Styling a Leather Jacket With a Hoodie

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Few looks are as iconic and quintessentially American as leather jackets. Leather has been in style continuously in America for decades. Just think of how often it shows up in pop culture. Whether it's James Dean in Rebel Without A Cause, Marlon Brando in The Wild One, or Wesley Snipes in Passenger 57, leather jackets have been a cornerstone of American men's style for years. These days, one of the most fashion-forward ways to wear a leather jacket is with a hoodie. When styled right, this is a versatile look that straddles the line between casual and effortful dressing.

How to Choose a Leather Jacket

Leather jackets are available in a variety of colors, grains and cuts. The leather jacket you choose should match your vibe and your look. Your comfort is always important in how good you look, whatever the outfit is. In general, quality leather should feel rich to the touch. If you're looking for something rugged, like a protective biker jacket, choose a thicker hide. Lighter-weight hides are sometimes in fashion, but they harder to layer and won't provide as much protection from the elements.

In general, people in the know describe the best leathers' texture as soapy. Popular cuts for leather jackets include biker, bomber, moto and field coats. Currently, long leather coats, especially trenches, are seen as dated and should be avoided. They conjure up images of 90s working stiffs, especially security guards and investigators. Of course, the most important accessory to pair with any garment is confidence. If it's you, go with it. Be your own shot-caller.

Pairing a Leather Jacket With the Right Hoodie

One of the most fashion forward ways for men to wear their leather jackets now is to pair them with hoodies. It's tres au courant, as they say in Paris. The great thing about this look is that it's both casual and sophisticated. There's a reason it's fast becoming the urban hipster uniform. Wearing a hoodie under your leather jacket suggests a certain rugged urban pragmatism. People who favor this practical, easy look often work in tech or in the arts. It's a very youthful trend. That said, whether you're 20 or 50, this pairing can absolutely be a part of your regular rotation.

Of course, two thick layers can be a lot of look. And you do want the hoodie to be thick. So, take care as you choose both the jacket and the hoodie. This is an easy look to get right. When it's done wrong, though, it can look lumpy and downscale. You want to look like you stepped from the pages of GQ or Sports Illustrated. You don't want to look like a henchman in a Steven Seagal movie. For this fashion statement to really work, the jacket shouldn't be too narrow and fitted. You want a classic leather jacket with some body to it.

The hoodie you choose should also have a decently thick, full feel. You want a classic hoodie, not something lightweight, for this look. Retailers like The Idle Man make good basics that work well with this look. Available in heathered grey and basic neutrals, their best sweatshirt options include vintage-inspired Champion crewnecks. Suitable hoodies are available in both zippered and pull-over versions. Good options come from brands like T.I.M. Preppy versions with Gap and J Crew sweatshirts can work, too.

Crafting Your Pairing

Completing the look is fairly easy. Start with a tee. Layer with a hoodie. Apply your favorite leather jacket over the top. When it comes to pairing a hoodie with a leather jacket, in general neutrals will be your best friend. When I lived in NYC, one of my best friends (Jared) favored a bright yellow hoodie. He wore it daily. As nice as he is, it's a terrible look. So don't be a Jared when it comes to this.

Heather grey is a great choice with black leather. Or brown, really. The contrast between the light and dark colors is really striking. It ramps up the visual interest. Blues and darker greys are also solid choices. For brown bomber jackets, greens, especially muted or forest greens, can really be effective. But to be honest, I prefer a medium grey with a brown leather jacket.

The general look is to wear the jacket open with the hoodie visible underneath. The hood should always be popped out to show over the back of the collar. Of course, New York and New England's fashion-forward men sometimes legitimately need to close the jacket and put the hood up, too. That pragmatism is a great benefit of this look. It's truly effective, both style-wise and for warmth. Remember, thicker, biker-style leather jackets will also be highly effective at repelling rain and snow. Jackets from retailers like LL Bean are also known for being sturdy. If the leather's properly treated, water will bead on it.

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Keeping the Look Under Budget

This is a look that really be put together at any price point. Of course, the lower you go in price, the lower-quality the leather jackets that will be available to you. Consider going vintage if cost is a real concern when it comes to finding the right jacket. Estate sales, consignment stores, costume shops and thrift stores are all good sources for great deals on leather. Don't neglect online sources, either. Retail sites like Poshmark are a great source for deals on high quality basics like leather jackets.

Even if you go pre-owned or vintage, make sure to look for signs of high quality. Be aware that good quality leather is typically cut and stitched along similar patterns to woven fabrics. Leather jackets that use extra seams are generally not just making a fashion statement. No one hacks up great quality hides like that. This is typically a strategy to save money and get the most volume from a hide. These jackets use lots of odd bits that would typically be left on the floor. Looking for minimal seaming is a trick that can help you spot quality leathers from across the room. This can be a great time saver when you're shopping.

Frequently Asked Questions

Where can this look be worn?

This is an extremely versatile look that can be worn almost everywhere. You can take it to many workplaces, depending on your industry. It's a great look for any grad student or young professor. The hoodie with a leather jacket is fast becoming this generation's blazer with elbow patches.

What, exactly, makes it so versatile?

The key to this look is really that it's a version of mixing high and low style. Sweatshirts are usually made of cotton or poly-cotton knits. These are comfortable and easy to care for, but they can look over-casual and inexpensive. Adding a leather jacket, which is more expensive and more structured, takes the look up a few notches.

What is the key to this look's appeal?

Hoodies suggest youthfulness and athleticism. What do you see when you look at a guy in a hoodie? For most, it connotes someone who has an active life and possibly a physical job. Leather jackets, too, suggest an active and accomplished lifestyle. Our classic cut jackets all derive from active, vital activities like motorcycle racing, flying vintage aircraft, working on a ranch. What this look is really saying is that you're vital, active and really get things done.

Pros and Cons

 Pros

  • This is a versatile look that, for many workers, can travel from work to happy hour.

  • Pairing a hoodie and a leather jacket is an easy look. It can be worn by just about anyone.

  • This look is youthful and easy to put together. If you have quality basics you can wear it forever.

Cons

  • This look combines two garments that are each American icons.

  • Done wrong, this look can make you look like a bad 80s bouncer. Make sure your outfit drapes well and doesn't have weird lumps and bulges.

As versatile as this look is, it doesn't quite rise to the level of business casual. If your industry is more formal, save this for casual Fridays.

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Putting it All Together

Pairing your leather jacket with a hoodie is one of the biggest trends for winter 2019. It's arguably an ensemble that's becoming a new classic. All the fashionable men are wearing it, from actors and musicians to everyday Joes in the trades. That's one great thing about this look: it's completely democratic. You can wear it on the farm or in the big city. This pairing works amazingly well for any size, income level or age. That's what makes it uniquely democratic, and of today's woke moment. How are you planning to wear it? Where will you take it? Do you like our tips, or did we fall short somewhere? Let's chat about it in the comments below.

GuideMaria Ermolenkostyle