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April 20, 2022 7 min read

12 Ways to Dress More Confidently

Your intrinsic + physical qualities are your unique strengths -- embracing them is what dressing more confidently is all about! We’ve formulated some of our favorite guidelines for you to put into practice as you’re getting dressed each day.  


curly haired woman in natural straw fedora

1: Dress for Confidence

Want to know how to dress more confidently? The great news is that confidence is a skill you can learn + develop from any starting point. It’s something that comes from within + then is expressed externally. Confidence is about how you carry yourself when you’re out in the world + that includes how you choose to dress. 

Dressing confidently is a combination of so many factors, such as - fit, personal taste, color, body shape, skin tone, lifestyle, + even what society says an outfit means. We address all of these factors below, + give you tips on what clothes will look + feel the best for you. 

2: Have Confidence in Your Personal Style

Labels, labels, labels… as if! Fashion isn’t that linear + neither are you. Watch out + don’t get yourself stuck in a category rut. What do you wear that makes you feel like your most authentic self? When you figure out the answers to that question, you’ll be ready to develop a wardrobe that represents you + makes youfeel confident


 woman in lavender bucket hat 


3: Build a Confidence Boosting Capsule Wardrobe 

A capsule wardrobe is a collection of garments that serve as the foundation for your outfits. As long as you have these basic, yet, essential articles of clothing, you can work them into as many looks as you need for everything you do in life. 



The fundamentals of a solid capsule wardrobe can start with the very basics - your tees. Depending on what your body type is + what feels good on you - the tees you own vary in fit + neckline. You’ll have crewnecks + v-necks, form-fitting + loose - they can all be mixed + matched to begin your outfit of the day.



Dress it up or go with the cool + casual route. Any way you wear it, your blazer will have you crushing the day with confidence. 


Blue Jean

You know the ones - you fit into them flawlessly + they look good with your blazers, tees, + knit sweaters. You can wear them with anything - your platform shoes, heels, or flats.


 blonde woman wearing wool felt hat


White Top

A white top can communicate many different looks, depending on how you choose to style it. Pair it with slacks for your work meeting. Layer it under your open trench coat for a nice, yet relaxed vibe. 



When a shirt is a jacket, it’s a shacket! Your cashmere shacket can carry your outfit in many directions - wear it open with a loose tee, or button it up + stay snug with a pair of jeans. 

Versatility is important for a woman like you - you’ve got places to go + people to be! This doesn’t necessarily mean you need an outfit for everything. It does mean that you want different looks for all the things you do.


4: Confidence Guidelines for Your Skin

short brown haired woman in knit beanie


Dark Skin: 

You have beautiful dark skin, so contrasting colors will look amazing on you. If you’ve asked yourself, how can I look confident + elegant? Wearing white is your solution. Also, pastels like seafoam, coral, +light mauve will be a few of the colors you’ll want in your closet. 

Medium Skin:

Look for tints (hue + white) or shades (hue + black) that are either lighter or darker than your skin tone. This leaves you with a lot of options to match your complexion. 

Yellows could bleed into your medium skin tone, so be careful with those. Deep raspberry, navy, + olive will compliment your medium tones famously.

Fair Skin:

Avoid your skin from getting too washed out against light clothing - although you’ll still look impeccable in neutrals. You can bring out more of the color in your complexion with shades likewarm rusty red, charcoal, + burnt sienna. 

The colors you wear can enhance your mood, change your state of mind + complement your complexion, however light or dark. Use the above guidelines to get you thinking about what will look the best for you. 


5: Feel Confident With What's in Your Closet

long haired woman with brown fedora hat


First thing's first - appreciate what you already have in your closet. You have thoughtfully selected each garment in your wardrobe because of its sentimental value, color, feel, or you just like it because you feel good in it.

It’s always fun to figure out how to wear clothes you’ve had for a long time in brand new ways that you’ll feel confident about.

Which pieces in your clothing collection do you feel the most confident in + why? Start with the clothes you already know you feel confident in + build a capsule wardrobe that will have youfeeling great in everything you wear. 

