We all know that we shouldn’t judge people by the way they dress.

Let’s be honest: we all do anyway.

As a small business owner, you need people to take you seriously. The bank manager, your suppliers, your clients, and your competitors — you want every single one of them to look at you and think that they are looking at success. That’s even if you are struggling to balance the books at the moment, or you still feel like a little kid pretending to be an adult.

The need to make your best impression makes dressing well into a solid business decision. But that’s easier said than done. You’re pouring all your assets and resources into your business; where are you going to get the time and money to invest in your dress?

Here are 8 tips and tricks for ways to look the look.

1. Know where to shop

Knowledge is power, and when it comes to knowing where to shop, that power is absolute.

Shop second-hand

Get more bang for your buck by shopping in thrift stores and second-hand stores, especially in wealthy areas. You’ll love that thrill of finding a new, with-the-tags-still-on, brand name dress on sale for a few dollars in a thrift store.

Wanna save the legwork? Check out Poshmark: the largest social marketplace for fashion. Poshmark is where people just like you can buy and sell awesome new or used clothing at super friendly prices.

See? Second-hand doesn’t have to look worn out.

Shop across departments

Here’s another smart shopping tip: set foot in the menswear department (for women, obviously! Men would be shopping there anyway.) It’s depressing how much cheaper the same clothing is for men. For example, simple buttoned shirts like this can be half the price in the menswear section, but they still look just as classy.


Shop online

If you spot something you love but can’t afford in a bricks and mortar store, don’t despair. There are some wonderful websites that are dedicated to helping you find the same item for a lower price, or guiding you to it once it goes on sale. Here are some good places to start:

  • HauteLook is your destination to find out which sites are having a sale, and how big the discount will be. Just make sure to check each site’s return policies before you get your credit card out. You don’t want to be stuck with half-price designer jeans in the wrong size.
  • Shop It To Me is an email newsletter service that sends you alerts about deals on your favorite brand
  • RetailMeNot.com brings you news about discounts, special offers, and coupons on fashion, retail, and clothing.

Shop consignment

You don’t have to splurge to look good. Low-cost outlet stores and consignment stores like Marshalls and TJ Maxx are a great place to turn when you need to freshen up your wardrobe, but you’re strapped for cash.

2. Timing is everything

Shopping in-season is the worst thing you could do to your wallet. That’s when prices are high and special offers are low. It’s much better to plan ahead and do your shopping out of season. That means purchasing your winter coat in April in the end-of-winter sales, and getting strappy sandals in October as the fall items are flying off the racks.

It’s worth noting that this works best for classic pieces that you’ll wear again and again. High fashion items might look past-it and outdated by the time you get a chance to wear them, but a classic, well-cut trench will see you through for a long time.

3. Build your wardrobe strategically

You need to approach your wardrobe with as much strategic planning as you give to your business.

Don’t allow yourself to impulse buy high fashion items that catch your eye. The chances are good you’ll never wear them. I have a bright red tulip skirt I bought a few summers ago. It’s buried in the back of my closet and still hasn’t been worn out of the house.

Here’s what to do instead:

Create a capsule wardrobe

Build a capsule wardrobe of high quality core items. It’s worth it to pay more for classic items that you’ll wear and wash and wear again for years, without them looking outdated, fading, or baggy. Then you can mix and match these core items with cheap layering tees, swap out scarves and belts, add blazers and jackets on top, and accessorize wisely.

Opinion is divided over exactly how many items you need in your capsule wardrobe, but the consensus seems to be somewhere between 3 and 5 basic pants or skirts plus 5 to 10 blouses or shirts, or else 5-10 dresses.

Here’s what to include in your capsule wardrobe:

  • At least one little black dress

You can wear it simply with heels:

Set a business-like tone with a blazer:

Mix it up with a scarf:

Or replace it with a little black pantsuit:


It literally never goes out of style.

  • A well-fitting jacket or blazer

You can get so much mileage out of a jacket or blazer that looks sensational, fits properly, and goes with everything. It’s a unisex piece of advice, because a well-fitting jacket looks good on both men and women.

Here’s an inside tip: take an inexpensive jacket to a tailor to have it fitted properly. It will transform your entire wardrobe. These little details make it instantly look expensive and bespoke. It’ll make you look good because it matches your lines, and you can wear it over almost anything: jeans, suit pants, you name it.

And a long, fitted jacket over a little black dress is the bomb!

A fitted dark blazer brings instant professionalism:


Stylish and sophisticated:

Adding interest to plain dark jeans and flats:

  • Boots

Remember, it was the boots that made Puss in Boots famous. They might not quite change your life in the same way, but they will become an indispensable part of your wardrobe.

