Typically I write about money, health, or fitness. However, I’m going off the beaten path because I’ve recently had several officers and NCOs suggest that I write an article covering how to dress well, particularly geared towards guys transitioning from the military into the private sector.

The fact that they recommended this to me is flattering and hilarious at the same time. If you look at pictures of me from even a few years ago, you’d probably vomit in your mouth a little bit at some of my style choices. My favorite outfit may or may not have been baggy, boot cut jeans with Birkenstock’s, and my haircut made me look like I was 12. Fortunately, by nature of my previous job, I was forced to become what some people would consider a well-dressed man with a “glorious” head of hair.

During my first deployment with Ranger Regiment, I was put into a position where I was required wear civilian clothes and regularly interact with the State Department, the Inter-agency, and Foreign Intelligence Services. Talk about a culture shock! Those organizations may have been rife with “leaf-eaters” but MAN did those people know how to dress sharp.

I was told to bring some “business casual” clothes and a suit, but not too stress about it because the compound had its own tailor (naturally) who would hand-make fitted shirts and suits at a fraction of the cost in the States. When I showed up, he asked me all kinds of questions like:

“How many buttons do you want on your jacket?

“Do you prefer your lapels rounded or pointed?”

“Where do you want your pants to break?”

My response: “I DON’T KNOW! JUST MAKE ME LOOK LIKE JAMES BOND!”

I like to say that I started that deployment dressed like a boy and came home dressed like a man.

Bottom Line Up Front:

1. Wear clothes that FIT!
   • The way your clothes sit on your body affect the way they look to others far more than brand, cost, or material. Are your sleeves too long? Are your pants too short? Does your shirt pillow around your waist? Do your garrison OCP’s look like a maternity uniform?
2. Spend money on tailoring, not brands.
   • A $150 suit from Men’s Warehouse tailored to fit correctly will earn you far more points than a $1000 Armani suit that doesn’t fit well. I promise you, no-one that truly matters gives two sh*t’s how much your clothes cost or what brand they are.
3. Wardrobe Interchangeability
   • Don’t buy single-use “outfits”. Spend money wisely by buying things that you can wear with several other items you already own.
4. Understand the style culture of the audience you are interacting with.
   • What you wear to a construction job interview is vastly different from what you would wear to a boardroom sales pitch.
5. Follow the “One Step Higher Rule”.
   • Dress one significant level of formality higher for an interview than you would for a day on the job. If employees typically wear jeans and a polo to work; you wear khaki’s with a button-up and a tie to the job interview.
6. Dress appropriately to your age.
   • A man’s wardrobe should undergo subtle shifts as he gets older and takes on different roles in life. A 20-year-old wearing pleated khaki’s with loafers looks just as out-of-place as the 45-year-old wearing swag to his daughter’s communion.
7. Get a big-boy haircut
   • Say goodbye to that high-speed, low-drag, super HOOAH, high-and-tight. It’s time to find a barber that owns a pair of scissors.

Why it’s Important to Dress Well

Let’s be honest, style, for military men, is a hard thing to grasp. 99% of us are literally told exactly what to wear every… single… day. And we all wear the exact… same… outfit.

“Oh, it’s -23* at Ft. Drum and Carl forgot to bring his PT Jacket this morning? That’s too bad… I guess you’re all wearing Summer PTs while we do burpees in the snow.”

Nevertheless, putting in the time and energy to learn how to present yourself well will pay huge dividends when it comes to interviewing for a job. Here’s why:

“Your first impression is often your only impression.”

“Perception is reality.”

These two well-worn phrases are frustrating to hear because they are unfortunately 100% true. No-one wants to be judged only by their appearance, but like it or not, if you are completely honest with yourself, you know for a fact that every day you intuitively make dozens of snap judgments about people before they even open their mouths to speak.

It is much easier to reinforce an initial assumption than it is to force a change of opinion. By making the default assumption a positive one, you’re saving yourself an uphill struggle for correcting an unflattering first impression. Plainly, don’t be 1994 Dwayne…be 2014 Dwayne.

 

Now that we have covered WHY it’s important to dress well, let’s cover HOW.

1) Wear Clothes that Fit

Fit is absolutely critical. It doesn’t matter what of type clothing it is (t-shirt, polo, button-up, suit, jeans, shorts, etc), how much it costs ($10, $100, $10,000), or what brand it is (Levi, Express, Gucci, etc.)… if the clothes don’t fit, IT WILL NOT LOOK GOOD ON YOU!