6: Dress Confidently Using Color Psychology

Do you see ablack cowboy hat on the hero of that old western movie, or is it always worn by the villainous bounty hunter? Color has a massive impact on human perception - it can communicate anything you want it to if you know how to use it to your advantage. 

Not coincidentally, if you look at a nurse, you will probably notice that they wear blue scrubs. That’s because blue communicates warmth, compassion, + sincerity - all of the qualities you want in someone who takes care of you. 


women's pink fedora hat


Radiate tenderness, optimism, + kindness when you wear yourdusty pink hat. Pink evokes all of those feel-good emotions from the people around you, and all you’ve done is put on one of your favorite outfits. 

You want to feel like your best self as often as possible - for your family, your friends, + most of all, for yourself. On days that you need a little boost, you can rely on the colors you have in your wardrobe to make you feel like you can conquer the world.


7: Color for a Confident Look

You can wear all the colors of the rainbow - however, some hues will go better with the natural tones found in your skin than others. The colors that will look best for you depend on the colors of your skin. Whether your skin is darker, lighter, or anywhere in between - we have some well-manicured rules of thumb for you to follow. 


8: Get Inspired by Confident Dressers

brown haired woman in ivory straw wide brim hat


You’re living downtown + commuting everywhere you need to go. Take inspiration from the streets as you’re heading to your destination. Architecture gives you lines + angles that could translate to the hem of your next a-line skirt. 

Another fun mode of inspiration is to check out what other people are wearing. This will help you figure out patterns + silhouettes that you would like to see yourself in. People watching will also give you an idea of the clothes that you would never, under any circumstances, wear - that’s valuable information for you to know! 

If you can’t stop thinking about thatluscious velvet cardigan you saw someone rockin’ at the market, look for one you can wear. If you can’t stop thinking about that gorgeous sage hat your friend has been eyeing online, grab one for her birthday + get one in your size while you’re at it. 

Looking at what other people are deciding to wear is a fun way to get inspired + will teach you a lot about your own fashion instincts. 

9: Have Confidence in Your Shape

red haired woman in high quality straw fedora


Do you have pieces in your wardrobe that are teetering the terrible line between being uncomfortable + affecting your level of self-consciousness? Donate those clothes to the nearest women’s shelter + trade them in for ones that will fit your body the best. 

You don’t have room to worry about whether your shirt is too tight or loose between meeting deadlines for work + getting yourself to paint night with your gal pals. With all the things already running around in your headwear the clothes that will allow you to focus on the best things in your life. 


10: Confidently Dress for Your Body Type

women's summer bucket hat


Hourglass Body Type:

Time to accentuate your waistline - think of Marilyn Monroe for classic ideas on how to dress for your body. Fitted on top, tied at the waist, with a full skirt - this silhouette will let you show off your feminine figure + have you feeling as confident as ever. 

Tall Body Type:

If you can reach the glass ceilings you’re breaking, more power to you! High-waisted tie pants will fit your body type just right + they’ll create proportion between your torso + legs. Also, you can create more shape through your slender figure by wearing tops that add fullness - the leg of mutton sleeves are sophisticated + so in vogue right now. 


11: Dress for Your Life + Style

short haired woman with cream felt hat

Your wardrobe depends on your lifestyle. Your early morning pilates class is easier to wake up + get ready for when you have your favorite leggings to look forward to. And your commute downtown is a lot more fun when you feel confident in the layers you’ve put together. 

Whatever activities you fill your time with, the proper clothing will help you to look +feel your best in everything you do. 

12: Dress Confidently for Any Occasion 

You have your typical routines + then you have everything outside of that. You go on vacation or travel for work, you attend weddings + you dance at parties. For all of the wonderful events in your life, you want to feel confident in what you wear. 

Traveling is the best thing ever + you already know that getting to your destination can be an adventure all on its own. Layovers + flights are your greatest opportunity to wear clothes that are both comfortable and cute. 

Do the robot in any outfit + it will kill every single time - however, if you’re getting into some vigorous swing dancing, you may want to trade in your skirt for slacks. 


women's panama palm straw hat with chin strap

The key to confidence lies within, + you can express it through the things you wear. Find the clothes that exhibit your personality, fit your body type, + feel the best for you.  xx