7 Ways to Dress Confident and Classy Yet Trendy

Last Updated on October 9, 2024 by Ryan

I started my own business in the fashion industry eight years ago as a personal stylist – this would include meeting with women on a one-on-one basis to help them with their wardrobe, perform closet audits, and create looks for them based on their lifestyles that are classy yet trendy.

Why classy yet trendy? My number one reason was wanting to help these women feel better about themselves and boost their confidence while dressing classy yet trendy. I’ve always told my clients and readers to dress in what they feel most confident in because – let’s face it – confidence is the best accessory a woman can wear! That’s why we choose classy yet trendy.

There have also been several studies done on confidence and dressing; hence the famous quote: “Dress for the job you want, not the one you have.” In one of the most recent studies, The Cognitive Consequences of Formal Dressing subjects who dressed up in suits and more formal wear performed better on tests than people who were dressed more casually – in other words, dressing classy helps you fit the part. Several studies have been done supporting the theory that the way someone dresses has a major impact on their level of confidence.

I love this quote by Rachel Zoe: “Style is a way to say who you are without having to speak”; this is so true. Whether we like it or not, people are making judgments about us based on what we wear every single day. With that said, trends change all the time, so wholly depending on them probably won’t help you become more confident, which is why you have to be classy yet trendy.

Do we know that the way you dress impacts your confidence level, so why not be up to your game and dress the best you can? Classy yet trendy can best be achieved by a look that’s simultaneously confident and classy yet trendy. I’d like to help you achieve a classy yet trendy style with the 7 simple steps below:

7 Ways to Dress Confident and Classy Yet Trendy

Wear What Makes You Feel Most Comfortable

When I say this, I mean it in the literal sense – if you aren’t comfortable wearing 5-inch heels because they seriously aren’t comfortable, then don’t wear them; it’s that simple. But more importantly, I’m referring to how certain garments make you feel when you put them on. Do you feel like yourself a.k.a. comfortable in your skin, or does it make you feel like you’re trying to be someone you’re not?  The main goal is to always wear items that make you feel happy and proud of who you are. When you look good, you feel good too. Again, it is classy yet trendy.

If you’re not sure what items you feel good about, try and remember a time when you had something on that you loved. Maybe it was a job interview, and you went on wearing a polished suit and some killer heels. Maybe it was when you were on a date wearing a pretty floral dress, or maybe it was even a casual event such as a picnic with your family. Whatever the event, the reason you remember what you wore is because that outfit must have made you feel good about yourself and fit into the classy yet trendy category.

For me, I feel most like myself and most comfortable and confident when I wear jeans, a jacket of some sort, and heels (ALWAYS heels). Why? When I follow this simple outfit formula, I feel my very best and can wear variations of this type of ensemble over and over again. Whatever that is for you (it’s different for everyone), identify it and wear it repeatedly! When you wear what makes you feel your best, your confidence is sure to shine through the classy yet trendy look.

Know Your Body Type

Here are the 4 most common body types and my recommendation for how each one should dress:

Pear, spoon, or bell (triangle upwards)

This body shape describes a person who has hip measurements greater than their bust measurements. If you are this body type, you should consider wearing items that accentuate your waist (as potentially your best feature) while adding a little volume to your upper body. You can do this by wearing brighter colors or prints and veering away from pieces that are too flowy or boxy which will hide your waistline.

Apple (triangle downwards)

This body shape describes a person who has broader shoulders and bust than they do hips. This person may consider wearing items that are bigger on top, such as oversized jackets or shirts made of lighter, flowier fabrics. You can opt for a shirt with a flare at the bottom or even add a belt to your look to define or accentuate your waistline. Also, pairing this belted top or flared top with a fitted pair of pants will highlight your curves.

Banana, or straight (rectangular)

This body shape describes a person who has the same measurements on their hips and bust, and their waistline isn’t exceptionally well defined. The key to dressing this body type is to dress proportionally; that is to say, when choosing your outfits, match the fit of the top and bottom pieces. If you’re dressing flowy on top, dress flowy on the bottom. Another tip would be to add a belt or use contrasting colors between the top and bottom pieces to define your waist.

Hourglass (triangles opposing, facing inwards)

This body shape (typically presented as the “ideal”) describes a person with hip and bust measurements nearly equal in size and a narrower waist measurement. With this body type, you want something that is going to spotlight your curves, not hide them. Opt for pieces that, even if they’re not tight-fitting, follow your natural silhouette. Try to avoid pieces that are going to accentuate either the top or the bottom significantly more than the other as this may cause unbalance.

Emphasize Your Best Features and Minimize Your Least Favorites

Now that you’ve identified which body type you are, you should consider what your best features are. Do you have pretty long legs? Perhaps you possess a gorgeous long neck and well-defined arms? Or maybe it’s your waistline that’s your best feature? Whatever that is for you, identify it and dress accordingly.