I cannot stress enough how worthwhile it is to spend money on this item. Don’t go cheap on your boots. You want them to be strong, good quality, comfortable, and to last at least a lifetime. The style is up to you.

Dressing up denim:

With a dress:

Over the pants:

  • Dark jeans

If you thought that jeans have no place in a capsule business wardrobe, think again. Good quality dark jeans can be dressed up or down, so they can take you through a business casual day at the office all the way into evening drinks with friends and a night on the town.

Look for fitted or skinny jeans that match your body shape. They usually look more “professional” than baggy jeans.

  • A suit

This one might depend slightly on your business type, but most people need a good quality suit at least on occasion. You can usually get away with just one, but make sure that it:

  • Fits well
  • Is made of high quality materials that will wear well
  • Is a neutral color so that it goes with everything
  • Can be worn separately with just the jacket or just the pants/skirt

The neutral color goes with everything, but the tweed pattern makes it interesting:

You can’t go wrong with a classic black pant suit:

Tailored, classy suit:

Stay neutral

It’s always best to stick to a neutral palette as the core of your capsule wardrobe. Neutral shades go with everything and they always look professional.

Then you can liven things up with accents of color whenever and wherever you think it’s needed, using a colored tee under a neutral jacket; statement jewelry; or a bright scarf or belt.

Here’s a great example. Same suit, but totally different looks:

Double up

When you find an item of clothing that really works for you, buy a second one. This is particularly true for classic basics. Finding just the right pair of pants for the office is a quest in and of itself. You know, the kind that flatter you in all the right places, feel great, and look amazing. Once you track them down, buy two pairs.

It might seem extravagant now, but when you spill coffee on yourself as you rush out the door, or you get holes in the knees because you wear them every single day, you’ll be thankful that you have a spare or two waiting to step up.

4. It’s all about the accessories

It’s the little details that really make your business owner outfit. If you get these right, then the rest of the outfit will fall into place.

Try lipstick

You might not be much of a lipstick girl, but nothing says business woman like a full, shining set of lips. On the days when you’re struggling to keep your eyes open and you grabbed the first outfit that came to hand, your lipstick can save the day.

Bright red lipstick says “I’m in charge here“:

Fresh, yet confident:


Put your hair up

When your hair is swept up away from your face, it makes you look tidy and organized, and draws attention to your bone structure. You can go for a complicated updo, if that’s your style, but a simple bun or ponytail a la Kardashians is all you need. It also saves you a gallon of time in the mornings when you’re trying to blowdry your hair just right.


Give your nails some love

You don’t have to get a manicure every week, but you do need to keep your nails in good condition. That means no biting them, for a start. Keep them trimmed and not too long, and if you go for polish, make sure that the polish isn’t chipped or cracked.

Statement jewelry

Statement jewelry dresses up an outfit and gets you more mileage for the same clothing. Sometimes it’s all you need to turn your outfit from casual to business casual. Men, this is for you too; switching between a rugged or sleek metal watch can transform your look.

A simple shirt and a statement watch:


Power lawyer pearls and big glasses:

A ribbon, hair clips, or hair slides can jazz up a plain outfit:

5. What matters is what’s underneath

You’d be amazed at the difference that the right undergarments can make. A well-fitting bra is worth every penny, even if you’ll be eating rice and beans for a week. It changes your entire silhouette and makes every item of clothing fit better instantly.

Underpants need to be smooth; no one likes seeing bumps and lines through the layers. Wearing a slip beneath your dresses can solve this problem, and many others as well. It stops the fabric from clinging to your legs, smooths out the lines of your bra, and makes everything hang much better. Best of all, slips are very inexpensive. Buy them in flesh color; flesh-colored items disappear underneath even sheer white fabrics, so all that anyone will see is a perfect outfit.

6. Keep it clean

Whatever you choose to wear should be sleek, clean, and neat. Loose, flapping layers and fussy fringes take away from your professional appearance.

Keep it simple and don’t overdo it.

7. Keep it real

Unless you’re a high-powered lawyer, your business clothes don’t have to be formal, high-powered-lawyer suits. After all, business casual was invented for a reason.

You can still dress well and look serious and classy in jeans and a simple shirt. What matters is the way that you wear them.

If you’re running a lawn care business, for example, clients won’t expect you to be wearing a twinset and pearls, but they will expect you to look clean and businesslike.

8. Confidence is free

Ultimately, the clothes you wear matter much less than the way you wear them. Confidence costs nothing, but it adds hundreds of dollars on to the value of your outfit. At the same time, if you’re not comfortable in your clothes, it will show, and then even the most expensive outfit won’t be good enough.


So hold your head high, raise your chest, and keep your back straight. Whatever you’ve got on is the perfect outfit, so don’t let it down.