Fall Fashion Suggestions

Since probably about my senior year of high school, I’ve taken an interest in fashion.  I love clothes, accessories, shoes, brands, designers, stores, etc.  Everything about men’s fashion is intriguing to me.  I once heard sort of a cheesy quote, and it’s stuck with me:  “A well-dressed man is to a woman what a scantily clad woman is to a man”  Men today are dressing better than they have in decades, and that’s part of this growing acceptance of men being comfortable in their own skin.  I refuse to use terms like “metrosexual” or claim a man is in touch with his “feminine side.”  I hate that.  Those terms imply that taking pride in your appearance is a womanly attribute, and that’s offensive to both genders, in my humble opinion.

My high school did not have a particularly well-dressed student body.  Everyone pretty much always either dressed in faded blue jeans and a t-shirt or gym shorts and a hoodie to school each day.  Sneakers went with everything, and I remember people actually wearing jeans to the Homecoming dance.  This isn’t to suggest those students weren’t fashionable people, because I knew some kids who could make gym shorts work.  I just think it’s part of a small town culture, where everyone is just comfortable with the basics.

When I started college, things changed.  Don’t get me wrong, by mid-freshman year half of the student population was wearing sweatpants to class every single day, but the students who tried to look their best always inspired me.  For the first time, I saw guys experimenting with tighter, slimmer jackets and jeans, colorful shirts with stripes and patterns, and they always had some sort of product in their hair.  It was inspiring to see these guys do their best to look their best.  Honestly, I lauded how bold these guys were.  At my high school, dressing like that would get you picked or called derogatory names.  And here I was, 20 miles away, watching the aura of confidence emanating from these dudes.

Once I moved to the city, I was exposed to even more fashionable men.  All over downtown Pittsburgh were these guys who had it figured out.  Men headed to work in perfectly tailored suits, with the perfect watch, perfect bag, and perfect hair.  Younger guys in college looking sharp as possible on a college student budget.  That’s what’s great about fashion:  The amount of money you spend is irrelevant.  Owning a look, regardless of price tag, can make you look like a million bucks.


The handsome guy on the left is my brother, Jay.  The equally handsome guy to this right is Mike, who I’ve mentioned on here previously.  As you notice, they both look sharp.  Jay is going with a pair of medium wash jeans with light fading, as well as a light blue, cotton seersucker jacket on top of a solid white Oxford.  Completing his look, although not pictured, is a watch with a brown leather band.  Mike is going with a pair of dark blue khakis, the light tan belt to match his light tan wingtips (not pictured), and a crisp, light pink Oxford with the sleeves cuffed.  Their haircuts are impeccable, both guys using pomade to shine and style their hair, both of which went with a side part; a classic, timeless look.  They both look great in these clothes, owned these looks entirely, and I can tell you with confidence the most expensive item on their bodies are the pair of Ray-Bans each man is wearing.

The attire selected by Jay and Mike, coincidently, are great fall looks.  Jay’s cotton jacket can keep him warm on the more crisp fall days, but it’s light enough where he’s not uncomfortably warm by around 3 p.m.  Mike, on the other hand, went with a more dressed down, but classic fall look, that looks as good in an office setting as it does out at the bar.  Mike can easily layer on a nice, light jacket and be ready for the weather.

Here are some other items I consider essential for fall:

Desert boots by Clarks – These are the perfect fall accessory, and I can’t recommend them enough.  Not only are they 100% leather, so they get more comfortable over time as they mold to your feet, but they are as durable a shoe as you are likely to find for the price ($110 clarksusa.com)  Pair with jeans for a casual look, or team them up with khakis to dress them up a bit.

Fabric Strap Watches – Fall is a time for walks outside amongst the beautiful, aesthetic scenery.  Most fall looks hinge on the casual side to match this outdoorsy feel, so the simple white face goes perfectly with a nylon or fabric strap that isn’t too formal.  The best part?  This watch will only run you around $30 (timex.com).

Cotton Jackets – As much as I love the ever trusty and stylish wool pea coat, fall calls for a lighter variety of outerwear.  Cotton jackets are a simple way to give a bold, rugged edge to your fall look, while still staying stylish.  You can layer them up without worrying too much about the later day heat becoming an issue.  Tip:  check the clearance or sale section first.  Retailers are quick to sell last year’s styles, even though there is rarely any discernible difference.  The jacket above is from H&M, a very wallet-friendly store that doesn’t force you to compromise your style.  It goes for a cool $99 (H&M.com).

Jeans – It feels a little ridiculous to pitch a pair of blue jeans, seeing as they are the most common form of clothing in the world (except Russia, where track suits are on top for the 60th year running).  However, I see a lot of people doing jeans wrong.  What you want is slim-straight fit, a perfect balance between straight leg and skinny.  Slim-straight jeans and pants are flattering for all body types, and can actually make heavier men look trimmer.  If you own any relaxed or bootcut jeans and you aren’t either A) a farmer or B) a member of NWA, it’s time to move on to something better.  Another rule of thumb:  the darker the better.  I personally try to always go for a medium-dark wash, with minimal to light fading in the legs.  The 121 Heritage Slim (luckybrand.com) from Lucky Jeans are the perfect pair.  Made from supersoft denim, these jeans are like putting on a pair of fleece sweatpants, and they are built to last.  And a $99 price is reasonable for the longevity of this product.  Pro-tip:  Don’t wash jeans after every wear.  In fact, you can wear jeans for a while before they need a wash, maybe as long as a week or so.  Frequent washings break down the fibers of the denim and also fade the jeans.  Not good for a dark pair.  If you find them getting stinky in between washes, spritz lightly with water and white vinegar and hang to dry.  This will kill the odor.

General Tips:

  • try to always wear a watch.  It adds depth and maturity to your look.  It also allows you to not always need to dig out your phone when you need to check the time
  • Other accessories to consider include wool knit ties, slouch beanies, wayfarer or aviator sunglasses, wool socks, and Henley shirts
  • Cuff your jeans to add a subtle flair to your outfit and NEVER mismatch your belt and shoes.  A black belt with brown shoes should be considered an act of war under the Geneva Convention
  • Fall=rugged, so if you can rock some stubble on your face, do that.  If you can grow a full beard, go total mountain man with it and own the wilderness.  But no matter how rugged you appear, never be afraid to order pumpkin spice in your coffee.

Fashion is an entirely subjective area of interest, and that’s part of why I love it.  Some of you reading this probably think some of my thoughts regarding what looks nice are ridiculous and stupid, in which case you are, of course, 100% entitled to that opinion.  I just hope my taste is good enough to maybe influence some people to branch out in their own styles.  If you take nothing else from this article, I implore you to at least take my advice about sticking to darker jeans.  The days of this,

must come to a swift, and violent end.  Oh, the horror.


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