Coming from a life of a military service, trying to enter the “regular” civilian lifestyle is not a seamless transition.

Whereas in the military, many decisions are made for you or predetermined by your role, civilian life leaves some of that responsibility on you.

This sudden dependence on self can leave some confused, especially those who spent decades in the military.

Tasks like building a viable resume, personal branding, and even deciding what clothes are appropriate for a civilian workplace can be foreign concepts that provide serious challenges to those entering a life after service.

You’ve Probably Heard the Phrase, “Dress for Success”

Dress for Success” – what does that really mean?

At some point in your life, someone has probably told you that.

As a military service member, dressing for success likely meant showing up in uniform with everything clean and polished.

But largely, it meant wearing the same thing the majority of the time.

However, building a business wardrobe for the civilian workforce requires a bit more thought.

In this guide, we’ll take a look at working wardrobes and help you gain a better understanding at what the civilian workforce expects from employees and candidates.

Whatever position you find yourself in, this guide will help you craft working wardrobes using clothing you already have and coupling it with some key pieces to help you stand out.

For the Men

Dressing professionally for men is, subjectively at least, a bit easier than it is for the ladies. That’s why we’re going to start with an overview of professional men’s fashion.

The key factors to pay attention to when attempting to build out a man’s working wardrobe are: shoes, shirts, jeans, suits, blazers and ties.

These elements are the core components to every outfit possibility for professional men’s fashion.


Shoes are one of those pieces of fashion that many will argue are not vital. You may even be of the mindset that you only need one pair of shoes to make any outfit work.

Today, we’re going to correct that notion. At minimum, to look professional, you’ll need to have two pairs of nice dress shoes. The absolute bare minimum for a professional, working wardrobe is two pairs of shoes – one black and one brown.

These two pairs of shoes will allow you to look well put together in almost any business outfit.

Black shoes with a brown suit or vice versa can kill your chances of being taken seriously. Even if it isn’t something you personally care out, don’t make assumptions that hiring managers or employers will feel the same.

Once you’ve established a base presence of quality shoes with two pairs, you can begin expanding into different complementary shades and styles. There are many different styles of shoes including boots, loafers, and more.


As a general rule, business professionals should have at least enough dress shirts in their working wardrobes for every day of the work week.

For example, if you spend five days a week in the office, you should have at least five dress shirts.

The nice part about dressing professionally as a man is that most outfit components are interchangeable. If you don’t yet have dress shirts in your professional wardrobe, when shopping, pick shirts that you could see working for various outfits.

Some examples of colors and patterns that are usable across various professional looks are:

  • A solid white button up-shirt
  • A pale blue button-up shirt
  • A simple patterned button-up shirts like vertical stripes
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    Solid colored wool or cashmere sweaters for the winter

In general, you should avoid over-the-top patterns except for in special situations. Stripes and other subtle patterns are mostly acceptable in the civilian employment sector.

Solid colored shirts can often be worn with both brown and black suits, blazers, jeans, and are very versatile components of your working wardrobe.

Black tends to be representative of formal business environments. So at the start, you should be mindful of how you utilize black clothing.


Jeans are a specific category of pants for a building out a working wardrobe because they will not be wearable in all situations.

Whereas dress pants, chino pants, or other khaki colored trousers are adaptable to most looks, jeans are typically reserved more casual outings.

As a business professional, we’d advise you to lose light-wash jeans altogether.

The only jeans that should ever be worn in a professional setting are dark and well-fitted jeans. Dark, well-fitted jeans are acceptable for business casual applications.

Suits & Blazers

This is likely an area where a post-service military man would be quite comfortable. A suit is one of the most timeless and longstanding ways to show that you are a professional business man.

From Don Draper, to James Bond, to Donald Trump, a good suit is a widely-recognized symbol of business know-how.

But, does just any suit do? Though a suit is one of the easiest looks to pull off, there are a couple of tips to keep in mind for building a working wardrobe.

It’s a good idea to stock your closet with one suit from the three major color categories: navy blue, black, and grey. Those three colors have a wide array of applications that spans across occasion and season.

With three good suits in your wardrobe, there will be very few situations you’ll find yourself wondering what to wear.

You may find a job where you don’t wear a suit every day, that’s becoming more and more common. But you’ll undoubtedly have to attend a business meeting, wedding, funeral, office celebration or other special-circumstance occasion at some point in your career.

Blazers and fitted jackets fall in the same general category of suits. They’re a step between business casual and business formal and, if you have a versatile one, you can dress up with almost any outfit.

When looking for a blazer, try your best to find one that will work across outfits. A good blazer can be worn with jeans, suit pants, khakis, over a sweater or dress shirt or in almost any fashion scenario.

Dressing Professionally for Women

Building a working wardrobe for a woman is slightly more complicated, but luckily, ladies leaving the military likely have a better sense of professional dressing than men do.

Plus, the most wonderful part of building a professional wardrobe is that it happens over time. There is no need to go to the department store and buy an entirely new wardrobe in one go.


As a working woman, it’s important to have a basic starter set of professional shoes.

If you like to wear heels, it’s good practice to keep them below three inches. Flats are acceptable in much of today’s workforce.

A good starting set of shoes is made up of neutral colors including: black, navy, grey and nude/beige.

Skirts & Dresses

Wearing a dress or skirt to the office is one choice that many working women make – though it is not necessary and some women do not feel comfortable dressing this way.

However, if you do, skirts and dresses can be very versatile tools in your working wardrobe. Two staple pieces are pencil skirts and sheath or fitted dresses. Pencil skirts, sheath dresses, and fitted dresses are flattering for most body types and typically don’t have any over-the-top variants or adornment.

To build your working wardrobe, find a pencil skirt or fitted dress in a range of neutral tones. These pieces can be used as an element of most work outfits, giving you the ability to look nice without having a huge closet – or fashion budget for that matter.


Where pants used to be unacceptable when worn by women in the workplace, we, as a society, have a reached a point in gender equality where pants are accepted by most employers of women.

If you do chose to wear pants in the workplace, keep in mind the length – that is the most important factor. Pants should not fall too far below the ankle but also should not reveal any stockings or skin. Also, ensure that you keep in mind your shoe choice when planning outfits as heels can make pants appear shorter.

A Functional Handbag

As a woman leaving military service, your relationship with accessories may be nonexistent. We’re here to tell you of the benefits that quality accessories can have on your professional life – in particular, a functional handbag.

A handbag extends beyond just a fashion statement, it’s also for storage.

When buying a handbag, look for one that is large enough to hold all of your belongings. But choose one that does not look too large.

Handbags should look sleek. For this reason, black is a great choice.

Don’t be afraid to spend a little bit of money on a nice handbag. If it is taken care of, there’s potential that it will last for years to come.

Building Working Wardrobes After Military Life is Easy When You Follow Some Basic Guidelines

Before reading this article, you may have been like many Americans who undervalue the importance of professional, working wardrobes.

Hopefully, this brief guide opened your eyes to the importance of professional fashion but also showed you how simple it can be to “dress for success.”

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