You also need to identify your least favorite areas – maybe your waist, hips, or arms. Mine is my height – I’m 5’4”.  To work around this, I almost always wear heels and high-waisted ankle-length denim.

The heels make me look taller, but the high-waisted ankle-length denim also makes me look taller and thinner – the style of jeans makes my legs look longer with their higher waistline. I always wear a v-neckline too, which makes me look taller with more skin showing between my waistline and shoulders.

It’s these subtle tricks that make the biggest difference!  The key is knowing which clothing items to wear that highlight your best features while drawing attention away from those you don’t like. Finally, keep in mind that this is all about making you happy, so your own opinion matters more than what anyone else will tell you.

Know What Colors Look Best on You

Based on your hair color and skin tone, certain colors might suit you better than others. After hair color, the undertone is the next most important thing to take into consideration when choosing colors. Does your skin have cool or warm undertones? Don’t know if you’re warm or cool-toned? No problem! There are a few tricks you can use to find out.

When looking at the veins in your wrist, greener veins usually indicate warmer undertones, while blue or purple veins indicate cooler undertones. The next test would be what color of jewelry looks best on your skin. If silver looks more natural, you probably have cooler undertones, while looking better indicates warmer undertones.

Now that you know your undertones, we can talk about which colors look best on each. Those with cool undertones tend to look better in pastels, lighter colors, and blues of any shade. Those with warm undertones tend to look better in brighter colors, along with any shade of red, orange, or yellow.

There is more to choosing your colors than an undertone though. Hair color plays a role as well. Blondes with fair skin might choose jewel tones because these bright colors add extra contrast. On the other hand, if you have darker or olive skin, then warmer colors such as corals and gold could look amazing on you. If you’re a redhead, then you probably look stunning in green, while I think blondes do well with soft summer colors like pink and teal blue.

However, if you’re not sure or don’t have personal favorites, you can always go by which color you were wearing when you get the most compliments on your outfit. If someone has ever told you that “you look really good in that color”, consider wearing that color more often! For me, that color is blue – a really pretty teal blue.  Now that I think about it, every additional compliment is another reason to make me want to wear that color more often!

Find Your Signature Style

I love this quote by Anna Wintour: “Create your style – let it be unique for yourself and yet identifiable for others”. I’ve been told by many people since I was in high school that I have a very particular style, and I couldn’t agree more.  From the very young age of four, I’ve loved wearing jeans. I even remember getting my first pair of heels from my sweet neighbor when I was just four years old, and I wanted to wear them every single day!

Today, denim and heels are crucial parts of my go-to looks. For that reason, I’m very decisive about what to wear and how to put outfits together. I even named my blog “So Heather” because whenever my friends would see a piece of clothing that looked like something I would wear, they would call it “SO HEATHER!” For some of you, this look may not come as quickly or naturally. If that’s you, my suggestion is to refer back to item number one on this list: go with whatever you feel most comfortable and yourself in, and that’s your answer!

Dress for the Occasion

I get tons of emails daily from clients asking what they should wear to a certain event or party. I always ask this question first: what is the dress code?  For most parties and events, a dress code is usually listed. If it’s not listed, always err on the dressy side! 

I always say it’s much better to be overdressed than underdressed. For example, if you’re going for a job interview, the first thing you need to do is find out what type of company it is and what the environment is like.

If it follows the traditional corporate style where everyone wears a suit, wear a suit. If the environment carries a more laid-back, business-casual vibe, then you could go with that; even so, I would still recommend erring on the dressier side.

On the other hand, if you have a wedding to attend, find out where it is and what time of day it is before deciding what to wear. Weather plays a large part in determining what you should wear to certain events, so be sure to check it out before picking out your chic ensemble. When in doubt, seek advice from people who will also be attending the event, and remember – always err on the dressy side!

Be Trendy at a Level You’re Comfortable With

Trying new trends is always fun, and I frequently recommend trying new things out. However, don’t invest a ton into trends, especially if will only wear them for a short time. Trends come and go, so try out just one or two a season – ones that you love and will wear from time to time.

Again, this depends on what you’re comfortable and most confident in – if you find something trendy that you feel very confident in, then, by all means, wear it! However, if you’re not sure or hesitant about trying a certain trend, there’s probably a reason you don’t fully love it; my recommendation would be to skip it.

Remember: just because something is trendy doesn’t mean you have to wear it. Only wear things you love and, more importantly, wear things that make you love how you feel!

Confidence is our best accessory and the way we dress impacts our confidence. My goal is still the same as when I started my own business seven years ago. To help women look and feel their best. That’s why my best suggestion is a look that’s confident and classy yet trendy. I hope these seven above tips help you achieve just that!