When trying on clothes simply ask one question: “Does the item fit your body?” If not, skip it. It’s not worth wearing, no matter what its other merits might be.

The most general guideline for a good fit is that it should sit close to your skin without pinching or constricting. You shouldn’t feel the cloth tugging when you move around, but you also shouldn’t have any loose billowing or sagging.

However, every piece of clothing is a little different, so we’ll take a look at how to get the perfect fit for each item separately.

Shirt Fit

We’ll assume a collared shirt here so that we cover all the bases, but these guidelines work fine for T-shirts and other non-collared shirts as well. The only real difference is that a shirt you’ll be wearing untucked can be a little looser around the stomach and waist without it being noticeable.

• The shirt collar should rest on your neck with the top button fastened and not pinch it. If you can’t do that without feeling constricted, or if there’s a gap between the cloth and your neck, the fit is off.

• The shoulder seams should end right where your shoulders do. If they don’t reach all the way, or if you’ve got part of the seam hanging down your bicep, it’s a no-go.

• The cuffs should be long enough to cover the large bone in your wrist (the one directly above your pinky finger). If it’s shorter than that it won’t show properly beyond a suit or sports jacket sleeve. A straight sleeve or a slightly tapered one are both fine; the taper gives a better fit for most men.

• The hem should fall at least three or four inches past your waist so that it can tuck-in completely. If it has “tails” in the front and back, rather than an even hem, make sure the points at the side where the tails come together can tuck in, as well as the longer tails in front and back. You need the whole shirt to tuck, not just the longest parts.

• The waist is where a lot of guys are wearing too much cloth. If your torso tapers, your shirt needs to as well. “Slim fits” can help with that, and it’s a relatively minor adjustment for a tailor to take the shirt in as long as there isn’t too much excess fabric. Get as close a fit as you can manage off the rack and then take it to a tailor if you need more.

• Untucked: Sometimes you want to project a more casual appearance or you think tucking in your shirt will make you look like your dad. If done correctly, there is nothing wrong with untucking your shirt. However, length is critical. If it’s too long it will make you appear short and sloppy; if it’s too short, your stomach will show any time you raise your arms. Most button-ups are not designed to be worn untucked, so I recommend either getting them altered to be worn as such or purchasing a shirt specifically designed to be worn untucked. I also suggest rolling your sleeves while wearing your shirt untucked.

• Short Sleeve Shirts: Short sleeve polo’s and T-shirts are an absolute must during summers in the southeast. However, please please get one whose sleeves hug your biceps. Nothing makes your arms look tinier than wearing a short sleeve shirt whose sleeves flap like “sleeves of wizard”. There are two ways to look like you have big arms: 1) Do hundreds of bicep curls or 2) Wear a shirt that fits. The power is yours!

 

Jacket Fit

 

That being said, if you’re really going to get any benefit out of having your suits adjusted, you need to know the lingo and what adjustments a tailor can actually make.

More importantly, you need to know what a “good” fit actually looks like.

When you try on a suit, you’re looking for a good fit in what’s called your “natural stance.”

That means standing up straight, preferably in the kind of dress shoes you’ll be wearing with your suits, with your arms relaxed at your side. If the suit doesn’t fit well in this stance, it’s not going to move comfortably with your body either.

Practice standing in that relaxed, upright pose, and then start trying on suits in that posture. Look for a good fit in the following areas when you’re in your natural stance:

• shoulder
• seat
• trouser break
• jacket closure
• sleeve length
• jacket length
• jacket collar
• shoulder divot.

This excellent video covers the correct fit for each component.

Finally, always remember the “Sometimes, Always, Never” rule for suit jacket buttons (excluding ASU’s lol). Sometimes button the top button, always button the middle button, and never button the bottom button.

Pants Fit

In Ranger Regiment we have this thing called “If, And, Then” statements that we use for meeting “trigger” to strike a bad guy. Here is yours for pants:

IF you are man, AND you have a meat popsicle between your chafing thunder thighs, THEN no-one wants to see you in skinny jeans!

Thankfully, most men already understand this. The problem is that most guys go too far and get more room than they need, going from “comfortable” to “saggy.” and end up looking like this:

• Length is pretty easy to judge; the trouser legs should end where they just brush the tops of your shoes, or rest very lightly on them. This is why you need to bring the shoes you will normally wear along with you when you go shopping. If you’re not touching the shoe leather at all or you’ve got a pile of bunched-up cloth resting on it, the fit is off (see graphic above).

