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 

How to Look Stylish Every Day
How to Look Stylish Every Day

My clients were in all seasons of life: from stay at home moms to seasoned executives and single professionals to 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.

So 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. Rather, these are the strategies and advice that worked for my clients time and again. 

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

Get Rid of “Just Okay” 

The key to looking stylish is to only 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 due 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. 

Let Go of Dated Clothes 

How to Finally Let Go of Clothes You Don't NeedIn a similar spirit, if you want to look stylish, please stop trying to get a lifetime 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 that are 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.

You May Also Like
Three Cute Outfits with Black Jeans

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, if you are hitting the 20 year mark it’s safe to say goodbye.

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

Choose a Neutral Color Palate

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 also quickly create a monochromatic look – which is pretty much the epitome of chic. 

Love big bold color and pattern? Go for it! They key for you to stay current is to evolve with the ever changing cut and construction of clothes. And as I mentioned above, patterns and prints will date you eventually too, so let them evolve within your wardrobe as times goes on. 

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 for canvas to showcase statement jewelry.

You May Also Like
Buy Now, Wear Now and Later: J. Crew Polka Dot Top

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.

Invest in Simple Upgrades

Three items you could spend on that will instantly elevate your look:

a great coat in camel or dark grey

a better quality handbag in a similar neutral tone

and your every day 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 an element of sophistication 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 that you can upgrade to add a touch more style. 

Consider a Uniform 

Often, when I reference a uniform, readers 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 to 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.


 

You May Also Like
How to Wear Spanx Perfect Black Skinny Pants to Work

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’m able to keep my style to be harmonious, to “feel” like me, without being overly repetitive. 

Have Enough of What You Need

Think about how often you stand in your closet wanting to wear something, or could 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 Paige skinny jeans in dark wash blue, 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 always being washed – 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 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 View Post 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 consider following on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.


 

How to Look Stylish Every Day

24 thoughts on “How to Look Stylish Every Day”

  1. 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!

    Reply
  2. 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.

    Reply
    • 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 😉

      Reply
  3. 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?

    Reply
    • 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 ! 🙂

      Reply
  4. Great info! Easy to put into practice! Here’s a question you’ve probably heard before: many of the best looking outfits I see always have high heels. Indeed even your casual pics often include them. My work is business casual In front of the public and some days I’m on my feet almost 8 hours. I simply must wear comfortable shoes with minimal heel. It seems like the more comfortable the shoe the more matronly they look! How to polish off the outfit sans heels?

    Reply
  5. Thank you also for this! Like you, I like to wear turtlenecks in colder weather. My problem is that I cannot seem to keep from getting makeup on the neck! I have enough trouble keeping scoop-neck tops makeup-free, so turtlenecks seem especially daunting. Any tips? Of course, I might just need different foundation…;)

    Reply
  6. Color analysis is challenging and there are very few stylists that can accomplish this trait. Black should not be worn by certain individuals who have warm and soft coloring such as myself. I do not have any black in my closet and do not miss it at all.

    Reply
  7. I really enjoy your posts, especially this one. It’s advice I can use even as a busy “retired” woman who still wants to look good everyday. I live in the southwest, in the desert and many of your suggestions will not work for a season in our climate… we have a very long summer with a short fall, winter and spring. With that said, your suggestions easily translate into something that will work for me year round. Thank you!

    Reply
  8. Thank you! I’m printing this out. Best thing I did this year regarding my closet was purge all the “just okay” items, and give a close look at the condition of my footwear.

    I find it helpful to compile “Want” and “Need” lists, and refer to them each month to keep me on track, so l don’t randomly buy clothing for the very reasons you listed.

    Reply
  9. THANK YOU FOR THIS!! I have printed it and it is now hanging inside my clothes closet door. The advice and suggestions are exactly what I needed. I have a tendency to hold on to clothes for so long because they fit well or several people complimented me when I wore them. Sometimes it just for the compliment. And I do need to be able to create several outfits manipulating several of the same pieces. Also, my daughter who just entered the working world–also asked for a copy.

    Reply
  10. Thank you for the helpful hints. I’m a 57 year old woman, still working with “vertical issues”. I am 5’2”. I love to wear heels but cannot due to foot issues from years of wearing heels when I was younger. In my position, I also have many days of lots of walking and physical work so it’s just not common sense to wear heels but struggle with looking frumpy. And with summer quickly approaching I am not a fan of shorts on myself out in public. Look forward to future articles from you.

    Reply
  11. Hi Megan,

    I’m very grateful to you for all your styling tips . I was wondering if you could review the latest spring rend if wide leg jeans. I am spring shopping…and only 5’2” but I know I would feel very comfortable in wide leg pants/ jeans.
    I have been wearing skinny jeans for years and am looking for other everyday jeans that are stylish and still comfortable.
    Thanks!!
    Glynis

    Reply
  12. I love your tips! This post made me realize I have two closets and 10 bins in my attic which are probably just OK, or I did buy because it was in sale, or out of date! Thank you!

    Reply
  13. Hi Megan,
    I was colour -coded years ago..as an “autumn”..so black looks awful on me.
    Would I replace the blacks for you with a camel or taupe? I know my best colour is teal…just cannot fin it..and in a coat, it is too over the top for me!!

    Thanks,
    Valerie

    Reply

Leave a Comment

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