How to Dress Professionally, Feel Confident and Look Stylish

How to dress like a professional woman - Visit to read some style tips on how to dress professionally

Five tips to finding the perfect professional dress - Visit to read some style tips on how to dress professionally

Stylish at Work Outfits

Being stylish at work can be a struggle. Five days a week we find ourselves staring into our closets debating on what to wear, worrying about professionalism, appropriateness, color, and any number of other quandaries. Yes, we can always default to trousers and a button-down shirt, like our male counterparts, but is that enough? Not for most of us.

The question of what to wear to work and how to dress professionally comes up a lot from my readers. They want to be stylish but conform to business standards, while at the same time be feminine and confident. This is especially true when they attend conferences, where they are often meeting people for the first time, speaking to large crowds, or doing the whole meet-and-greet at a booth or social function.

So it’s time to address this conundrum. My goal is to inspire you to dress professionally, while feeling confident and looking stylish. Because clothes can do wonders for a mood, for self-esteem, and the way you present yourself to others.

Let’s see what will work for you and how to dress professionally.

How to Dress Professionally for a Business Conference

In the fall I went to Boston for a five-day conference. My days were filled with keynotes and seminars from morning to night. I was constantly on the go and had little time worry about my appearance once I arrived. So I made sure that I planned my wardrobe carefully before leaving, to take that stress off my plate.

Knowing my schedule, I knew that I needed outfits (and shoes) that would withstand a lot of sitting and walking, wouldn’t wrinkle through the long days, and be appropriate for both a morning keynote and evening cocktails. These are challenges we don’t face with our everyday business attire. Going to work amongst familiar colleagues at our own desk is a whole different ballgame than a conference, where you need to give a great first impression but be yourself at the same time.

If you are anything like me, you want to put your best foot forward, and that doesn’t include dark-wash jeans and a nice shirt. We need to go one step further.

In this outfit, I wore a black-and-gray dress from Ann Taylor. It’s comfortable and will withstand wrinkles, while the bold square print and waistline detailing give it a feminine but professional feel. I’ve accessorized with some simple drop earrings and dainty watch, as well as a large tote to hold my wallet, computer, a pair of flats should I need them, and other necessities. The blue strappy heels are comfortable and add a bit of pizzazz to the outfit, while not looking too dressy.

Not only was this outfit stylish and professional, it packed easily without wrinkling or taking up too much room.

So let’s take a look at what is appropriate for a business conference and some suggestions for your look.

Five Style Tips to Finding the Perfect Professional Dress

I happen to like to wear dresses. They tend to pack easily, and I like variety of prints and patterns that match my style. There’s something about a print that allows you to stand out a bit from others, although wearing a solid-colored dress with a colorful accessory (scarf, statement necklace, shoes) will achieve the same effect.

Alternately, a skirt/blouse or trousers/blouse combination will work. Both can be stylish, so wear what makes you comfortable and confident.

When it comes to dressing for a business setting, keep 5 things in mind:

  • Length
  • Neckline
  • Sleeves
  • Fit
  • Color or Print

Professional Dress Length

The length of a dress or skirt should not be so short that you feel uncomfortable. Look for a length that ends right above the knee or, if you are tall, a mid-thigh length. This will make it easy to get up and down out of chairs and appropriately cover you if you are walking up stairs or on an escalator. When it comes to pants, the hem should end about 1 inch from the floor, allowing the front of your heels to show. If you are wearing ankle pants (with heels or flats), make sure they actually end at the ankle, too short or too long and they look sloppy.

Professional Dress Neckline

Necklines of both dresses and blouses need to be somewhat modest and not show too much—if any—cleavage. Leave the plunging V-necks and halters at home. That said, you aren’t required to wear turtlenecks either (although you certainly can, particularly in very cold climates). Try a happy medium, wearing a round or scoop neck, boat neck, square, keyhole, or collared style.

Professional Dress Sleeves

Usually, offices and conferences are on the cold side, so for dresses and blouses I usually opt for longer sleeves. You can go full-length with a cuff or try a three-quarter-length sleeve, which is said to be the most flattering. A three-quarter sleeve ends between your wrist and your elbow.

