Denim Jacket Outfits: 4 Ways to Reimagine Your Trusty Jean Jacket

What to Wear with a Denim Jacket: Raiding the Closet
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Last Updated on June 18, 2022

Be it cropped, distressed, oversized, or embellished… the denim jacket is a pillar of women’s fashion for decades.

Britney and Justin in Double Denim

The allure of this timeless staple lies within its versatility, considering you can wear it for a night out, a date, brunch, or even a Halloween costume (queue Britney Spears and Justin Timberlake circa 2001).

When I think of my favorite denim jacket, my mind always fixates on my mom’s vintage denim varsity jacket. Although it’s not the most traditional of the denim-outerwear family, it has transformed several of my favorite outfits into ones that highlight my personality and edge.

Of course, I have some other favorites in my collection too: namely, my light-wash and oversized Levi’s jean jacket. Combining this piece with a tight mini dress and my platform Doc Martens is, well… *chefs kiss*, but it can also be worn a plethora of different ways, too.

The point being: a classic jean jacket can completely reimagine some of our most frequently-worn outfit combinations. Do you need a fresh look for a casual coffee shop date with a friend?

Are you interested in elevating your Sunday errand ensemble? Or, are you just looking for any reason to pull out that old dusty jean jacket from your coat closet? Whatever your motivations may be, I’ve got you covered.

#1. First Date Vibes

When on a first date, the best plan of action is to show up as your authentic self: personality, quirks… the whole lot. 

I completely encourage the idea of branching out and wearing eye-catching clothing in order to set the tone for how you want to present yourself to the person sitting across from you at dinner or drinks. Conversely, I also respect and appreciate the idea of wearing something familiar… something that you know you’ll look good in, every single time.

Herein lies the inspiration for Outfit #1.

Denim Jacket Outfit for First Date

Denim Jacket (American Eagle) | Bodysuit (Reiss) | Chelsea Boots (Macys) | Leather Pants (Bershka) | Silver Earrings (Urban Outfitters) | Bracelet (Urban Outfitters)

The one shoulder bodysuit allows for a little skin to show, and the leather pants add an interesting flare via different textures throughout the look. Plus, the right leather pants can be incredibly comfortable, especially if you’re on a more active date. The main character of the look, however, is the cropped and sherpa lined denim jacket.

In the colder months, a fashionable and versatile jacket is almost as valuable as a car windshield scraper (if you’re in a snow-packed area, like I am). Unlike many pieces of outerwear that are tailored more for warmth than for style, this AE jacket ensures that you don’t have to decide between the two.

If you don’t have a fleece-lined denim jacket in your collection, consider switching the sleeveless bodysuit for a long-sleeved turtleneck, and pair it with your favorite cropped coat.

Accessories and shoes are where your personal style can really shine. Here, I’ve complemented the outfit with a pair of comfortable black chelsea boots and some delicate silver jewelry. (Note: I realize that the gold vs. silver debate is deeply personal. I’m actually a gold girl, but for some reason, silver spoke to me for this combination).

The key here is to blend utility with expression. With an outfit like this, you can rest assured that you’ll be warm, comfortable, and look hot for your date. Duh.

#2. Night Out

While blue denim is regarded to be synonymous with “casual”, I truly believe that black denim is the opposite. Black is a color that elevates even the most mundane outfit and pulls everything together, which makes it a perfect accent for a weekend “going-out” look.

As previously mentioned, my favorite way to sport a denim jacket is atop a fun mini dress. When your jacket is a neutral or solid color, add an exciting pattern or silhouette underneath!

Night Out Denim Jacket Outfit

Dress (Pretty Little Thing) | Denim Jacket (MyTheresa) | Boots (Macys) | Earrings (Amazon) | Necklace (Baublebar)

I love this strappy bodycon from Pretty Little Thing, equipped with an underwire bust detail and a lively pattern. So as not to take away from the dress’ boldness, consider wearing the jacket over your shoulders while walking to and from your party destination.

This outfit pairs well with any footwear or accessories, but since my feet are always cold, I opted for a knee-high sock boot. These kinds of boots tend to make the legs look longer, which may be preferable to offset the boxiness of the oversized jean jacket.

Funky platform pumps or black strappy sandals would also add a fancy touch to this tried-and-true nightwear look.

Pair it with your favorite dainty gold jewelry and you have a look that will survive until midnight… or whenever your nights usually end. You do you, girl.

