How to Style Dickies Pants Like A Boss Lady

Let’s talk about how to style Dickies Pants (+25 Dickies Pants outfit ideas for inspiration)

The fashion world has constantly shown us that trends are impossible to predict. One day, everyone is wearing military pants with crop tops, and the next day, it’s dickiest pants.

If you’ve been following the fashion world over the past few years, you’ll notice that dickies pants are still very much in vogue. Given its history, however, it’s only natural that many tops don’t match well with them.

In this article, I’ll show you some of the best ways to wear dickies pants for the classiest looks. Below are some outfit inspirations that you should consider copying while styling dickies pants.

How to Style Dickies Pants

Table of Contents

1. Crop Sweater Shirt with Dickies Pants + Sneakers + Chic Bag

What’s a better way to style dickies than pairing them with a slightly cropped sweater shirt. Sweater shirts offer excellent protection against winter cold and so do dickies pants, making both an awesome combo.

Sweater Shirt + Dickies Pants + Sneakers

2. Graphic Tee with Dickies Pants +Sneakers

Graphic tees and jeans are a sure match, but have you tried pairing them with dickies? As evidenced from the model in the picture below, dickies pants are excellent replacements for jeans if you’re only pairing them with a graphic t-shirt.

Graphic Tee + Dickies Pants +Sneakers

3. Graphic Crop Top with Dickies Pants + Black Boots + Sunglasses

This crop top may not make excellent workwear, but it does match nicely with those dickies. If you can replicate this outfit perfectly, you can wear it to any event that’s not formal.

Graphic Crop Top + Dickies Pants + Boots + Sunglasses

4. Inner Vest + Oversized Flannel Shirt with Dickies Pants + Sneakers

Wearing an oversized flannel over skimpy inner vests seem like the correct combination, but finding pants to match may be tasking. Fortunately, you shouldn’t have to sweat over it anymore; just wear dickies and move on.

Inner Vest + Oversized Flannel + Dickies Pants +Sneakers

5. Sweat Shirt with Dickies Pants + Sneakers + Handbag

It doesn’t matter what kind of clothing you’re trying to style, there’s always a way to make it a gorgeous all-black outfit. In the case of dickies, this model encapsulates how the perfect all-black dickies outfit should look.

Sweat Shirt + Dickies Pants + Sneakers + Handbag

6. Peach Shirt + Blazers with Dickies Pants + Loafers + Handbag

If you’re after an outfit that’s perfect for work, here’s your best bet. However, the appropriacy comes at the expense of its chicness. Don’t show up like this on a night out or at a friend’s birthday, please.

Peach Shirt + Blazers + Dickies pants + Loafers + Handbag

7. Sport Bra with Dickies Pants + Shoes

Sports bras can look awesome with any other clothing material if you get the colors right. That’s exactly what she did right here, making the entire outfit look matched from heaven. If you’re looking to show more skin than a crop top can, here’s your best bet.

Sport Bra + Dickies Pants + Sneakers

8. Crop Tank Top Vest with Dickies Pants + Converse Shoes

An outfit idea has proven that this combination works but in dark colors. If you prefer lighter colors for your outfits, here is a casual inspiration on which to base your next dressing.

Crop Inner Vest + Dickies Pants + Sneakers

9. Tank Crop Top with Hybrid Dickies Pants +Chunky Sneakers + Cross Bag

All dickies pants look awesome but hybrid dickies pants are just on another level. Just take a look at this outfit, look me in the eye, and tell me you’re not going to consider recreating this someday.

Strapless Crop Top + Hybrid Dickies Pants +Chunky Sneakers + Cross Bag

10. Centred Zipped Shirt + Biker Jacket with Loosely Fitted Dickies Pants + Sneakers

If you fancy fashionable outfits, here is a cute outfit inspiration for you. Since the pants aren’t ripped and the shirt isn’t too skimpy, it qualifies well for a work outfit, barely.

Centred Zipped Shirt + Biker Jacket + Loosely Fitted Dickies Pants + Sneakers

11. Long Sleeve Shirt with Dickies Pants + Knee-High Boots

If you’re into all-black outfits, here is another way to style dickies pants to inspire you. My favorite part of this outfit is the smile, but the shirt doesn’t look bad either. This outfit will appeal to conservative dressers since it covers almost every inch.

Long Sleeve Shirt + Dickies Pants + Knee-high Boots

12. White Inner Vest + White Long Sleeve Shirt with Dickies Pants + Shoes + Handbag

All-black outfits are cool, but have you seen an all-white outfit with dickies pants yet? Here’s one, and it simply doesn’t cease to amaze me. Feel free to copy it and try to be as creative as possible.