• The waist should be tight enough that you can’t pull the pants all the way off without unbuttoning/unzipping the fly. If it’s digging in or bunching up, it’s too tight. Aim for a fit in between those two. Make sure you’re fitting the waist where you want to wear it — on slacks, that should be up above the hips, at the natural waist. Jeans can be closer to the hips.

• The rise is the distance from the waistband to the place where the seams join the crotch. It should be as close to your body as comfort allows. A little room for movement is obviously necessary, but a lot of men are wearing pants with two to five inches of “sag” in the crotch. Get rid of that! You want enough room for everything you’ve got between your legs, and not much more. A saggy crotch will make you look like Justin Beiber.

• The seat can vary a bit from brand to brand. There’s no real numerical measurement for it, but it’s another place where you don’t want sag. A loose trouser seat makes your butt look big and soft. Find a brand that hugs your cheeks. You want just enough room that you can slip a wallet in comfortably.

Trouser styles can vary pretty widely, so take these as broad guidelines. Heavier-set dudes are going to want a little more looseness in the seat than skinny dudes. Just be sure you’re avoiding anything that’s uncomfortably tight or so big you can make the extra fabric sway by swinging your hips around.

Shorts/Bathing Suit Fit

Rule #1: NO CARGO SHORTS

Rule #2: NO GYM SHORTS WITH SOCKS & SANDALS

Rule #3: NO JEAN SHORTS WITH RUNNING SHOES & HIGH SOCKS

Rule #4: If you are a 45-year-old dad taking your four kids to Disney World, none of these rules apply!

 

Basic Guidelines

In all seriousness, shorts; like t-shirts/polo’s are essential in the summer but can be hard to pull off correctly.

Length: If you are a short dude, long shorts that go below the knee will make you look REALLY short. If you are a really tall dude, really short shorts can make show off WAY more leg than most people actually want to see. Ideally, you want the hem of your shorts to sit one to two inches above your knee. A 7-inch hem will be the money spot for most guys. Dudes over 6′ can typically get away with a 9-inch hem and dudes under 5’8″ can rock the 5-inch hem (see graphic below).

Waist: Unless you are a ripped dude rocking 8% body fat, do yourself a favor and a wear NON-ELASTIC bathing suit. An elastic bathing suit will simply make your love handles look even lovelier and make you feel self-conscious.

Good

Bad

Color: Stick with neutral colors like gray, khaki, black, blue, etc. Chubbies makes some really fun shorts in both design and color, and they can serve a purpose on occasion like a certain PT competition in Baraki Barak, Afghanistan (you had to be there lol). But do you really want to show up to your neighbor’s kid’s birthday looking like a highlighter exploded on your shorts?

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2) Spend $ on Tailoring, not Brands

Doesn’t it just grind your gears when you find yourself perusing through a Men’s Health, see a dashingly dressed dude, and think, “Hey that guy looks pretty cool, I could rock that outfit!” only to glance at the “Buy this Look” blurb and discover you would have to take out a 2nd mortgage on your home just to afford the tie?

It is really easy to get sucked into buying super “name brand” outfits as a status symbol to compare yourself with others or fall into the trap that you have to buy “bespoke” (handmade clothes) in order for them to fit well. If you can truly afford all that, great! Most likely, if you are a young soldier transitioning out of the Army, you can’t.

Fear not! It is absolutely possible to look sharp on a budget.

The absolute best way to save money is to buy clothes off the rack and get them tailored to fit properly. This applies to all clothes (Polo’s, T-Shirts, Button-ups, pants, etc), not just suits. I do this with all of my button-ups.

 

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3) Wardrobe Interchangeability

If you are shopping on a budget, you can’t afford to waste money on different colored shirts for every day of the week or matchy-matchy outfits that can only be worn to one occasion.

Instead buy a few, quality staple items that are versatile and interchangeable with one another. These items will depend on your lifestyle. If you work as a contractor for an oil refinery in Texas you probably don’t need a bunch of dress shirts, whereas if you work as an investment banker you need quite a few.

