The DIY Playbook Style Series – Leather Jackets

The DIY Playbook Style Series: Like many of you, we both strive to buy clothing that not only reflects our style, but is also comfortable, affordable, and can be worn at work AND on the weekends (did we mention we don’t want to spend a ton of money either). We know that a lot of the DIY Playbook’s readers are currently in this same exact situation, so hopefully together we can start this new journey of connecting one another with clothes (and sales!!) that make us all feel confident and comfortable. Don’t get us wrong, we are NOT fashion experts and we are not even fashion forward, just regular girls trying to have a little fun with our styles all without breaking the bank.

Fall fashion outfit with black leather jacket, heather grey shirt, brown handbag and distressed jeans. And today we are diving into the details of our leather jacketsBridget wearing a black leather jacket, distressed jeans and sneakers for a casual fall look. A black leather jacket looks great for casual dining.

Because we both recently invested in new leather jackets, we figured this would be a good starting point. So let’s dive into this fall fashion staple.Casey and Courtney wearing black leather jackets in Carmel.

We’re both big fans of leather jackets, as it’s the perfect addition to our wardrobes for those brisk fall days. As Chicagoans, we’re all about making the most out of our time outside before winter comes into town. Because once those chilly temps come, we’re big homebodies who stay indoors and become vitamin D deficient!

Usually we don’t spend too much money when it comes to our clothes, but since this is a wardrobe staple that will be worn over and over…we were okay spending a tad more for leather jackets (like $100-ish). Whenever either of us purchase new staple items we both tend to do lots of research before we swipe that credit card. Shopping for these jackets was no different. We read reviews, checked out lots of sites, and found some awesome contenders.

Our Favorite Leather Jackets for Fall

A collection of our favorite black leather jackets for different looks.

*Affiliate Links Used 1. Double Peplum // 2. Classic Moto // 3. Drape Front //
4. Drape Front with Zipper (Casey’s) // 5. Draped Moto Jacket // 6. Easy Rider //
7. Leather Biker (currently on sale…33% off!!)  // 8. Cropped Moto (Bridget’s) // 9. Faux Suede

Here are the ones we each purchased for our own wardrobes.

Bridget’s Leather JacketBridget in Carmel wearing a black leather moto jacket.

I have actually been looking for a tailored leather jacket for A WHILE! I spotted this one online recently and sent the link to my little sister for her approval (she’s my fashion conscience). Ironically, she emailed me back saying… “that’s the EXACT jacket that I have!”. I’ve borrowed hers a lot over the years so I knew I loved the fit and went ahead and bought it immediately. It cost around $100, which is usually far more than I would ever spend on one piece of clothing but since I plan on wearing this for years (yes, years!) to come…. I didn’t mind spending the extra money.

Fit tips: I bought an XS and it fits extremely snug (however, I’m not always an XS). The faux leather is super soft and very nice quality. And I usually don’t like things to feel snug, but I like when jackets fit more tailored and less baggy…. especially a leather jacket. But since it is a bit snug,  I can only wear very light things under it. If you’re looking to wear layers under your jacket, I would definitely suggest sizing up on this one.

Casey’s Leather Jacket

Casey in jeans and black leather moto jacket with wide lapels. At just over $100, there was no way I couldn’t say no to this jacket. I loooove the “drapey” look, as I think it’s so flattering and instantly adds a little edge to your outfit. My big pet peeve with leather jackets is when they feel so tight like you can barely move your arms. No bueno. This one has stretchy material on the back of the arms, so you have lots of mobility. I’ve only had this jacket for about a month, but I’ve been wearing it constantly. All in all…a great purchase!

What we wear our jackets with

  • Jeans (just got these distressed ones this season. So soft!)
  • White Pants
  • Flannel around the waist
  • Fall Dress (just purchased this dress in navy. Comfortable & soooo flattering. Can’t wait to take pics for you guys)
  • T-shirt or Blouses
  • Pretty much anything!!

Where NOT to Wear your Leather Jacket

A leather jacket isn't the best choice for the beach but it was a beautiful day.And we’ll leave you with this parting advice. A leather jacket may not be the most practical clothing option when you visit the beach. We were not expecting such brisk temperatures during our recent trip to Carmel-by-the-Sea and our leather jackets were the warmest clothing options we brought. So therefore we had to both wear leather jackets down to explore the beach! Talk about awkward. You can only imagine some of the looks we were getting…. and rightfully so! Wearing a leather jacket while exploring the beautiful beach of Carmel.

A collection of our favorite black leather moto jackets.


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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