How to Wear a Classic Denim Jacket

How to Wear a Classic Denim Jacket
Post by Trunk Club
July 3, 2019

What to wear with a denim jacket

There are few things that fit as seamlessly into everyone's wardrobes as the denim jacket. This classic-cool staple is the piece to own when it comes to mixing and matching. Your look could could be inspired by designer labels, urban street style, or James Dean—and a classic denim jacket would fit perfectly in your wardrobe rotation. With that in mind, we're exploring five fresh jean jacket outfits to help you wear this never-going-anywhere men's essential. Talk about versatile.

Denim jacket with plaid shirt and jeans.

Look 1

Keep it classic with a plaid shirt

Does your style lean toward laid-back? Then you should consider this your fall uniform. Start with a base of slim-fit jeans and a jean jacket with a plaid shirt. The jacket can be layered on or off throughout your day. Complete the look with leather or suede to balance all that denim: a pair of Chelsea boots and a simple belt will do the trick. 

Look 2

Elevate your T-shirt and jeans

If this is your go-to combo, you can still give it extra style. Layer a denim jacket over a long-sleeved tee in earth tones, then cuff the jacket sleeves (just once is enough). Regular-cut jeans in a dark wash will make clean white kicks really pop.

Denim jacket with a tshirt and dark jeans.
Denim jacket with a henley and khakis.

Look 3

Refine your rugged style

A denim jacket is perfect for pulling off a rugged look that's cleaned up around the edges. Start with slim-fit chinos in dark moss and a fitted chambray shirt. Experiment with layers by adding a henley on top, leaving the top button undone to give your collar room to breath. A handsome watch and classic work boots are the ideal finishing touches.

Look 4

Hit the street

For a casual look that feels modern, put the emphasis on contrast: a cool pair of joggers with a plain white tee and a black leather shoe with a bright white sole. A leather jacket would be too much, and a parka would be too casual—that’s why a denim jacket is just right.

Denim jacket with grey, plaid joggers.
Denim jacket with sweater and tie.

Look 5

Denim jacket and tie

If your office dress code is business casual, you might be surprised to learn how seamlessly a denim jacket fits into your workwear mix. Go with your standard formula of polished pieces: button-down, V-neck sweater, and chinos paired with a tie and derby shoes. Top off with denim and you’re out the door.

At Trunk Club, our stylists help people build their best wardrobes by discovering what fits their body, their budget, and their personal style.