Obviously not true for all walks of life, but here a few go-to’s:

• A dark suit (dark blue or charcoal). A dark blue suit can be worn to many more occasions than a black one. Even if you rarely have the need one wear one (think oil refinery guy), it’s good to have one for when you need it (wedding, funeral, etc.).
• A solid pair of jeans. Sturdy, simple, and dark, with a nice close (but not tapered) fit. Good jeans can be paired with almost anything.
• A few solid or small-patterned neutral-colored dress shirts. You could wear these with a suit and tie for a formal business setting or with shorts, boat shoes, and rolled-up sleeves to a summer BBQ to everything in between.
• A few neutral-colored polo shirts. Same as dress shirts, fitted polo’s can be interchanged with many clothes for dozens of different occasions.
• A few neutral-colored T-shirts. It’s no coincidence that almost every Men’s Health cover (where the guy has his shirt on) sports a guy wearing a dark, fitted T-shirt. They do it cause it’s manly and women love it.
• At least two pairs of dress pants. Grey, navy, tan, or khaki. I suggest “J-style” or “5-Pocket” pants to prevent “pocket flare”.
• Two pairs of neutral-colored shorts. Shorts and a T-shirt, shorts and a polo, shorts and a button-up… just don’t do shorts and a suit jacket lol. Remember what we discussed about length above.
• Two pairs of casual shoes. Pick your style (oxfords, brogues, work shoes, boots, saddle shoes, etc.). This is how you dress up jeans or dress down nicer outfits. Random tips: Your belt color should match shoe color. Don’t wear black shoes with a blue suit. Avoid anything with a square toe. Women will absolutely judge your shoes.  Click here for an in-depth guide to footwear.

Watch this video on the how to build a versatile wardrobe (FYI: Yes, his pants are a tad too high):

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4) Understand the style culture of your audience

In 2012, 27-year-old Mark Zuckerburg wore a hoodie to a Pre-IPO launch meeting on Wall Street where he planned to ask investors for between $5-10 BILLION dollars to help fund Facebook’s launch into the stock-market. This did not sit well with Wall Street.

I think that’s a mark of immaturity. I think that he has to realize he’s bringing investors in as a new constituency right now, and I think he’s got to show them the respect that they deserve because he’s asking them for their money. – Michael Pachter

Apparently, ole Zuckerburg learned a lesson from this, because he shockingly did not wear said hoodie to testify on Capitol Hill about the misuse of Facebook user data by Cambridge Analytica.

The lesson here is that it is critical to understand your audience and the message that you are trying to convey. You can be an absolute genius, but if you don’t have the social intelligence to project a professional appearance in a professional situation; you can completely turn-off your audience.

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5) Follow the “One Step Higher Rule”

When conducting a job interview, figure out what an employee in the position you’re applying for would normally wear to work, and dress one significant level of formality higher than you would for a day on the job. If employees typically wear jeans and a polo to work; you wear khaki’s with a button-up and a tie.

Levels of Formality: The Four Categories for Interviews (courtesy of the Art of Manliness)

To break it down in a little more detail, here are the broad categories that you should be using as your “steps” of formality:

• Strict Business Dress
• Business Casual
• Casual
• Work Clothes

The Strict Business Dress Interview

Strict Business Dress is for when interviewing for a job that requires you to wear a business suit every day. If everyone you’ll be working with wears suits already, your suit needs to impress. Examples include

• Law firms and banks
• Most managerial or administrative positions
• Business consulting jobs
• Public relations, advertising, and similar high-skill white collar jobs
• Many political or highly-placed public service positions
• Most teaching/academic positions

It may also be a good idea for people applying to low-skill jobs in high-status settings – such as a secretarial position at a major financial institution. You want to look like you can fit in even if you’re not going to be the high-powered player yourself.

The Business Casual Interview

Business casual is for any interview where a full suit looks too aggressive, high-status, or ambitious. Think of showing up in a blazer and good slacks rather than a matched suit. Plan on wearing business casual to interview for any job that requires professional dress but rarely expects suits and ties:

• Many entry- or mid-level small business cubicle/office jobs
• Clerical and civil service desk jobs
• Upscale retail positions
• Most political office and campaign roles
• Tech-sector jobs
• Food service, particularly wait staff, bartender, etc.

It’s a safe default standard for basically any job interview where a suit would be overkill.

The Casual Interview

Casual dress is best for a job where there is no dress code, or only a very loose one, and typically a job where the interview process itself is fairly relaxed as well. However, you still want to look sharp.

