15 Stylish Oversized Jacket Outfits for Every Occasion

Oversized jackets are having a significant moment right now. These comfy pieces make any outfit look effortlessly cool while keeping you warm.

Interestingly, they come in many styles, colors, and fabrics.

From denim to leather, there’s an oversized jacket that fits your personal style.

Related: 14 Stylish & Trendy Cropped Trench Coat Outfits

15 Amazing Ways to Style Your Oversized Jacket

In the section below, I will share 15 oversized jacket outfits I love.

1- Classic Denim Jacket with Skinny Jeans

I love this timeless combination because it never goes out of style.

You can wear a light blue oversized denim jacket with black skinny jeans and white sneakers. This creates a balanced look that’s neither too baggy nor too tight.

2- Oversized Blazer with Mini Dress

This outfit gives you the perfect mix of professional and playful vibes.

You can choose a neutral blazer, like beige or gray, and wear it over a fitted mini dress. The contrast between the loose jacket and fitted dress creates a flattering silhouette.

3- Bomber Jacket with High-Waisted Pants

Bomber jackets are super trendy and super comfortable.

I recommend pairing an oversized bomber with high-waisted trousers or jeans. This creates a nice balance and shows off your waistline even with the loose jacket.

4- Leather Jacket with Flowing Maxi Skirt

This combination might sound unusual, but it creates a fantastic contrast between edgy and feminine.

In my experience, you can wear a black, oversized leather jacket with a flowy midi or maxi skirt in a soft color like cream or dusty pink.

5- Cardigan Jacket with Leggings

Cardigan-style jackets are incredibly cozy and perfect for relaxed days.

You can wear a chunky knit cardigan over a fitted tank top with black leggings. This creates a comfortable yet put-together appearance.

6- Trench Coat with Shorts and Tights

An oversized trench coat can make shorts appropriate for cooler weather. Interestingly, you can wear the trench over denim shorts with black tights or leggings underneath. This creates an interesting mix of seasons and styles.

7- Puffer Jacket with Athleisure Wear

Oversized puffer jackets are practical and trendy at the same time.

I recommend you style them with matching sweatpants or leggings for a coordinated athletic look. This outfit is perfect for gym sessions, casual errands, or comfortable travel days.

8- Wool Coat with Midi Dress

A long, oversized wool coat looks elegant and sophisticated.

The coat adds warmth while the dress maintains femininity underneath. You should choose classic colors like navy, camel, or charcoal for your wool coat.

9- Hoodie Jacket with Biker Shorts

This sporty combination is both comfortable and on-trend.

The contrast between loose and tight pieces is very flattering. This outfit is ideal for gym workouts, casual walks, or running errands around town.

10- Flannel Shirt as Jacket with Tank Top

Oversized flannel shirts make perfect lightweight jackets. You can wear them open over a fitted tank top with your favorite jeans.

This creates a relaxed, effortless look that’s perfect for casual days. I highly recommend you choose flannel shirts in classic patterns like plaid or check in colors that complement your existing wardrobe.

11- Kimono Style Jacket with Wide Leg Pants

Kimono-style jackets offer a flowy, bohemian vibe that’s very comfortable.

You can pair them with wide-leg pants in a coordinating or contrasting color. This creates a relaxed, artistic look that’s still put-together.

12- Varsity Jacket with Pleated Skirt

This combination gives you a fun, youthful vibe that’s reminiscent of school days but much more stylish.

You can wear an oversized varsity jacket with a pleated mini or midi skirt. The sporty jacket contrasts nicely with the feminine skirt.

13- Military Style Jacket with Fitted Jeans

Military or utility jackets have a structured yet comfortable feel.

This creates a practical yet stylish everyday outfit. Choose jackets in classic colors like olive green, khaki, or black. The multiple pockets add both function and visual interest.

14- Shacket with Bike Shorts and Knee Socks

A shacket (a hybrid of shirt and jacket) is perfect for transitional weather.

You can style it with fitted bike shorts and knee-high socks for a trendy, layered look. This combination is both practical and fashionable.

15- Oversized Blazer with Paper Bag Waist Pants

This combination offers sophistication with comfort.

The blazer adds formality while the pants keep things comfortable and trendy. This outfit works perfectly for casual office settings, lunch meetings, or any occasion where you want to look professional yet relaxed.

Conclusion

These outfit ideas are just starting points for your own style adventures.

The beauty of oversized jackets is that they work with so many different pieces in your closet. You can mix and match based on your personal preferences and lifestyle needs.