9 Ways to Dress with Confidence, Every Day

You know that feeling when you want to be on your A-game for a big event, a meeting, a date, or a social outing and instead you feel like you’re anything but? You want to look good and feel good in whatever you’re wearing and whatever you’re doing… but sometimes it’s just not happening. We’ve all been there, and often, it’s what we’re wearing that’s getting in the way of feeling like the best version of ourselves in the moment.

Deciding what to wear in the morning may seem like a simple task, but it makes a major difference in how you go out into the world and interact with others.

Here are 9 secrets to dressing with confidence, so you can get out there and shine.



1 – Plan ahead.

There are few things more frustrating than feeling like you don’t have the right outfit at the ready for an important occasion. Instead of waiting till the day of to pick out your wardrobe, plan ahead and try everything on so you’re not left rushed and scrambling to find something last minute. Planning ahead will give you time to envision exactly what it is you want to wear so you can feel confident, and it will also give you time to borrow or buy things you don’t already have that will help make the perfect outfit. When you plan ahead, you know you can always walk out the door feeling confident (and on time!).

2 – Invest in quality pieces.

Consider this: while looking at clothing prices you should keep in mind “Price Per Wear,” which can be a game changer when shopping.  For example, your favourite shoes or jeans might be pricey on the front end, but if you wear them 3-5 times a week for a few years, the price per wear can get down to pennies! Wouldn’t you rather invest in fewer, higher quality pieces that you know you will re-wear for years to come, opposed to purchasing multiple pieces at a lower price point that you only feel “meh” in?

3 – Wear clothes that feel like “You.”

We’re big fans of dressing in line with your personal style. Of course it can be fun to experiment with other looks at times, but when you really need to bring the confidence, we recommend wearing clothes that really feel like YOU. We’re sure there are often certain outfits where you really feel like yourself when you wear them, right? For example, items that complement your skin tone and hair colour. It basically comes down to knowing what looks good on you and then owning it.

4 – Outerwear is always in.

Need a quick and easy wardrobe hack for any time you want to give your outfit a chic boost? Always wear a jacket. Seriously! Even in the summer, a super lightweight layer magically polishes a look.

Shop our Women's Outerwear

Shop our Men's Outerwear

5 – Find the right fit for you.

Don’t spend time worrying about what number is stitched into the lining. Sizing varies per brand in many cases, and as long as it fits you right, the label is irrelevant – remember, clothes are meant to fit YOU, not the other way around. Also, the right fit doesn’t just apply to what’s on the outside — if your undergarments are too loose… or even worse, too tight – you’ll be uncomfortable no matter what you put on over them.

6 – Be picky about trends.

While it’s always fun to follow the latest in fashion trends, try to be careful about which ones to add to your wardrobe. We recommend picking one or two seasonal trends that are flattering to your shape, but skip any that feel uncomfortable or inauthentic to your personal style.

7 – Don’t wear anything that’s going to need constant adjusting.

A neckline that plunges lower than you feel comfortable with, pants that always need pulling up, a skirt that always needs adjusting, or that tank where the straps are always falling off your shoulders… We’re sure many of us have learned the hard way that if an outfit is going to cause you to be preoccupied and not fully able to focus on the people you’re with, it should either be taken to the tailor, donated, or passed on when trying it on before purchasing in the first place.

8 – It starts from the bottom.

If your shoes aren’t right, your whole day can feel off. That’s why choosing proper footwear for the day is a great place to start when getting dressed in the morning. If you know you’ll be running around town, standing all day, going on a nice dinner date, or going out in less-than-desirable weather, choose your footwear accordingly and then pick the outfit to go with it.

Shop our Women's Footwear

Shop our Men's Footwear

9 – Remember: attitude is everything.

No matter what you’re wearing, walking out the door with good posture and your head held high is the quickest way to feel confident in any situation. Even if you’ve made a clothing misstep or worn something new that turned out to not be as comfortable as you’d thought, always do your best to forget about what you’re wearing and be the best version of yourself! Smiling and making eye contact with those around you goes a long way!

Leave a comment

Please note, comments must be approved before they are published

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.