Leather Jacket Outfit Ideas From Casual to Dressy

I’m showcasing 5 leather jacket outfit ideas that include outfits for a casual day and even dressy occasions. It’s always a challenge for me to figure out how to make my pieces versatile. And what better way than dress up or down a piece along with showing it with different colors.

Is it Too Matchy to Wear the Blue Jacket with Blue Jeans?

I figure most casual outfits start with blue jeans. Sure, my jacket matches my jeans somewhat, but then it almost looks less casual. Maybe?

The weather had been chilly for a couple of days, so I took advantage by wearing a hat and boots along with my Peach velvet sweatshirt.

A Day of Shopping

This is my outfit for our trip to Phoenix for Small Business Saturday shopping. The weather was still chilly, and my hair was still a mess. So I donned this fur thing on top of my head that I had picked up at another small business, The Pink House Boutique, the day before. It reminds me of a Russian lady and I can wear it around my neck like a scarf too.

For this day, I wanted to lighten up the look so I put on my Chicos, No Stain white jeans. The sweatshirt makes me feel 10 years old and that’s a good thing. I’ve worn it on the blog before and I was worried I wouldn’t be able to wear it much out here in AZ.

Can You Wear Leather and Leather?

For this outfit, I wanted to experiment with a different colorway with the blue jacket. When I grabbed this snakeskin leather skirt, it made me think if leather and leather were okay together. And then I decided of course it's okay. The skirt was a great find on thredUp which is an online thrifting site.

This goes to show I do wear black occasionally. Of course, I had to add in color with the scarf and beret. The scarf wouldn’t stay in place well, so I tacked it down with a brooch. Those accessories come in handy for more than just decoration.

Isn’t a Leather Jacket too Casual for Dress Up?

No. Never. Not on your life. Get the picture? Part of today’s modern look is adding in dichotomy to your outfits. Maybe not for every occasion and event, but certainly many of them.

So wearing this blue leather jacket with my velvet dress was a fun way to style this concept. This dress is one of the items from my Fashom box that I was enamored with recently. And if you’re wondering. That purse? It’s actually a wine carrier. It’s a wonderful thrifted find.

Make sure to see the last way I wore this leather jacket on the blog.


I was gifted this jacket from The Jacket Maker. In my experience, I have learned to ask what is expected of me for the rare gifted products I do accept. They only asked for me to share my thoughts in an Instagram post which I did here.

Yet, this company is quite impressive and I don’t know how they do it. Their jackets are custom-made to your measurements. And yet their prices are the same as the leather jacket I splurged on a couple of years ago (and maybe less). That’s why I didn’t realize that this jacket was made just for my measurements until I received it.

This is a real leather jacket. I could smell the leather when I took it out of the packaging. And the best part was how well it fit. The sleeves weren’t too long (which is the case on many of my jackets). And the shoulder seams and length were just perfect.

If you asked me the cons about this site, I would say two things.

1– Most of the jackets are dark, and you know how I like color. While I picked this blue one, it’s really a cool blue instead of warm blue.

2– The packaging is quite generic. Then again, maybe that’s one way to keep their costs down.

Insider tip: Since this is made for your measurements, you have to realize that there isn’t a lot of extra space if you like to zip it up. If you tend to wear bulky items under a jacket like this, you might want to pad the measurements an inch or two.

Addendum: 3 months later and I have still been very impressed with my jacket. So much so that I signed up to be an affiliate for their company. That means I could get a commission if you purchase from them. As a former small business owner, I think it’s important to support these small businesses and I appreciate you supporting me.

The author may collect a small share of sales from the links on this page.

Jodie Filogomo
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