The lower the sleeve is on your forearm; the thinner your arm will appear. So a three-quarter sleeve length has many positives. It’s office appropriate, it’s the most flattering, it hides your arms if you’re self-conscious about them, and you won’t be as cold. In the summertime or in warmer climates, you can wear sleeveless or short-sleeves as well. For colder mornings, don a cardigan or jacket and as the day warms up, you can remove the layer as needed.

Professional Dress Fit

The fit of your garment is probably paramount. Fit = Appropriateness. Too tight is certainly frowned upon and looks unprofessional, while at the other end of the spectrum, baggy and ill-fitting clothes won’t do your figure any justice and tend to look sloppy.

Look for dresses that are loose but accentuate the waist. You want the dress to be figure flattering, but not just figure focused. A-line, shift, sheath, classic wrap, and princess style dresses are all good choices. (The dress I’m wearing in this outfit is loose but is ruched in the waist and has a nice cloth belt to accentuate the waist. This dress is the perfect mix of figure flattering yet appropriate for a business conference or office.)

If you like the idea of wearing skirts, the A-line is universally flattering, while pencil skirts or flared skirts (tighter at hips, flaring out mid-thigh) are also good options. Pants should be mid-rise or high-rise, either in a straight-cut or wide-leg style. Ankle-style is also appropriate as long as they are not skin tight. Make sure that the waist fits well and the pant is not overly baggy.

Professional Dress Color or Print

Your personal style will help dictate the color or print of your garment. When it comes to solid colored dresses, you’ll want to wear colors that look best with your skin tone. Of course, you can also go with basic black which will make everyone look nice, but dare to try a color like burgundy, midnight blue, red, or forest green. In addition to wearing colors that look good with your skin tone look for colors that go with the seasons.

And don’t be afraid of prints. A feminine floral blouse, businesslike pinstripe pants, or a houndstooth skirt breaks up the monotony of solids.

Professional Accessories

Everyone needs a few good accessories, and going to a business conference is not exception. Shoes, bags, jewelry and scarves help to define your style, and are often practical and useful items.

When it comes to shoes, the decision on what to wear will be dictated by the mileage you’ll be traveling within the conference and the formality of the conference itself. Typically a heeled or wedge closed-toe shoe is most appropriate. This can be a small kitten-heeled slingback or a 4-inch pair of pumps. Make sure they are comfortable for the long day, well maintained, and work well with more than one outfit.

Alternately, boots and flats can often be work. Heeled knee-high boots or heeled booties in leather or suede are good choices. Flats should be professional looking and either a loafer, ballet or pointed toe flat (with or without embellishments). Leave the sandals and tennis shoes at home.

Your handbag or tote should look as professional as you do. Make sure that it is in good condition and can adequately hold everything you need. There’s nothing worse than a half-open purse exploding with personal items. Steer clear of backpacks and opt for leather or vegan leather bags with zippers (for safety). Don’t be afraid to do color here. A stunning red back with a black outfit will make you not only stylish, but people will remember you!

Stay classic and simple with your jewelry. Studs, hoops, or small drop earrings, along with a classic necklace, bangle or watch is really all that is needed. No large gaudy statement necklaces need to be packed.

I find scarves to be an invaluable part of my travel wardrobe. They not only add a pop of color, they can keep the chill away on cold mornings or when the A/C is on too high. Try bringing one solid and one colorful scarf along. They won’t take up much room and I’m betting they will come in handy.

I hope this post answered some questions for you on how to dress professionally! If you find yourself needing advice on more business casual type of clothing for everyday wear or a conference, check out my post.

If you have a stylish at work questions, just send me an email, and I’ll answer you directly and add it to a blog post.

Stay Stylish,

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5 thoughts on “How to Dress Professionally, Feel Confident and Look Stylish

  • default avatar

    so beautifull and so cute

  • default avatar

    Hi Ms. V,

    This is another V, who loves your posts. I am a 23 year recent grad, I’m 4’10” and I weigh 105 pounds. I recently got a job, and I find it very difficult to shop business casuals. I went to many petite racks and couldn’t find the right pants. They’re too long to my legs. It would be amazing if you could suggest me any brands which you might have come across, and I love the bag you have in the pictures, can I know where to shop good leather/office bags?


  • default avatar

    I just discovered this site. Great ideas. Fabulous photos. A good guide for professional dress.
    Thank you!!

  • default avatar

    This blog is just full of great tips on how to look and feel great. This post is just another great one. Keep it up

  • default avatar

    it’s so detail, thank for your tips