Trendy Layering: Hoodies with Leather Jackets

We’re going to jump right into the thicket with this one. A few weekends ago, I went photoshooting with my first photographer, Mayur (also my neighbor in case you weren’t wondering), who has a FB page with his photography you can access here

I recommend you go through this article on a tablet or computer because it has a significant amount of pictures which may take time to load on your phone and/or eat up your data if you’re not on WiFi. Optimal Outfits is also optimized to be viewed on your web browser so for the full experience, I definitely hope you’re going through this on the big(gish) screen. 

If the guy on left is the photographer, then who took this picture? 

Today I wore an all-black outfit; those of you who know me instantly know this means it is one of my favorite, most-worn, color combinations. I love all-black because of the simplicity and trendiness. The way I view the world, we’ve got maybe 80 years “guaranteed” on here, and for the last 50 of it, we’re forced into wearing old-people clothes. 

You could consider this my last gasp of teenage rebellion before I hit 20 and have to start falling in line with the rest of the adults.

Unknown/H&M/Rogue Territory/Converse

The brands of this outfit each have a distinct connotation which come together nicely to create a mix of trend and timeless. My leather jacket, which I bought second hand, is probably the most “out-there” piece of the outfit. I’ve worn this once before and written about it here when I layered it with a turtleneck sweater and the same black denim. Leather jackets come in numerous styles (guadyflight jackets to name just two), the most recognizable – if not most classic – being the double rider shown here. 

Every black & white badass (iconically Marlon Brando and Steve McQueen) had a double rider in their rotation. This hasn’t changed since life moved to color in the 1960s; now we just see our icons as former football players and boyband members. It just goes to show how some styles never change; why investing in a jacket that you can be buried in is never a bad idea. 

Two thumbs up for the recommendation

As far as double riders (and leather jackets as a whole) go, mine is extremely minimalistic which allows it to fit perfectly with my preferred aesthetic. There are two side pockets, a diagonal zipper, and uneven lapels characteristic of a jacket meant to be worn while riding a bike. The only design “flourish” present on the jacket are the epaulets on either shoulder. 

At this point, if you have a brain you might be wondering how much money this jacket cost. Admittedly, it cost a decent amount of money, I can’t deny it; however, I can say that because I bought it secondhand, I managed to save myself nearly $500 than if I had tried to buy a jacket of this quality new.

Buying clothes secondhand is definitely a tip I recommend to anyone looking to get into higher end fashion but finds the sticker-shock still present. 

If you could ask the people who sit around me before lecture starts, you can definitely find out how much time I spend on Grailed (think Ebay, but just for men’s clothes) looking at pieces. Grailed is what allowed me to find this amazing jacket for easily 1/3 it’s true cost, my favorite burgundy sweater from APC’s F/W 2015 collection for less than $90 (originally would have sold for around $300), and my light-wash Acne jeans (which I also policed for sub $100 while they retail for $300+).

It might feel weird at first, wearing other people’s clothes, but trust me, your (parents’) wallet will love it*. 

Grailed is neat because it’s specialized in only catering to buyers/sellers of male fashion. Because this is still a relatively small niche, the quality of items for sale are significantly higher than what you might find on Ebay and (in my opinion) the base of sellers are more diverse than what you’d find on other internet buy/sell groups. A quick search on Ebay and local Facebook buy/sell groups either rarely returns more than one or two pieces related to your search query, and then it’s another crapshoot to see if the few pieces available are actually in your size.

*Kidding, I don’t actually use my parents money for this, but it is a convenient joke to make.

Turtleneck ebayFor example, a search for “turtlenecks” on Ebay returns a screen of brands you can find at your local mall. Cheaply woven, horribly modeled garments which cost less than the moral bankruptcy of their producers (see: clothes pinned back around the mannequin to hide a poor fit in second from left, bottom row).

turtleneck grailed.jpeg

On the other hand, the same search on Grailed returns much more diverse results from designers with history behind their name in a variety of colors, fits, and styles. Right about now is when the stick shock should hit (see: $10,000 Raf in bottom right), so I’ll go ahead and say I did not constrain the search with a price ceiling. At the very least, the Burberry on second from right on the top row should be an indicator of how affordable designer fashion can become when purchasing second hand.

In any leather goods, the most important aspect is the grain of the leather: full grain is the best option (if you can afford it). 

Full grain comes from the uppermost layer of the animal’s hide and retains all of the animal’s grain. For the designer, this is relatively more difficult to shape into their vision compared to top or genuine leather, but rewards them with a near-flawless construction once completed. Hence, full grain leather costs significantly more than top grain; the latter has the uppermost region removed and instead uses the hide underneath the area where full grain leather originates. This allows for a looser grain which makes constructing the jacket easier, but also means it will break down faster than a full grain jacket. 

Additionally, full grain jackets develop a “patina” over multiple years of use which is impossible with top or genuine leather jackets. It’s a similar concept to “fades” on raw denim except with leather. Essentially, the leather develops a completely natural “shine” which is impossible to reproduce on non-full grain leather because of the uniqueness of each animal’s hide. The combination of moving with your body, sun/environment exposure, and natural wear combine to form a beautiful “discoloration” of the leather. Below you can see two identical wallets, one newly made and another from a few years of use to see what patina looks like.


