Black Dress Pants to Work

If there is one item sure to be hanging in all of our closets, it’s a pair of black dress pants.


Classic Bootcut Pants 

Tank, $40 | Tweed Blazer, $70 |  Tweed Blazer, $70  |  Bag, $450  |  Pants, $109  |  Wedges, $30  |  Earrings, $68 


Easy Ways to Wear Black Dress Pants to Work

Thankfully, bootcut pants are making a return to retail. For years it seemed our only option was skinny ankle pants – and they are still very much in style, but now, we have an alternative. 

You want to look for “bootcut” trousers specifically. “Wide leg” will most likely be too dramatic for work and exaggerated for your body type. Bootcut is just right because the leg opening is subtly flared. It’s the flare of the bottom that creates a lovely proportion. Essentially a bootcut balances out your shoulders and hips. It’s an ideal cut trouser if you are curvy and/or have broad shoulders. 

Today we’re using a navy (also available in black)  trouser from Talbots appropriately called “barely boot pants.” They are done in seasonless wool which means they will feel substantial and you can technically wear them all year long.

They are also fully lined – I know, it’s like finding a unicorn. Even better is that they are available in all sizes including petite, tall, plus and plus petite.  

If you need some fresh suiting pieces, it’s a good idea to pick up the coordinating jacket, available in the same color and sizing options. For some tips on how to create a small capsule out of your basic suiting, check out our recent post here

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You can see all the suiting options here: 


Pants, $129 | Jacket, $149 | Bag, $495 | Tank, $68 | Wedge, $45 | Earrings, $1450

Take a look at  these pants on the model. They are too short. You want the hem to puddle ever so slightly on the top of your foot.  On the model, I would bring the hem down 1/4 – 1/2″.  The tailoring on any bootcut pant is crucial to creating a tailored look.  If it’s too short the flare will open at the wrong part of your leg, and if it’s too long, it will look oversized and sloppy. Have them hemmed to fit you properly, it’s an easy fix. 

I added a statement jacket in a nubby tweed. It’s nice to pair a dark bottom with a lighter top, it’s another way to look long and lean. DKNY at Macy’s as an array of well priced (under $150) separate jacket options. 

Here’s what you need to know about wearing a bootcut pant: your top needs to be fitted to your body (doesn’t have to be skin tight) and if you’re wearing a jacket, the bottom of it should stop at your hip bone. Chances are if you wore a blazer any longer than hip bone the entire look will overwhelm you. 

I really like this layering tank by Elie Tahari (also available in black). You want to wear a scooped neckline with a collarless jacket. I don’t know why but so many websites do a terrible job styling their merchandise pictures. Don’t wear a shirt that allows the neckline to sit above the neckline of the jacket.

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For shoes, you can wear a pair of pumps, but you might also consider a wedge. These by Nine West are only $45.  A wedge with a bootcut are a perfect pairing because the weight and shape of the wedge balances the width of the leg. 

I went the splurge route on accessories. I’d rather have one gorgeous pair of earrings that I wear every day than a tray full of inexpensive costume pieces.  These gold hoops by David Yurman are simple gorgeous. If you are waiting for a special occasion to wear your better pieces, let me encourage you to go get them and put them on immediately. Life is too short to be waiting around for a place to wear you better jewelry. 

Finally, this navy bag by Gigi New York just made my personal wish list. You can’t go wrong with a high quality, classically shaped bag in navy. I so appreciate it not being covered in logos, BUT you can have it monogrammed which makes my preppy heart sing.

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10 Easy Ways to Wear Black Dress Pants to Work

4 thoughts on “10 Easy Ways to Wear Black Dress Pants to Work”

  1. Do you have any suggestions for nice earrings (small gold hoops, studs) that are quality but not over $1000? I’m looking more for $100. Is that automatically going to mean cheap junk?

    • Hey Sarah, It doesn’t necessarily mean “junk.” We’ve featured many more affordable options over the last year. If you want real gold, I would look to a local jeweler in your neighborhood. They tend to have a nice assortment of basic gold hoops and a range of prices. Plus, you’d be supporting a local business.

      QVC is another option, I frequently wear these inexpensive studs.

      If you wanted a better costume piece, I’d go with something like these Kenneth Jay Lane hoops.


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