How to Look Stylish Every Day | The Well Dressed Life (2024)

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

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

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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 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 coatin camel or dark grey

a better quality handbagin a similar neutral tone

andyour 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.

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 tocreate 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.

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How to Look Stylish Every Day | The Well Dressed Life (4)

How to Look Stylish Every Day | The Well Dressed Life (5)

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As a seasoned expert in the field of personal styling, I draw upon over a decade of hands-on experience as a personal stylist, specializing in working with diverse women from various walks of life. Unlike some in the industry who cater exclusively to celebrities or those with unlimited budgets, my focus has always been on assisting hard-working, budget-conscious women – individuals much like the readership of this Fall Wardrobe Challenge article.

Throughout my career, I've engaged with women in different life stages, including stay-at-home moms, seasoned executives, single professionals, and recently retired individuals. The common thread among these women has been the shared desire to effortlessly incorporate style into their daily lives without unnecessary fuss or stress. My expertise is not theoretical; it's grounded in practical, real-world solutions that have consistently proven effective for the thousands of women I've worked with.

Now, let's delve into the concepts discussed in the article:

1. The Importance of Personal Style

The foundation of looking stylish every day lies in wearing only what you love. This involves eliminating items that are merely "just okay" and embracing a wardrobe that reflects your personal style.

2. Letting Go of Dated Clothes

A crucial aspect of maintaining a stylish appearance is recognizing that clothes have a lifespan. The resistance to discarding outdated items is addressed, emphasizing the impact of evolving fashion trends on one's overall look.

3. Neutral Color Palette

Choosing a neutral color palette is presented as an easy way to achieve a stylish and timeless look. Neutrals not only mix and match effortlessly but also allow for the creation of chic monochromatic outfits.

4. The Versatility of Black

Wearing all black is promoted as a versatile and timeless option that transcends various styles. It's highlighted as a go-to choice that simplifies the decision-making process on days when one doesn't want to think too much about what to wear.

5. Investing in Simple Upgrades

Three key items – a great coat, a quality handbag, and everyday shoes – are identified as worthwhile investments that can instantly elevate one's look, particularly during the fall season.

6. Considering a Uniform

The concept of a uniform is explored, not as wearing the same outfit daily, but as creating variations of favorite, stylish outfits. This approach provides consistency while allowing for creativity and personal expression.

7. Having Enough of What You Need

The article advocates for having multiples of essential wardrobe items to avoid limitations when creating outfits. This approach ensures that one always has the necessary building blocks for a stylish look.

By incorporating these tips, individuals can enhance their personal style, regardless of their budget, lifestyle, or body type. These strategies are not just theoretical but are derived from years of practical experience in the field of personal styling.

How to Look Stylish Every Day | The Well Dressed Life (2024)

FAQs

How can I make myself look stylish? ›

  1. Good grooming. A stylish look always starts with good grooming. ...
  2. Choose neutral colours. Neutral colours serve as a fantastic base: think black, grey, navy, tan and white. ...
  3. Shop versatile on a budget. ...
  4. Pay attention to shape. ...
  5. Find a good tailor. ...
  6. Accept hand-me-downs. ...
  7. Take advantage of accessorising. ...
  8. Know your measurements.

What makes a woman look classy? ›

If you're trying to be elegant, start by wearing classic styles of clothing, like knee-length skirts and tailored button-down shirts, and choosing clothes made from high-quality fabrics, like silk and satin. Never too baggy, never too tight; the clothing of an elegant woman looks like it was made to fit just her.

How to look effortlessly stylish? ›

Neutral colors pretty much never go out of style.

In order to look effortlessly stylish, you're going to want a more timeless look, which means sticking to more muted and neutral colors. This can, however, be broken up with bold accent colors, especially on accessories.

How to be more stylish female? ›

12 Habits Of Extremely Stylish Women
  1. PAY CAREFUL ATTENTION TO GROOMING. ...
  2. EMBRACE THE CLASSICS. ...
  3. PLAN YOUR OUTFITS THE NIGHT BEFORE. ...
  4. GIVE YOURSELF PLENTY OF TIME TO GET READY. ...
  5. CHOOSE THE RIGHT UNDERGARMENTS. ...
  6. GET INSPIRATION FROM OTHER STYLISH WOMEN. ...
  7. ONLY WEAR THINGS THAT FIT AND FLATTER.

How to look more glamorous? ›

How to Look & Act Glamorous
  1. Wear clean, well-fitting, flattering clothes that match or share a color palette.
  2. Stay on top of your personal hygiene.
  3. Style your hair and put on makeup in a way that makes you feel confident.
  4. Accessorize with tasteful jewelry, sunglasses, watches, and/or bags.

How to dress classy and look rich? ›

Cultivate a high-end look through minimalist shapes, neutral colors, and quality fabrics. Look for clothing or accessories crafted from luxurious natural materials. Opt for simple yet classic designs with earth tones and neutrals like black, white, beige, and navy. Make your style exude sophistication and class.

How to look smart and attractive? ›

12 Proven Ways to Look Smarter Than You Really Are
  1. Brush off your middle initial. ...
  2. Take out the contacts and put on the glasses. ...
  3. Focus on looking bright-eyed. ...
  4. Put down the beer. ...
  5. Skip gargantuan polysyllabic words. ...
  6. Make eye contact. ...
  7. Ask questions rather than make statements. ...
  8. Dress to impress, but keep your assets covered.
Oct 15, 2018

How to dress well as a lady? ›

One of the most important parts of dressing like a lady is showing skin sparingly. You don't have to only wear pants and shirts with high necklines, but try not to expose too much cleavage or wear skirts and shorts that are super short. It's also a good idea to avoid wearing excessively tight clothing to stay classy.

How to look well turned out? ›

How to Look Put Together
  1. WEAR CLOTHES THAT ACTUALLY FIT. In the words of Stacy and Clinton from “What Not to Wear”, “if you don't have fit, you don't have style”. ...
  2. ENSURE YOUR CLOTHES ARE IN GOOD CONDITION. ...
  3. WEAR FLATTERING CLOTHES. ...
  4. INCLUDE YOUR PERSONALITY. ...
  5. ADD FINISHING DETAILS. ...
  6. BE CONFIDENT.

Which color looks classy? ›

Color combinations of black, beige, brown, gray, white and pastel colors. We believe that the colors listed above can be the easiest way to instantly change your outfit so that it looks more expensive.

What colors make you look elegant? ›

Neutral colors are often the epitome of elegance in fashion. Black, white, creme, grey, beige, as well as muted tones of green and brown, are some of the best shade choices to complement an elegant outfit.

How do I look effortlessly elegant all the time? ›

An effortless chic look is only complete with the right hair and makeup. Keep your makeup natural and minimal, focusing on glowing skin, groomed brows, and subtle lip color. As for your hair, think loose waves, a messy bun, or a sleek ponytail — anything that looks effortlessly elegant without appearing too fussy.

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