Inner Vest + Button-down Shirt + Dickies Pants + Sneakers + Handbag

13. Graphic Shirt with Flared Dickies Pants + Sneakers

Yes, flared dickies pants are a thing, and thanks to her, we now know that you can also pair them with graphic tees. I’d prefer matching the colors to create similar levels of chicness.

Graphic Shirt + Flared Dickies Pants + Sneakers

14. Graphic Tee + Jean Jacket with Army Dickies Pants + Black Boots

Matching a jean jacket with army-printed dickies pants takes chicness to another level. It’s crucial to warn you to copy this outfit with caution as it can get pretty addictive.

Graphic Tee + Jean Jacket + Army Dickies Pants + Boots

15. Sweatshirt with Loosely fitted Dickies Pants + Sneakers

It’s hard to find outfits that go badly with hoodie-like Sweatshirt, and dickies pants are not an exception. You can switch up the colors or add additional apparel, but you must also ensure that you’re not changing anything drastic in the outfit.

Hoodie + Loosely fitted Dickies Pants + Sneakers

16. Crop Top with Dickies Pants + Nike Sneakers

This isn’t the first time that we’ll see a dickies pants and crop top, but the multicolored nature of the top simply makes it look better. This outfit appears better in outdoor sceneries and the sneakers are especially chic.

Sports Bra + Dickies Pants + Chunky Sneakers

17. Graphic Tank Top with Dickies Pants + Sneakers

A strapless graphic top takes a lot of confidence to wear, but when you do, it always looks amazing. The fact that the inscription on the shirt reads dickies is awesome, given that she’s wearing dickies.

Graphic Strapless Top + Dickies Pants + Sneakers

18. Graphic Sweater with Dickies Pants + Sneakers

If you’re afraid of styling your dickies incorrectly, simply wear it with a graphic top. It’s almost impossible for a graphic top and dickies combination to go wrong. And as she proved with her outfit idea, cropping the outfit a bit won’t hurt.

Graphic Crop Top + Dickies Pants + Sneakers

19. Inner Crop Vest with Dickies Pants + Trench Coat

If you’re going on a visit to the beach, dressing this way only comes naturally. The trench coat can easily go off when you need some air and you can put it on again to regain her elegant look.

Inner Crop Vest + Dickies Pants + Trench Coat

20. Crop Top + Leather Jacket with Dickies Pants + Boots + Sunglasses

If you’ve noticed, this list doesn’t include an outfit with sunglasses yet, but here is an excellent idea to prove that sunglasses work with dickies. Try retaining the color match to look just as chic as she looks in this demonstration.

Crop Top + Leather Jacket + Dickies Pants + Boots + Sunglasses

21. Crop Long Sleeve Top with Dickies Pants + Sweat Cap + White Sneakers + Clutch

A cropped long sleeve top also proves to pair excellently with dickies pants. The sweat cap integrates perfectly into the outfit and the white sneakers are just excellent.

Crop Long Sleeve Top + Dickies Pants + Sweat Cap + Sneakers + Clutch

22. Crop Tee with Dickies Pants + Shoes

Again, another crop tee that slightly dabbles into the territory of graphic tees. While it isn’t the best gym outfit, it’s just perfect for slight walks or cruises on your scooter board.

Crop Tee + Dickies Pants + Sneakers

23. Sweat Shirt with Dickies Pants + Converse Shoes

This is my personal favorite of all the outfit ideas in this collection. It’s perfect for keeping the cold out in the winter, and it’s also a decent work outfit. In addition to that, it doesn’t look bad, although, it’s not the best Christmas outfit either.

Sweat Shirt + Dickies Pants + Sneakers

24. Black Shirt + Jacket with Dickies Pants + Trainers + Sweat Cap

Except for the red sneakers, this is another all-black dickies outfit. Since we’ve already discussed why this works every time, I don’t think we have to go over it again.

Black Shirt + Swead Jacket + Dickies Pants + Swead Sneakers + Sweat Cap

25. Oversized Sweater with Loosely Fitted Dickies + Nike Sneakers

An oversized sweater with loose dickies makes a great and fashionable winter outfit and they shouldn’t break the rules at your workplace. Copy the colors precisely and you’ll look just as great as she does here.

Oversized Sweater + Loosely Fitted Dickies + Chunky Sneakers

And that’s all for my post on how to style Dickies Pants. Want some more outfit ideas? Then you might want to check out these blog posts.

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How To Style Dickies Pants