Career Wardrobes: The Small Business Owner | Men Style Guide

Step-by-step menswear tips for building your professional wardrobe

Universal rules of fashion aren't — choose the ones that fit your role in life.

This series of articles looks at clothing choices for men in specific, individual careers, from undergraduate college student to high-powered financier and everything in between.

Find the style and the menswear that suits you and your path in life!

Some professions are easy to dress — the banker with his daily suits is a predictable wardrobe, varied by pattern and color more than style of clothing. A business owner, in contrast, may have to wear a wide variety of outfits for different occasions.

The meeting with an investor demands a very different look from the sales pitch at a convention, and neither one is likely to be the same as the daily work wear.

The savvy business owner looking to build his wardrobe should avoid hard-and-fast rules (“You should have a charcoal gray wool suit and a red tie to wear with it”) and instead select flexible, multipurpose clothes that can be dressed up or down for different situations.

A few pieces of custom menswear can make a nice indulgence on the expensive end of the closet, while the staples can likely be filled in with traditional dress shirts or polos, but the fundamental goals are flexibility and distinctive style — standing out from the herd without spending investment-banker money on your wardrobe.

The Business Owner's Style: Creative and Dependable

As someone who regularly works face-to-face with employees, customers, investors, and pretty much everyone else involved with your business at any level, a business owner's look needs to be sharp without becoming intimidatingly stiff.

It should ideally communicate both creativity and energy — the qualities that help businesses thrive and grow — and the kind of dependable reliability that makes people trust you with their money.

The artist's wild patterns risk worrying customers or investors, while the Wall Street exec's power suits will scare off casual passers-by and intimidate employees, so aim for a middle ground of dress-casual menswear in most situations.

Daily Menswear: Eye-Catching Casual Clothes

For most businesses, suits and ties will be overkill for daily work wear.

Depending on how hands-on your daily responsibilities are they may also be physically impractical, so for most business owners, leaving the tie at home should be a safe choice on an ordinary work day.

That said, you don't want to look sloppy in front of customers or employees (and you never know when someone you need to impress is going to drop by), so the sharper end of dress-casual is going to serve you best.

Generally speaking, that's going to mean trousers and a sport coat (also called “odd trousers” and “odd jackets,” which simply indicates unmatched).

For most men, even a sport coat seems a bit dressy, which is why dress shirts and khakis have become the dress-casual staple — and that's exactly why you want to wear the jacket, rather than looking like everyone else.

There is nothing inappropriately formal about a suit coat that makes it odd to wear at work, and the cut of a classic men's jacket is considerably more flattering than an unadorned shirt.

Distinctive patterns can help you stand out, and are perfectly appropriate in a casual sports coat, so don't be shy choosing something with a touch of flair to it (but be aware that not all body types are well-suited to all patterns — several of my other menswear articles discuss specific bodies and the choices that look best on them).

If jackets are impractical at your job for physical reasons, or you just feel the need to mix it up, make your other casual options stand out.

A good fit is the best way to set a dress shirt or casual polo apart from other men's, since few people opt to have these tailored; keeping shirts sharply-pressed will also make them look sharper than the average working man's (since most men let their shirts go some time between ironings).

Add a bolo tie if you can pull it off, or just a regular tie to make the ensemble a little dressier, or swap the dress trousers for a pair of dark jeans to dress things down.

A vest can also make an eye-catching and rarely-seen alternative to a sport coat — and, with its nod to shopkeepers and newspapermen of the early twentieth centuries, is perfectly appropriate for the business owner.

Professional Occasions: A Suit for the Meetings

From time to time, even the most free-spirited entrepreneur is going to be called upon to dress it up for an interview, presentation, or other formal, professional occasion.

There is still freedom of expression here, but the rules are stricter and the stakes are likely higher — opt for a suit rather than trousers and an unmatched jacket, and break out the rarely-worn tie.

Charcoal gray is a popular suit choice, since it is versatile, suitable for all but the most formal occasions, and flattering to most men, but as a private entrepreneur, you can probably justify a dark brown or dark green instead if you want to.

The unusual colors will help you stand out, and may seem more approachable than the business-formal gray to some people as well.

If your budget will cover it, tailored clothing will be more comfortable in formal situations than off-the-rack (as well as more flattering). A single suit cut to your measurements is likely a worthwhile investment if you plan to wear it with any regularity.

Unless you live in a particularly warm climate, you probably also want to opt for a thinner, lighter wool — don't underestimate how much sweat a high-stakes meeting can generate until you've been through a few (a good V-neck undershirt beneath your dress shirt can help with this too).

Avoid brightly-colored “power ties” in favor of something with a simple, repeating pattern or (better still) a monochrome knit tie with a modest pattern woven into the fabric. You don't want the blank formality of a single solid color, but trying to out-power the power-players is picking the wrong psychological battle.

Your goal is to look as laid-back and confident as possible within the confines of appropriate business wear.

Personal Accents: Memorable Business Clothing

The simple act of wearing a sports coat over your daily dress shirts will already set you apart from the majority of businessmen, but the more memorable you can make yourself the better — it's hard to find a product or service that isn't provided by a good number of competing businesses, so represent yours as distinctively as possible.

There's no disadvantage to personal flourishes, so long as they stop short of ridiculousness — wear an unusual style of hat, if it flatters your face, or sport a pair of distinctive wing-tip shoes.

Tooled belts can draw comment, particularly with unusual belt buckles (but nothing too huge, unless your clients are primarily rodeo fans or ranchers), bow ties or pinned collars set you apart from all the other guys in neckties; pocket squares will always set your jacket a notch above most other men in the room — and so on. Be aggressive in adding small touches.

Sample Wardrobe: The Entrepreneur's Closet

To some extent, climate and the exact nature of your business will determine what you choose for your wardrobe, but a few basics should be constant for nearly all self-made businessmen:

Wardrobe Essentials – What Every Business Owner Needs

1 suit (solid color)
1+ pairs dress shoes, black Oxfords for the first pair
2+ pairs casual leather shoes
belts to match each pair of shoes
10+ dress shirts (more shirts means more mix-and-match options, and longer until you have to do laundry)
1+ ties (if you only have one, make sure it goes well with your suit)
2+ sport coats
5+ pairs slacks/dress trousers, dark and light colors
2+ sweaters
3+ polo shirts (if these are your preferred work wear, have a few more of them and a few less dress shirts)
10 undershirts, either sleeveless or V-neck
10 pairs comfortable undershorts (briefs or boxer-briefs may be needed with close-fitted trousers)
10 pairs dress socks (matched to the color of your trousers – try to have at least two pairs per pair of pants)
1 simple, leather- or metal-band dress watch

Wardrobe Options – Additional Styles for Businessmen

1 classic navy blazer (gold buttons, etc.)
5+ pocket squares
1+ pair leather gloves (black and then brown are the obvious first and second choices)
1 quality overcoat, wool or leather
1+ hat
dress sandals, moccasins, or other relaxed footwear
3+ decorative belt buckles
cuff links, collar pins, tie clips, etc.
boutonniere

For more information on professional wardrobes:
Career Wardrobes: Clothes for Every Profession – Series of articles on Google Knol
Men's Style Guide at ATailoredSuit.com