I often hear clients or friends say that they would love to wear dressy pants, but they are too dressy for their lifestyles. Despite casual pants fatigue, jeans and utility pants are their go-to option. Over and over again, I find myself explaining that dressy pants can be effectively dressed down with a casual support act. 

The collection shows examples of how dressy pants have been dressed down by combining them with casual shoes. That’s not the only way to create a more casual vibe, but it’s a very effective one. 

Shopbop
Custommade Ena Pants
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Shopbop
Ganni Suiting Pants
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4
Boden
Exeter Wide Leg Pants
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2
Shopbop
IRO Nux Trousers
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2
Mango
Slit Hem Pants
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2
Zara
Belted Paperbag Pants
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Zara
Chino Fit Pants
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Mango
Paper Bag Trousers
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2

Here are six outfit creation strategies that incorporate casual items to dress down dressy pants.

1. Fashion Sneakers

Sneakers are the shoes of our fashion era, and the easiest way to dress down a pair of dressy pants. My preference is for fashion sneakers, but athletic sneakers can look great too. White sneakers are classic but feel free to wear any colour, with or without white soles.

2. Casual Oxfords or Cowboy Boots

Think flat or low-heeled chunky casual oxfords with or without platforms, or low-heeled cowboy boots or shooties if sneakers aren’t your thing. The oxfords can be solid or patterned, and feel free to pattern mix. The oxfords work particularly well with wide crops, while cowboy boots work well with full-length bootcuts or flares.

3. Chunky Flat Boots or Dr. Martens

Flat boots with higher shafts and VERY chunky soles (think Dr. Martens) are an excellent way to dress down dressy pants. Boots with chunky lug soles or haute hiking boots can work well too. Black boots are one way to go, but patterned, red, cognac or white boots get my top vote.

4. Casual Knitwear, Tees or Sweatshirts

Knitwear with a chunkier gauge and/or slouchier fit creates a more relaxed vibe. The same goes for a tee, graphic tee, or welted sweatshirt. Combining those types of tops with dressy pants with the casual footwear discussed above is an easy outfit formula.

5. Denim Component

Adding denim to an outfit is the easiest way to dress it down, but you need mild and warmer weather to be comfortable. Think denim shirt, denim jacket or denim blazer, and Bob’s your uncle. Feel free to throw on casual shoes too.

6. Sporty Puffer, Aviator, Utility or Moto Topper

Short non-athletic puffers look great with dressy pants, especially when the footwear is casually complementary. If puffers aren’t your thing, think casual toppers like moto, utility and aviator jackets in tailored and oversized fits. These are warmer and cosier than denim jackets.

You can also throw in casual bags like hobos, backpacks, belt bags, or crossbodies, and casual headgear like tweed newsboys, caps and beanies. But these come off indoors so be mindful of that.

I LOVE wearing dressy pants, and thoroughly enjoy dressing them both up and down. My favourite ways of dressing them down are with low and hi-top sneakers, a denim jacket in mild weather, casual knitwear, an aviator or short puffer, and crossbody bag. In cold weather I’ll add a fun beanie or beret. I also like to combine dressy pants with a relaxed fluid tucked shirt with scrunched sleeves. I will definitely be embellishing my dressy pants capsule since I find the item extremely versatile, and one way to give blue jeans a well deserved rest.

GOLDEN GOOSE Yuri Quilted Leather Down Jacket

Freya Checked Relaxed Straight Trousers