Advice: Jacket/Jeans

Easy visual reference.  Understood?
Images: FanPop and J.Crew's favorite looks

What better way to return than to dispense some much needed advice to one of my three avid readers.

J/P writes:

Yo R/C

I'm tooling around with the idea of trying out the Jacket/Jean combination. Whether it be a t-shirt or button down under the jacket is unknown. What should I be looking for as a versatile coat that will allow me to pull off either look, not look like a douche, and be affordable?

A hardy "yo" to you my fashionably bewildered chap,

I applaud your forward thinking of the upcoming season and the fortitude to ask for advice when needed. It just so happens that I have many opinions on this subject and you have offered me an excellent chance to rebound from the depths of summer with a much overdue post. I too have been conceptualizing my fall wardrobe and am eagerly awaiting the cooler weather that necessitates a stylish jacket and a pair of jeans, finally devoid of hindquarter sweat.

There is a fine line between good intentions and proper execution. Worn correctly, a jacket is an essential element for refining your wardrobe, setting you apart from the sickeningly casual masses and hopefully garnering a few female glances. Conversely, without the right approach you could wind up portraying a hillbilly at his momma's funeral or a chunky ten year old sloshing around in dad's duds.

Most men feel forced into wearing jackets, either out of social pressure or office obligation. They begrudgingly slip inside their resented uniform like a stupefied zombie instead of embracing a classic piece of menswear that can transform them from a drone to a Draper. The true beauty of a well tailored jacket, besides upping your style ante, is its versatility. Investing in a proper jacket will bridge the gap between rugged and refined. Paired with proper trousers, you will denote an air of sophistication, while switching to denim arouses casual charm. Allow me to pontificate:

The Basics:
As with most anything, you get what you pay for. A jacket can and should be worn often - pony up and purchase a well made piece. While there are many places that peddle a vast selection of jackets, they're often meant for the man that HAS to buy instead of the man that WANTS to buy. You have made a conscious choice and now is the time for discretion.

Be on guard entering a Men's Wearhouse, Jos. A Banks or similar store. They market to an older crowd that tends to want more conservative business looks. You, my friend, want style, not business. As an alternative, try department stores such as Macy's or Lord & Taylor or even Filene's Basement that sell more fashion minded brands like Calvin Klein, Tommy Hilfiger or Ralph Lauren. These labels keep abreast of the current trends and have various lines aimed at different demographics. Not to mention that shopping a department store (especially during sales) will offer style without causing your wallet to break out in hives.

Living in New York, I happen to be surrounded by specialty stores that I have come to prefer over other purveyors. These shops have a more concentrated design on what their brand produces which helps battle indecisiveness and overload on my part. I know exactly what I'll be facing before walking in each store. The price point may be slightly higher but it can help to narrow your focus and expand upon a garment's purpose. Take stock in their lookbooks for ideas. For instance, places like J.Crew actually promote deconstructing their suits to be worn as separates, which creates many styles with one purchase.

In the end $150 - $300 is an excellent price for a well made jacket. Think of it this way, you spend $50 on a bottle of scotch that will ultimately wind up in the toilet. Spending $250 on a jacket you wear 3 times a week seems pretty reasonable now, right? 

Beautiful fit off the rack, this flannel suit jacket
doubles as the perfect sport coat.

Fit:
First and foremost is fit. Don't even bother looking at patterns and styles until you know your correct jacket size. If you chose to ignore my advice, sirens will sound and hordes of beautiful women will laugh and throw pickle juice on you. Go ahead… think I'm joking?

Your jacket size is based off of your chest measurement.  Have a tailor, friend or family member measure your chest from the widest point.  This will give you a basis to begin trying on sizes. Most men wear their jacket too big.  From this inital measurement also try a size down from what the tape measure reads.  You might be surprised that the fit is actually more comfortable and makes you appear even beefier than you no doubt are.  Being young and naive, I was told for years that I was a 40 Long when in reality I am a 38 Regular. Nailing the correct size will instantly up your confidence by enhancing your frame instead of hiding it. Additionaly, don't assume you are a "long" if you hover slightly over 6'. Men are often put in Longs based on height ranges when Regulars are more than adequate. A few other fit details to consider are:

• One quarter to one half inch of shirt cuff should be peeking out - or if you're Sammy Davis Jr., an inch plus.
• Your shirt collar should stand about a half inch to an inch above your jacket collar
• You should be able to cup your hands underneath the bottom of your jacket when standing with your arms straight at your side. Trendier, more fashion conscious jackets may be cut slightly shorter, a feature I tend to look for in a casual sport coat.

Cuts will vary amongst different labels. I recommend experimenting with sizing before attacking the aesthetic or weeding out brands. J.Crew's 38 Regular fits me perfectly with minimal tailoring, while other brands offerings at that size are short in the arms or tight cross the chest and a 39R is required. A jacket should fit clean and snug across the shoulders and back, but not so tight to restrict movement. Be sure that the seam between the shoulder and sleeve falls exactly at the hinge of your arm. As long as the jacket fits in the shoulders, most everything else can (and should) be tweaked by a tailor.