• Typical retail stores, especially chains
• Casual dining, food service, etc.
• Manual labor (assuming it’s not a hands-on skills interview)
• “Under the table” part-time jobs (dog walking, nannying/babysitting, etc.)
• Customer service
• Very casual start-up environments

You shouldn’t dress casually for an interview unless you’re very sure that the job is a jeans-and-T-shirt or company-issued polo shirt setting.

The Hands-On or Skills Interview

It’s increasingly common to actively test skills during the interview process, especially in skilled labor positions like carpentry or construction.

Dressing for these is about impressing the interviewer with your preparedness as much as it is about style. When you have to make the choice between formality and function, err on the side of function.

• Construction
• Skilled labor (plumbing, carpentry, etc.)
• Some landscaping/gardening positions
• Farm or ranch work
• Factory floor jobs (machinist, etc.)
• Black Rifle Coffee Company

Just keep in mind that you usually want to dress by normal job interview standards unless you’ve been specifically told: “we’ll give you a chance to use the equipment” or something similar.

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6) Dress appropriately to your age

When you are 20 you probably shouldn’t be wearing fedora’s and when you are 40 you probably should stop shopping at Ed Hardy.

The point is that while there are classic clothing staples you can wear at any age; your style should undergo a subtle shift as you get older and take on different roles in life. It’s called growing up and maturing.

• Dressing Sharp and Casual in your 20s
  • The “breeding” phase: This is the stage of most men’s life where you are motivated by one massive purpose… to breed (without actually breeding lol), and your fashion choices mostly revolve around answering the question, “Will this outfit attract females?” During this stage, you can dress more casually and progressively, but you still want to strive for a look that says “I’m an adult, and you can take me seriously.”
• Dressing Sharp and Casual in your 30s
  • The “building” phase: This is the stage where you start to build and solidify the things you launched in the previous decade of life. Most men at this stage either settle into their current identify or make a massive pivot towards something new. You also start getting addicted to HGTV.
• Dressing Sharp and Casual in your 40s
  • The “dignified” phase: I’m not in my 40’s, but I’m positive that my priorities in the future will be vastly different than my priorities now. Who knows, I might even start caring about lawn maintenance.

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7) Get a Big-Boy Haircut

I saved the best for last. This is probably my favorite topic because the typical Army haircut has grown so ridiculous over the years, all under the guise of “standards and discipline.” We have gone from this:

To this:

Nothing in the Army Haircut regulation says that you must shave off your sideburns to meet the standard. In fact, you can have a completely normal, sharp-looking haircut and still be well within military standards and be considered a “good” soldier.

Pop quiz: What do all of these guys have in common?

I bet you said, “They all won the Medal of Honor”. While that may be true, the real answer is, they all won the Medal of Honor… WHILE HAVING AMAZING HAIR! I’d say that proves you can still be a pretty darn good soldier without having a high-and-hooah. In fact, some may argue they won the medal BECAUSE of their amazing hair, but that can be neither confirmed nor denied.

Get a clean, professional looking cut that actually requires you to use some product. However, don’t be like most guys getting out of the military who completely over-compensate and end up looking like Tom Hanks in Castaway. Try and strike a balance between the two extremes as both will turn-off most civilian employers. If you don’t know what to tell your barber besides, “Gimmie a skin fade with a 4 on top,” read this excellent article on How to Talk to your Barber.

In closing, remember what a wise Civil War general said on his deathbed:

Never trust a man without sideburns. -GEN Ambrose Burnside

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That’s it

At the end of the day, I firmly believe that most men share one common desire:

Respect.

Not in a, “You will listen to me because I’m more important than you…” kind of way, but in a “My opinion matters and people take me seriously…” kind of way.

How you dress is a huge part of that, but it is not the only part. How do you carry yourself? Do you look people in the eye? Do you firmly shake another person’s hand when introducing yourself? These are all important aspects that form how people perceive you without knowing anything about you.

While this article is mostly geared towards male soldiers who are transitioning out of the military and are looking for advice on how to dress well without spending thousands of dollars; anyone can easily apply these principles. Hopefully, this article provided a good foundation on how to do just that.

If you found this information helpful, please share it on your social media outlet of choice, and subscribe to my email list to receive more articles like this delivered straight to your inbox. Whether you are venturing out into the civilian world, or simply trying to impress a pretty girl, I wish you the very best of luck.

You’re Welcome