10 Ways to Dress With Confidence Every Day

Remember: attitude is everything.

By Katherine Fluor
vanity fair, dressing with confidence, tropical, lunch, summer

You know that feeling when you need to be on your A-game for a big event, but it’s just not happening? We’ve been there, and all too often, it’s what we’re wearing — or what’s under our outfit– that’s getting in the way of feeling like the best version of ourselves in the moment. Since everyone on our team is juggling busy schedules, photo shoots, and after-work commitments (often within the same day), we’ve learned from experience how important it is to feel comfortable in our own skin. And since that’s a key part of living life #likeyoumeanit, we’re teaming up with Vanity Fair® Lingerie today to share our tried-and-true secrets to dressing with confidence. Since Vanity Fair® is always our team’s go-to for quality bras and underwear that provide all day comfort and support, we love partnering with them to share our tips for dressing with confidence – because it always starts with what we’re wearing under our clothes.

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.

At last week’s team lunch at one of our favorite local spots, Last Straw, we shared what goes through our heads when shopping for new wardrobe pieces, how we’ve discovered our personal styles, and our biggest pet peeves when outfits just aren’t working. Read on for our 10 secrets to dressing with confidence, tested and approved by yours truly.

vanity fair, dressing with confidence, tropical, lunch, summer

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 also give you time to borrow or buy things you don’t already have that will help make the perfect outfit. When I plan ahead, I know I can always walk out the door feeling confident (and on time!) –Kat

vanity fair, dressing with confidence, tropical, lunch, summer

2 – Have the right undergarments.

For me, the perfect outfit starts with what’s underneath it. To feel confident in my outfits (especially in my summer whites), I need my undergarments to fit well, virtually disappear under my clothes, match my skin tone, and be comfortable. The new Vanity Fair® Nearly Invisible™ collection checks all these boxes, and is always my go-to for quality bras and underwear that I know will work well with whatever I decide to wear. If I’m looking for a strapless, wirefree, or underwire bra, I know I can count on my new Nearly Invisible™ bra –its perfect fit and flawless edge design that lays flat against my skin make me feel comfortable and confident, no matter the outfit. –-Kat

vanity fair, dressing with confidence, tropical, lunch, summer

3 – Invest in Quality pieces.

I once read that while looking at clothing prices you should keep in mind “Price Per Wear,” which has been a game changer for me when shopping.  For example, my favorite sneakers or jeans might be pricey on the front end, but if I wear them 3-5 times a week for a few years, the price per wear can get down to pennies! I’d rather invest in fewer, higher quality pieces that I know I will re-wear for years to come, opposed to purchasing multiple pieces at a lower price point that I only feel meh in. –-Caroline

4 – Wear clothes that feel like “You.”

I’m a big fan of dressing in line with my personal style. Of course it can be fun to experiment with other looks at times, but when I really need to bring the confidence, I like to wear clothes that really feel like ME. There are certain outfits where I really feel like myself when I wear them. I love neutral tones and shades that complement my skin and hair. It basically comes down to knowing what looks good on you and then owning it. –Camille

vanity fair, dressing with confidence, tropical, lunch, summer

5 – Outerwear Is Always In.

On my last visit to Paris, a friend who was living there at the time tipped me off to the reason Parisians always look so put-together: they always wear a jacket! I had never noticed it before, but after that, I realized that locals all around me were wearing an outer layer. I brought the tip home with me, and since then, I’ve used this wardrobe hack any time I want to give my outfit a chic boost, and it totally holds true! Even in the summer, a super lightweight layer magically polishes a look. -Chanel

vanity fair, dressing with confidence, tropical, lunch, summer

6 – Find the right fit for you.

Don’t spend time worrying about what number is stitched into the lining. Shop sizing varies, 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.

Did you know that 8 out of 10 women are wearing the wrong bra size? Find out if you’re one of them by taking the Vanity Fair® easy fit finder quiz — I know that I personally was wearing the incorrect size and had no idea! Wearing my correct bra size has been a huge game changer in my overall comfort and confidence levels. -Kat

vanity fair, dressing with confidence, tropical, lunch, summer

7 – Be picky about trends.

While it’s always fun to follow the latest in fashion trends, I try to be careful about which ones to add to my wardrobe.  I love picking one or two seasonal trends that are flattering to my shape, but skipping out on any that feel uncomfortable or inauthentic to my personal style (while the headband trend is adorable on others, it’s not for me this season.) –Caroline

vanity fair, dressing with confidence, tropical, lunch, summer

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

A neckline that plunges lower than you feel comfortable with, that strappy tank where the straps are always falling off your shoulders. I’ve learned the hard way, if an outfit is going to cause me to be preoccupied and not fully able to focus on the people I’m with, I either take it to the tailor or donate it.  –Camille 

vanity fair, dressing with confidence, tropical, lunch, summer

9 – It Starts From the Bottom.

If my shoes aren’t right, my whole day is ruined. That’s why choosing my footwear is usually the first thing I do when getting dressed in the morning. If I’ll be running around town, nothing puts a spring in my step like cute-yet-comfy sneakers. If it’s a dinner date, a pair of heels instantly make the occasion feel special, and make me feel sexy and confident. –Chanel

vanity fair, dressing with confidence, tropical, lunch, summer

vanity fair, dressing with confidence, tropical, lunch, summer

10 – 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 I’ve made a clothing misstep or worn something new that turned out to not be as comfortable as I thought, I do my best to forget about what I’m wearing and be the best version of myself. Smiling and making eye contact with those around you goes a long way! –Camille

*Sponsored by Vanity Fair® Lingerie.