I started my own business in the fashion industry eight years ago as 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 lifestyle that are classy yet trendy. Why? My number one reason was wanting to help these women feel better about themselves and boost their confidence. I’ve always told my clients and readers to dress in what they feel most confident in because – let’s face it – confidence really is the best accessory a woman can wear!

There have also been a number of 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 in a more casual manner – in other words, dressing classy helps you fit the part. In fact, a number of 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.

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

7 Ways to Dress Confident and Classy Yet Trendy

1. Wear what you feel most comfortable in:

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 own 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.

If you’re not sure what items you feel good in, try and remember a time when you had something on that you really loved. Maybe it was job interview 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.

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.

2. Know your body type: 

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

1. 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, and more fitted items on the bottom, such as skinny jeans, to accentuate their smaller hips.

2. Banana, or straight (rectangular)

This body shape describes a person who has basically the same measurements on their hips and bust, and their waistline isn’t exceptionally well defined. This person should consider dressing proportionally on the top and bottom while also enhancing their waist.

3. 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.

4. 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. This person can usually pull of almost any outfit without much trouble.

3. Emphasize your best features and de-emphasize your least favorites:

Now that you’ve identified which body type you are, you should now consider what your best features are. Do you have really 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 obviously make me look taller, but the high-waisted ankle length denim also makes me look taller and thinner – that style of jeans makes my legs look longer with its 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.

4. Know what colors look best on you:

Based on your hair color and skin tone, certain colors might suit you better than others. 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 golds could look amazing on you. If you’re a redhead, then you probably look stunning in green, while I think blondes do really 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!

5. Find your signature style: 

I love this quote by Anna Wintour: “Create your own 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 literally 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 personal 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!

6. Dress for the occasion: 

I get tons of emails on a daily basis 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 on 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!

classy yet trendy

7. Be trendy on a level that 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 really 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 really 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!

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