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.
Not on this list are the standard go-to’s like have fresh manicure, keep your make-up dewy, and hair styled. Of course, these things make a HUGE difference, even if you’re just wearing a sweatsuit. But today’s list a little deeper, to the real core of making daily style easy.
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
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 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.
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 up to date 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 also quickly create a monochromatic look – which is pretty much the epitome of chic.
Love bold color and pattern? Go for it! The 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 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.
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:
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.
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
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.
View this post on Instagram
❤️My favorite outfit combo: jeans, blazer and boots. . . These ankle boots by @sam_edelman have become my do-to. . They come in an array of colors, I’m wearing “whiskey leather” and they pretty much go with everything. . . I paid full price – and I’d do it again because they are that good. But they are on a crazy good sale right now. 👆🏼Follow the link in my profile for all the details. And comment below if you picked them up!
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 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 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.
Sign Up for Daily Content and Receive Our Free Classic Wardrobe Checklist