Styling Leather Jackets Is Hard - How’d I Do?

This video is sponsored by The Jacket Maker.

As someone who’s been into menswear and men’s style very publicly for over a decade now, you might think that I’ve got the whole “how to dress” and “what to wear with fill in the blank” thing down. In some cases, I’d say that’s true — give me a suit or sport coat and I can put some decent outfits together pretty quickly.

But in other areas, especially more casual styles of dressing, it often doesn’t come that easy. And the place where I feel like I typically struggle the most is when it comes to styling leather jackets.

I’ve often wondered why that is. We’re going to explore that question and I’m going to show you how I’m styling five different leather jackets this winter.

**FEATURED LEATHER JACKETS**

**FEATURED LEATHER SHOES**

Join the community as an insider:

Shop essential menswear:

Browse the essential men’s style library:
---
NEW VIEWER? START HERE

---

WHO AM I? GET TO KNOW ME BETTER:
5 Things I Regret Buying The Most

Reacting To Your Assumptions About Me

5 Things I Wish I Knew In My 20s

---

CONNECT WITH ME

Contains affiliate links // Stay tailored!

0:00 - Introduction
0:50 - Why Is It Hard To Style A Leather Jacket?
2:10 - About The Jacket Maker
3:53 - The 5 Leather Jackets
5:06 - Look 1: Suede Shearling
5:51 - Look 2: Brown G-1 Bomber
6:22 - Look 3: Black G-1 Bomber
7:01 - Look 4: Varsity Jacket
7:32 - Look 5: Quiet Luxury
8:05 - Look 6: Suede Biker
8:42 - How Did I Do?

#howtostyle #leatherjackets #winteroutfits

[kaushalpatel]

As someone associated with leather industry, I feel that a Suede jacket (bomber collar or shirt collar) made from goat skin in dark brown or tobacco color is just an awesome piece of apparel to have in a gentleman's wardrobe.

[amandalove]

Wouldn't recommend varsity jackets for older gentlemen. Seems off to me but of course, wear what makes you feel comfortable and confident.

[aPixelcoffee]

Smooth lookbook. Not too convinced of the Jacket Maker, though. I do like the charcoal suede bomber. But poly lining is a no-go. There are some brands and mills that offer technical fabrics (Olmetex) on a high level. With the Jacket Maker, there's zero transparency about the type of poly, unfortunately.

The varsity jacket, albeit a great style, comes in a poly "wool" that already seems to pick up lint like crazy (4:42 + 7:18). Not something I would expect on your channel, which (to me) represents quality *and* appearance in an inextricable liaison. 285$ for a synthetic jacket with some leather seems like a biiit of a stretch in that fashion.

This is just to say: I'm glad you mentioned that they have viscose lining on offer, as well. Maybe next time, present some more of these? They would be more in line with what I've come to expect as a long-time viewer. Just a constructive critique.

Happy holidays — can't wait to wear a Brian inspired New Year's outfit soon. 😉

[kallekalis]

7:09
I’m personally in love with varsity jackets in a preppy, Ralph Lauren-esque way. However unfortunately for you and men in your age that’ll probably come off as a bit childish maybe… Throw on a baseball cap and wear the jacket to a game and you’ll be good ✌🏼

[ExploreXplore]

This is a nice casual outfit. The brown jacket looks nice and causal. Not sure about the jeans as it's a light colour and it seems like you are wearing a winter outfit. So I would got with dark wash jeans or even black. The shoes go's nicely with the jacket.

[inigosuarez]

As a suggestion: For the Varsity Jacket, you can dress it up too. Like, swap the jeans with chinos/trousers, from turtleneck to polo shirt/button down shirt with/without tie. from white sneakers to boots. This will create a "preppy" look.

[tastybrownie]

OCBD (Oxford Collared Button Down?). What are the best brands of OCBDs?

[plappin]

I don't care for any of these and it has nothing to do with your styling. For my eye, the stark contrast between the leather and the shearling collar is too dramatic and somehow manages to make the jackets look cheap. The varsity jacket looks too much like one is trying to dress like a college student; doesn't make sense for a middle-aged man. I think a blouson-style soft suede jacket with maybe a nehru-type collar -- think 70's YSL -- is a sophisticated style that would work for you, Brian, and would allow for more interesting layering. These jackets are all too blah and boxy in their cuts and again, to my eye, look unsophisticated.

[raymondgallacher-hv]

This is, I believe, the first ever comment I have made on Youtube. I enjoy your videos immensely. Thanks for dressing us all up a little better. The outlets you mention aren't available where I live but the matching advice is universal. Please continue. I note you were a bandsman. Did you ever play at the Edinburgh Tattoo?

[glo_me]

Great to see you are back on YouTube with some amazing content; I was already missing the great outfits and vast knowledge.

Hope you and your family had an amazing Christmas.

By the way, when will the Monarch Butterfly Black Bow Ties be back on the He Spoke S shop? I have kept eyeing them for any re-stocking but nothing thus far.

Wishing you nothing but the best! 😊

[EscobarStyle]

I also have that problem where I’m not that age of a rock and roller. I’m almost 45 now and with these few amazing leather jackets I have, I BARELY wear them and I love them! And what’s sad is that they have been sitting in my closet for quite sometime.

[antoniouloukas]

There is a reason you cant really make leather jackets to work for you and its simply because they require a style that doesnt work for you. Leather jackets are not suppose to be leveled up, feel luxurious and grown up. They are a piece of equipment. Its supposed to be rough and tough and edgy. You can have a more tammed down leather jacket in the form of cafe racer style, or trucker type and maybe swap leather for sued(which is a downgrade to me, i dont why people call it more luxurious, i guess its gives out a softer and warmer feeling). But it would still have be a casual look. They would pair better with a thick casual wool sweater at best, western or worker shirts and dark denim or canvas trousers and off course leather boots.

[JOHN_F_KENNEDY_DADDY]

What do hot girls say about your outfits

[FredLock]

This video comes at the perfect time for me because I've been strongly considering buying a leather jacket. Mostly because I just think they look cool. But I also wonder what else, besides the obvious, I could wear with one. Thanks for the suggestions!

[WesleyPeters-dl]

hey brian, nice video. Please make more videos like this

[Vikiify]

I spot a Lange 1...can we expect a watch review of this amazing timepiece?

[tmack-rxih]

Toss up between looks 5 and 3 as my favorite. Looking for a way to incorporate a pair of white jeans into the winter rotation.

[faridmahnad]

Christmas has come . . . a little late??? Welcome back!!
That black/brown outfits rocks.🎉🎉

[gregzargo]

Jacket Maker seriously sucks when it comes to buying stuff. They flood their reviews with fake ones and delete anything negative. It's like they have zero ethics. Plus, their customer service is a joke - totally unprofessional. That's why I had to hit the unsubscribe button on your channel, especially since you're cozying up to Jacket Maker with sponsorships.

[dinomite]

When are you coming back to Youtube Brian? Missing the regularly scheduled programming on the channel. Great content as always. PS any Italy-trip videos coming up?