Lastly, a word of advice on salesman. Approach them like Indiana Jones in a pit of snakes. Ferociously flail a torch at them to keep them at bay (and keep a whip nearby in case one gets too close). In many run-of-the mill retail shops I've encountered, these "experts" are simply commissioned workers trying to earn a paycheck. They are not trained in, nor care about, tailoring or style and will exploit your fear and intimidation to make a sale. Size up the salesman. Look at how old he is and if you approve of his wardrobe to see if your thoughts align. If he's dressed like he's attending the Republican National Convention kindly say "no thanks" and rethink your patronage. Being prepared is the safest approach. Know thy size and thy style and avoid being swindled into a "comfortable" sack jacket. 

Keeping cool all summer long in navy linen.

Details:
Once you know your size, next is to look for larger details of the jacket.

• The current (and classic) trend is that of the slimmer silhouette of the 1960s. Look for single breasted jackets with a slimmer notch lapel, between two and 2 3/4 inches. Notch lapels are the most casual and will pair nicely with jeans, while peak lapels tend to be more formal and are better left for suits and double breasted coats unless you have the swagger to rock it with confidence.

• Chose a 2-button or 3/roll-to-2 configuration for buttons. Employing a 2-button with a lower stance helps to elongate the lines that form the V of the jacket, making you appear taller and thinner. 3-button tends to cut you off at the chest, making you look stocky. Anything over three should be burned or donated to Sportscenter's wardrobe department.

• Center or side vents are equally acceptable, just make sure there is a vent! A center vent tends to be more American, while the side vents evoke a bit of British dandy. At this stage pocket types are probably not a concern but there are generally three types - flap, patch and besom or slit - with the flap being the most common.

• There are casual and traditional jackets. Casual blazers tout a softer, unstructured shoulder and are generally unlined. I find these more of summer style and recommend looking for a lined jacket with more classic tailoring.

Plaid with a ticket pocket, a little British flair.
And at $150, a steal from H&M.

Color, Pattern and Fabric:
• There is nothing more timeless than a navy sport coat. However, a charcoal gray in a 4-season wool is an equally safe option providing a nice contrast with the dark blue denim.

• Black is acceptable but I tend to follow the rule that black jackets are better left for undertakers, limo drivers, the Feds and clergy. Not only can it be harsh against paler skin tones, the color will not offer you the flexibility of year round wear. Black in June doesn't sound so cool, does it?

• Apart from style, the sport coat takes on the added responsibility of temperature control. Especially as Fall approaches, fabrics types can be an additional consideration - tweed, flannel, twill, corduroy… or if you're rich, cashmere! Cotton, linen and seersucker are better served for the warmer months.

• Think about pattern as well. Herringbone, houndstooth and subtle plaids are all classic patterns and will pair nicely with jeans. 

Cotton Chino - A nice alternative for Spring into Summer

Final Assembly Required:
You might think that once you secure the perfect jacket you're finished - that you can safely troll about feeling confident that you look cooler than John Wayne on a horse. Well, you would be mistaken. The next time you are out try to really concentrate on how many men are wearing jackets; and of them, how many actually look good. The key to pulling of your desired look is 50% jacket and 50% everything else.

I am going to assume that you are not a 1980's Miami detective or an LA nightclub promoter. You are a lad aiming to create a smart look that borrows from the rugged and refined portions of your manly arsenal. With that being said these few pointers will help you solidify your look and step out assured of all your hard work:

Item #1: NO T-SHIRTS! Some think it cool to juxtapose the casualness of a t-shirt with the refinement of a jacket. I, however, am not one of those people.  It looks sloppy, dated and pompous.  Some men can pull it off, but unless you live in Hollywood and look like Brad Pitt, the aforementioned douchebag alarm will sound like a fog horn on a Northeast shoreline. Let the jeans work the casual angle and keep it classy up top. Stick to a placated shirt with a stiff or button down collar (note: button down generally refers to the collar buttons, not the fact that a shirt buttons down the front).

Item #2: Speaking of t-shirts, invest in 2 packs of Hanes V-neck undershirts. A sure way to amp up your game is to nix the unsightly crew neck peeking out of your open shirt collar. By eliminating the round neck line of your undershirt and letting some chest show, it frees your dress shirt to amplify the elongating lines of your jacket. Instant de-schlubization!

Item #3: Wear darker wash denim in a straight fit. No whiskering, fading or boot cut. Simple, straight and classic will have you looking sharp. Opt for a more rigid denim that will hold the same clean lines as the rest of your wares. I recommend Levi's 514s or Gap 1969 in Authentic or Straight fit as a perfect starter pair at an affordable price.

Item #4: Kick the square toe shoes and sneakers to the curb. Better yet, give them to the dog as a leathery snack. Invest in a nice pair of rounded brown or caramel color brogues to complete your look. Black reminds me of boardrooms and funerals, while the lighter browns pair well with dark denim and are considered more relaxed. For something more casual think loafer, chukka or straight up rugged boot.

Item #5: Don't forget the pocket square! A crisp white square will instantly separate you as a man in the know. And if you're really feeling saucy, don't be afraid to dress the whole look up with a casual tie. Keep the collar unbuttoned and give off an elegant ease.

So in summation J/P here, in my opinion, is what you need to search for on your quest: a slim, notch lapel, 2-button, gray or navy, 10-month wool jacket with a center vent and flap pockets. These details along with the right fit will put you well on your way to attacking Fall in style.

**Much of the same advice on buying a suit translates into buying a sport coat as well. For more expert advice check out the below video via GQ and look for other videos on the GQ Rules section of Youtube. Also, browse through sites like Prepidemic's Piece by Piece to see first hand what a stylish jacket or suit can do with different wardrobe pairings.