Skip to Content

How to Look Stylish Every Day

How to Look Stylish Every Day

If you are participating in our Fall Wardrobe Challenge, today’s post will help get you ready for the second have of the process!

Let’s talk about how to look stylish every day because it’s easier than you may think. It doesn’t matter your budget, lifestyle, or body type. All it takes is some upfront time and a little discipline to look your best, whether you are running around in yoga pants or headed to the office in a suit.

For over a decade, I was a personal stylist. I didn’t work with celebrities or high-profile women. I didn’t have clients with limitless budgets or closets full of couture. Instead, I worked with women like you. Hard-working, budget-conscious, busy – oh, so busy.

How to Look Stylish Every Day: Seven Easy Tips 

My clients were in all seasons of life: stay-at-home moms, seasoned executives, single professionals, and recently retired. While they were diverse, they all shared one thing in common: they wanted to look stylish within their lives without having to fuss and fret about it.

Today, I thought I would share what I learned from working and speaking with thousands of women. I didn’t pull these tips out of thin air. These are the strategies and advice that worked for my clients time and again. 

The standard go-to’s are not on this list, like having a fresh manicure, keeping your makeup dewy, and hairstyling. Of course, these things make a HUGE difference, even if you’re wearing sweats.

But today’s list is a little deeper, diving into the core of who some women just look great every day.  

They are practical, simple to implement, and will help you look stylish all the time. 

1. Get Rid of “Just Okay” 

The key to looking stylish is only to wear things you love. 

One of my biggest “Aha’s” was when I realized how many clothes women buy that are “just okay.”

Think about how many things you have bought just because (1) it fit, (2) it was on sale, (3) you needed something, or (4) all of the above. 

Almost every woman I know has an article of clothing or an entire outfit that they make do with, but they don’t love it or even like it. Sometimes it doesn’t reflex their style at all. 

If this sounds like you (and it probably does because this is all of us), get rid of it. I do this for a living, and I can immediately think of three to four things I wear that I am, at best, lukewarm about. 

2. Let Go of Dated Clothes 

How to Tell if Your Clothes are Out of Style

 

Related: How to Tell if Your Clothes are Out of Style

In a similar spirit, if you want to look stylish, please stop trying to get a lifetime’s worth of wear out of your clothes

Clothes. Wear. Out. 

Of all the advice I give, this is the one I get the most push back over. I promise you on all that is holy; if you are wearing clothes 20 years old, they are dating you. 

You are not supposed to keep clothes for decades. There are, of course, exceptions, but they are the exception. Even the most basic garment will become dated with time. This is simply because lines, cuts, and silhouettes change and slowly start to date your look.

Patterns, prints, and color combinations will go out of style too. 

How long should your clothes last? That’s a difficult question to answer because it depends on what it is and the frequency of use. While there is no specific expiration date, it’s safe to say goodbye if you are hitting the 20-year mark.

Staying aware of trends and the expected shifts in fashion will help train your eye to notice when a piece isn’t updated anymore. Also, ask your best friend, sister, or daughter; they’ll tell you the truth 🙂 

3. Choose a Neutral Color Palette

This tip is not for everyone; however, if you lean more classic and traditional, with a twist, stick to neutral, tonal colors is an easy way to look stylish.

Not only do neutrals mix and match easily, but you can quickly create a monochromatic look – which is pretty much the epitome of chic.

Love bold color and pattern? Go for it! The key to staying current is to evolve with the ever-changing cut and construction of clothes.

And as I mentioned above, designs and prints will date you eventually, too, so let them evolve within your wardrobe as time goes on.

4. When In Doubt Wear Black 

 

 

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 

 

🙋🏼‍♀️Do you need a few “going out tops”? . The kind you wear for drinks with friends or a date night? . Overwhelming, this is the biggest void in most of my readers wardrobes. . And it makes sense. After spending our days working and taking care of our families, on the rare night we can go out for a little, we have nothing that feels special . Isn’t that a crummy feeling? . Standing in your closets, flipping through pieces you either JUST wore to work or maybe they don’t feel fun or special. . So over the next few weeks I’ll feature some pretty and affordable pieces you can mix into your wardrobe so you have a few things on hand when you get a minute to have a grown up night out. . Today I’m starting with wrap-style tops. These are flattering for all body types and quickly dress up basics you already have. Like this textured faux wrap blouse from @jcrew ☝🏼follow the link in my profile for all the well priced, size inclusive options.

A post shared by The Well Dressed Life (@thewelldressedlife) on


 

When did people start hating on wearing all black? I find the resistance to wearing black baffling. All-black outfits translate across so many styles.