If this blog sticks around into the 2020s, I hope to show that off to you guys. 





Instead of a sweater, I layered a black hoodie from H&M underneath to continue the monochrome. The hoodie adds casualness to the outfit and would allow for an easy transition from the trendiness present with the jacket on, to a more relaxed, “college-y” vibe with it off. 

A couple months ago, I promised an article on how to wear every college kid’s favorite article of clothing and this is my recommendation: layer your hoodies underneath your jackets. 

Not only does it look unique, but the jacket (leather, bomber, or even wool coat) + hoodie combination has been a trend since late winter 2015 at least. I’d recommend on focusing on hoodies that have a simple, unassuming design. Solid, neutral colors (navy/grey/black) are the safest bets and zipperless is generally better for when showing off the layers (although on its own I’d preferred zippered front over non-zippered). 

I love this outfit because it features a $20 hoodie with $200 jacket

I’ve had this hoodie since spring 2015 and somehow it hasn’t fallen apart yet. HM is notorious for low quality clothing sold at stupidly-low prices, but somehow this hoodie made it to the finish line while numerous other pieces I’ve bought since then have fallen apart. Keep that in mind when purchasing clothes from them. They’re great for experimenting with a new trend and for dipping your feet into the fashion world, but at some point you’ll want to move on and buy higher quality which will last longer.


If you’re looking for a throwback, check out my first post on Optimal Outfits from September 2016 which features the same jeans worn for the first time. I said back then that if we give it a few years and we’ll see some “sick fades” on these raw denim. It’s been two-and-a-half years since I first bought these jeans, I’ve worn them over three hundred times, and washed them at least two dozen times since then. I’m proud to say, I think I have “sick fades” on my favorite pair of pants. 




They definitely have lost their “blacker than night” look when I first copped them in August 2015 and it only took 27 months! In similarly exciting news, this now means I will be re-entering the market for black jeans and would love to hear your suggestions! 

If this isn’t a shoe advert, I don’t know what is

The shoes are my second favorite part of this outfit. I love my Converse and they are my most worn shoes in my rotation. Now that I have retired my Stan Smiths, these have become my most versatile and ubiquitous shoe. I love wearing them with my black denim as shown here, but am equally likely to slip them under a pair of navy/grey chinos. Wearing these with indigo jeans isn’t my preferred or favorite look, but I’ve seen lots of people around campus combine the two, so I’ve been trying to do the same. Nobody has commented that it looks ugly (yet), so I might be overreaching by not wearing the combo more often, but I prefer being cautious at times.

At this point, I’d like to share a little bit of history about Converse. They are the most American shoe in existence. Children across the globe from every generation since Milton Converse began athletic shoe production in 1915 have worn these kicks. Nobody has confirmed it, but it is believed that a pair of red Chuck Taylors were the first item to cross the Iron Curtain once the Berlin Wall came down. 

I have the new Chuck II’s with Nike’s Lunarlon sole on the bottom instead of whatever wooden planks the old version use and I cannot recommend a better shoe for the typical college kid than this. Nike’s magic turned out a shoe that is built for walking miles around campus without any pain across your feet. I prefer mine in black with black lace as they blend into my black jeans, but red was definitely my second choice (which I might one day still snag once I have enough money for a credit card I use only on clothes). 


Definitely keep them untied, you’re not some nerdy loser

I love the look of beaten-up sneakers and nothing’s better than Converse for that purpose. For me, they age like Jennifer Aniston and thus despite never cleaning them, the dirt and tears only add to their trendy, urban appeal. At the very least, they make me look like I actually go to moderately-exciting activities in my life so I don’t mind. 


My photographer says I need to talk about the pop of white from the tee shirt underneath which contrasts my black outfit. Really he just wants an excuse to ensure I included the featured picture in this post (which is prime as hell, so I was always going to include it) but I don’t think anyone actually reads this far into my posts (including him!) to see this. In case you did, let me know via comment/text/SnapChat/postcard and I’ll let you select a reasonable theme for my first “themed” outfit post. 

This is the closest StL will ever get to having an iconic scene

At this point, I’ve covered everything I wanted to say and will be signing off soon. As usual, below you’ll find the extras from the photoshoot which didn’t make it into the main body but were too good to not include. I’d like to thank my photographer, Mayur (who has a bio on our About Us page) for these kickass snapshots and the city of St. Louis for having a 60 degree day within 72 hours of a below-freezing school day. This photoshoot and outfit could not have happened without you guys. 

Thanks for reading,


Getting the leaves to fall in frame was harder than waking up at 8 on weekend mornings
You aren’t supposed to zip up your jacket because “it’s not cool” but sometimes you need to know when to break the rules

Everywhere I go, they [trichomes] are always calling my name

Get on our level
Ever since I became obsessed with myself, I’ve always wanted to make it on the big screen. Today, my 2 year old dream just became reality.



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