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#3. Sunday Market

Let’s be honest. Every once in a while, we get tired of wearing the same groutfit for our weekly grocery run. I’m perfectly content being seen in my gray sweats and oversized sorority hoodie in public, but sometimes… I feel like showing up and showing out in the frozen food aisle.

Going Shopping Jean Jacket Outfit

Denim Jacket (Nordstrom Rack) | Sweater (Monki) | Flared Leggings | Sneakers (Amazon) | Sunnies (Spitfire) | Tote Bag (Amazon) | Earrings (Truerocks)

Consider combining something comfy (i.e. flared leggings) with something a bit more refined, like this structured knit sweater. You can never go wrong with these neutral tones, and even though you feel snuggly, it looks like a little extra effort was put in.

Layer it with an oversized light wash denim jacket. I love this one from Topshop, because the slouchiness doesn’t look lazy… it looks effortless. In the winter months, it will provide an additional layer on your hot girl walk to the market.

But in the spring, switch the fuzzy sweater for a fitted plain white tee and let the jacket hang off your shoulders to embody the iconic model-off-duty aesthetic.

Pro tip
These elevated aviator sunglasses boost any outfit, casual and dressy alike. I love this style from Spitfire. Choose one of the several color options to add spunkiness to your outfit in a pinch!

90s Sneakers and jean jackets are a historic combo, especially for your more active errands. A clean pair of white sneakers is never a bad decision, and neither is a large tote bag to carry the essentials (phone, keys, wallet), and maybe some snacks that were picked up last minute in the checkout line.

Don’t worry. I fall for it every time too.

Get Your Shoe Style On:

#4. Casual Fridays at Work

It’s 8am on a casual Friday at work. In about 10 hours you’ll definitely be itching to wear Outfit #2. But, in the meantime… it’s time to bust out your best office-appropriate attire.

Jean Jacket Outfit for Office

Trousers (Bershka) | Turtleneck (Amazon) | Denim Jacket (American Eagle) | Loafers (Steve Madden) | Tote (Kate Spade) | Hoops (Mejuri) | Glasses (Amazon)

I love this look because it is insanely comfortable but will also be acceptable for any meetings that may come up during the work day.

The three main pieces of this look can be achieved with regular staples that already exist within your wardrobe. A fun pleated trouser is always in style, and this pair from Bershka is delicate yet sleek. Who says we always have to wear neutrals in the office?

If you’re unsure about how much wear you’ll get out of a bright pair of pants like these (and how much you really want to spend on them), check out your local thrift! Some of my most treasured work trousers were discovered at second hand stores. Pink, sage green, burgundy… I even have a metallic blue pair that I snagged for $8. (Those only come out when I need a serious boost of workday confidence.)

The turtleneck and jean jacket combo is also a reliable choice for casual Fridays. This denim jacket is still button-up, so it’s basically like you’re wearing a dress shirt. Right?

Since the outfit is so versatile based on the jean jacket’s adaptability, go crazy with accessories. Here, I’ve paired the basics with a large houndstooth tote, a pair of platform loafers, some round-framed glasses, and a pair of chunky gold hoops. Keep in mind: this template can be adjusted based on the color schemes that already exist in your closet! Have fun with it, and survive the workday. You’ll get to throw on Outfit #2 in no time.


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Why we should all own a jean jacket

I firmly believe in taking the time to invest in a few durable jean jackets. Why? Because there are just so many ways to style them, as demonstrated above.

Jean jackets have no “season”; and they have withstood decades of evolving fashion and style trends. I think there’s something beautiful in being stressed while getting dressed and walking into your closet only to find your tried-and-true.

For me, that’s an oversized denim jacket. It just… works. With everything. From day to night, denim jackets can be used to showcase your style, your beauty, and your charisma. Reimagine your outfits for these four occasions (and more), and happy styling!

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Madison Gile
Madison Gile is a young professional living in the United States with a passion for all things fashion, trends, and sustainable style. She works in the legal field, but has a lifelong love of fashion and writing. Throughout her college career, she ventured to understand how to influence her peers to view fashion in a different way, one that promotes inclusivity and social responsibility. Madison loves all things vintage; specifically vintage Chanel and Prada. As a 90’s baby and someone who is deeply appreciative of the aesthetic, Madison upcycles 90’s pieces from thrift stores and incorporates the edgy and adventurous style into her intriguing makeup looks.