It can be artsy, euro, classic, city chic, anything! You can wear it unadorned or use it as a canvas to showcase statement jewelry.

Some of the chicest women in history made head-to-toe black a classic. So if you like black, wear it, it’s always in style, it’s simple, and it helps you look stylish on days you don’t want to think about what to wear.

5. Invest in Simple Upgrades

Three items you could spend on that will instantly elevate your look, especially in the fall:

a great coat in camel or dark grey

a better quality handbag in a similar neutral tone

and your everyday shoe.

If you are always grabbing your boots, invest in the best quality you can afford.

Spend your day in sneakers? Buy one that you can wear with outfits for a sporty yet pulled-together look. 

When you combine a higher quality item in your everyday outfit, you add a sophisticated element that creates an elegant style.

Related: How to Mix High and Low Fashion

One of my favorite things to wear in the cool weather is a turtleneck and jeans. It’s an easy go-to for me when balancing working from home and life with my kids.

But if I have to run out to an appointment or meeting, I can immediately up my style factor by throwing on a camel coat, grabbing a classic bag, and wearing a better shoe. 

 

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 

 

I love neutrals. Whether I’m investing in a piece or picking up a bargain I always opt for neutrals. So when I throw on an outfit it looks chic and sophisticated.

A post shared by The Well Dressed Life (@thewelldressedlife) on


 

Play around with the elements in your daily look to add a touch more style. 

6. Consider a Uniform 

When I reference a uniform, readers often think I’m suggesting you wear the same thing every day. That’s not necessarily the case. Of course, if you want to take the Steve Jobs approach to dress, go for it.

However, a more realistic way to translate a uniform would be to create different versions of your favorite, stylish outfits that you wear every day. For example, one of my “uniforms” for work is jeans and blazers. But I don’t wear the same jeans and blazer every day.


 

Instead, I use similar elements to build out different looks.

Some days it’s light washed jeans and a casual blazer, other days it skinny jeans and a moto jacket.

For a meeting, it might be slim-lined black pants and a sleek blazer.

By duplicating looks, I can keep my style harmonious and “feel” like me without being overly repetitive. 

7. Have Enough of What You Need

Think about how often you stand in your closet trying to build an outfit, except your favorite pants are at the dry cleaner, or you JUST wore that perfect white tank.

These are the items you need more of, not similar, but more of the exact same.

I own three pairs of black Theory ankle pants because I wear them so much. I also own multiple pairs of skinny jeans in dark blue wash, several of the same pure white tanks, and at least three of the same black crew neck cashmere sweater.

Why? Because these are building blocks to my wardrobe, and if I don’t have a black sweater on hand one day, I can’t create 3-4 outfits. That’s limiting and makes it difficult to look like your most stylish self every day. 

Consider your building blocks. What are the items you wear all the time, what’s constantly in the wash – create a list, and pick up a few more of the same.

This way, you’ll look stylish every day without feeling like you are reinvention the wheel every time you have to get dressed. 


Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please  follow on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

Learn about our mission to help women look and feel their very best, every day, here

Sign Up for Daily Content and Receive Our Free Classic Wardrobe Checklist

 

 


 

 

How to Look Stylish Every Day

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Mina

Sunday 19th of September 2021

Please give suggestions for "layering" in warmer climates. I'm in GA and only wear jackets (rarely coats) in January-February. I want to look classy and cool!

Tracy Gray

Thursday 16th of September 2021

Thank you for this!! There are many days when I stand in my closet and stare at my clothes wondering what to wear. I’m newly retired so I’m rethinking my outfits to fit my new lifestyle. Have to admit I sometimes stand in a store or even my closet (haha) looking confused and discouraged. But this article is perfect to help me figure out what I need like snd will feel comfortable wearing. Again thank you.

Megan Kristel

Friday 17th of September 2021

Thanks Tracy! Glad it was helpful!

Ann Bushle

Wednesday 15th of September 2021

Thank you for these tips. So true about a favorite sweater being at the cleaners, or slacks being in the laundry basket! I have purchased multiples of a basic tee or sweater that I like, but I usually feel compelled to buy it in different colors. Love this idea of multiples of the same brand , in the same color.

Megan Kristel

Friday 17th of September 2021

Thanks for the comment Ann!

Amanda

Wednesday 15th of September 2021

Any recommendations for "matching" blacks since there seem to be such a wide variety of black colored clothing...

Megan Kristel

Friday 17th of September 2021

Unfortunately, I think the best way is to eyeball it, since you need to see the colors in person, in natural light.

Ellen Lopez

Wednesday 15th of September 2021

Thanks for the great tips and so easy to implement. Love black but need that camel coat!

This site uses Akismet to reduce spam. Learn how your comment data is processed.