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How to Look Stylish Every Day

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 dress simple but stylish day to day 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, including a classic black dress or pair of jeans. 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, don’t forget that you can always 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 



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🙋🏼‍♀️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 shapes 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 pieces.

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, or when I need to quickly elevate my look for special occasions, I can immediately up my style factor by throwing on a camel coat, grabbing a classic bag, and wearing a better shoe. 


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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. A capsule wardrobe makes this easy. 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. 

Don’t neglect 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. 


How to Look Stylish Every Day

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Wednesday 9th of October 2019

Yes to wearing black! I worked with a stylist many years ago and she told me to purge all of the black from my closet because it “makes 40-something women look older.” But it also makes one look thinner, pulled together and chic. So maybe I’ll keep it away from my face by adding a scarf or top?

Megan Kristel

Friday 11th of October 2019

I just think we should wear what we feel good in, right? I really loathe these sort of canned pieces of limiting advice women receive around what they "should" wear, and how they "should" look after a certain age. Yes to black ! :)


Wednesday 9th of October 2019

Love this!! I do feel black is overused though, especially in winter, and washes many women out (if worn near the face, I don’t care about black pants!) I prefer a gorgeous color (cranberry, royal blue, green) when the weather is dreary. Also, seems like many older women wear faded black items :( - maybe not following the 20 year rule!

Love your ideas about uniform-category outfits. So smart.

Megan Kristel

Friday 11th of October 2019

I agree if you're going to do all black it shouldn't be faded out. But for me, a red lip and black turtleneck is my 5 minutes to chic formula ;)

Suzanne Clarkson Umile

Wednesday 9th of October 2019

What a great post! This may be one that I print & tape to my closet door :-). Re wearing all black...I’m with you, sister! I’ve been stewing over what to wear for a Friday evening fundraiser that will be ‘business casual’. My immediate “ go to” would be black slim pants and black sweater with pops of animal print. But I keep thinking I “should” wear more color, more...not black. Well, Megan, thanks to you, I’m officially over that!


Wednesday 9th of October 2019

Thank you for this! I really appreciate your insight and wisdom.

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