Why do all my favourite clothes suddenly look like crap on me? This is so depressing. Out of nowhere, the sleeveless dress I’ve worn a thousand times looks all kinds of wrong. It’s not that it doesn’t fit exactly. It just fits differently in spots, and it doesn’t suit me anymore. Whether it’s that I’d rather show off different assets now or I want a more sophisticated, comfortable feel, I need to rethink how I dress. And according to style expert Lynn Spence, I’m not alone. She says we women spend decades honing our personal style but at some point, we have to re-evaluate. One day, we’re in our closets thinking Arggghhhh I have nothing to wear and then suddenly, it’s Arggghhhh I have nothing to wear that feels appropriate.

Over 40: 10 Ways to Dress for Your Age and Still Look Cool

Photo Credit: © Peter Reali

Here’s the thing. I don’t feel my age. At all. In fact, when I look in the mirror, part of me is still shocked there’s not a 16-year-old with heavy bangs and too much eyeliner staring back. I’ve grown up, and now that my age has crept over 40, my style age has some growing up to do, too.

So let’s start with this question: Who do I want to project? While there are no hard and fast rules about dressing for your age (OK, maybe just a few!), trying to compete with the younger me is a losing proposition. And yet, getting older better not mean morphing into a boring old frump or abandoning my personal style. I know this: Right about now, I need to rethink how I put myself together.

Ready to get started? Here are Lynn’s top tips to dressing when you’re over 40.

HOW TO DRESS YOUR AGE AND STILL LOOK AWESOME

1. HOW TO WEAR YOUR SKINNY JEANS Over 40: 10 Ways to Dress for Your Age and Still Look Cool

Do skinny jeans have a cut off age? No, but the way you wear them does. Tunics or dresses look great worn over a slim silhouette bottom, which makes your skinny jeans a keeper. Alternatively, if that’s not your style and you are in great shape, but don’t want to reveal too much when you lean over, opt for a higher waist cut. You may also want to consider balancing out your silhouette with a wider leg jean, like the new higher-waisted flares. In fact, there are many jean styles to choose from and wearing jeans when you’re over 40 is somewhat of a science you can learn. This Tweed Print Tunic Blouse ($119) looks great over skinnies.

2. HOW TO WEAR SKIRTS

There are so many flattering cuts of skirts. If pencil skirts are your go-to staple but are starting to feel constricted, there are other options. Try an A-line silhouette on for size. It is more forgiving and guess what? It looks just as great with flats as it does with heels.

3. HOW TO WEAR TIGHT CLOTHES

If you think it’s time to stop wearing tight, revealing clothes, then it probably is. But how do you abandon your signature look? Don’t give it up entirely; just be more strategic. Try pairing one form-fitting piece with a looser fit item to create balance.

4. HOW TO WEAR FLORAL Over 40: 10 Ways to Dress for Your Age and Still Look Cool

If you love floral patterns, feel free to keep them in your wardrobe. It’s the type of florals you choose that make all the difference. Try going with larger patterns and prints. Remember this: Ditsy florals tend to skew very young. This 100% Cotton Floral T-Shirt ($59) has a flattering print that won’t make you feel like a kid.

5. HOW TO WEAR BAGGY CLOTHES

If you decide that you need to make yourself over to look more age appropriate, be careful that you don’t go too far in the other direction. It’s fine to start distancing yourself from fitted items that may not look or feel as good as they used to but avoid the oversize trap. Clothes need to fit properly at every age. If you’re going to wear baggier bottoms, such as harem pants, pair them with a fitted top, and vice versa. Avoid wearing oversize blazers and baggy pants together.

6. HOW TO WEAR CLASSIC CUTS

Classic doesn’t have to be boring, and it won’t be if you add a twist. If you feel you need to move in a more classic direction but are a fashion rebel at heart, incorporate one piece that stays true to your younger self. A motorcycle jacket, for instance, can still work with a sophisticated black wool pant and simple sweater.

7. HOW TO WEAR ANIMAL PRINTS

Animal print aficionados need not despair. You are never too old for animal print but what you can do is adjust how you wear it. Stick with one featured item, for example a clutch or a skirt, worn with a solid coloured top—as opposed to Over 40: 10 Ways to Dress for Your Age and Still Look Coolan all over print ensemble. If you go with a full print, choose a simple silhouette such as a dress with clean lines. This Animal Print Dress ($199) is a simple way to feature animal print without overwhelming your look. 

8. HOW TO DRESS LIKE A TEENAGER

Just because you can, doesn’t mean you should. Many women today take great care of themselves and are toned and fit but wearing something that is clearly too young—a belly-revealing crop top or a micro mini—can make you look like you are trying too hard to stay young. Having a youthful attitude and dressing youthfully are two very different things.

9. HOW TO WEAR SHINY FABRICS

Love a little bling? If you gravitate to shiny fabrics, all you need is a small fabric adjustment. Instead of going all shiny, take a look at glossy finishes instead. This subtle change in fabric finish can be much more forgiving, drawing less attention to problem areas.

10. HOW TO FOLLOW TRENDS

If you love following the trends, do it! Just pare down the bells and whistles. If fringes or frills are all the rage this season by all means wear them, but keep it simple. Fringe gloves may work better than head-to-toe fringe, and a blouse that has a simple frill on the cuffs is more sophisticated than layers of frills. Over 40? Here's How to Dress for Your Age and Still Look Cool

About the author

Randi Chapnik Myers

Randi Chapnik Myers is Co-Founder and Content Editor of BrazenWoman.com, the only lifestyle site by women 35+ for women 35+. A journalist, blogger, editor and marketer, she specializes in custom content creation for publications, companies, brands and authors at RCMContent.com. Proud to call herself a social media addict, Randi is never far from a screen—even when she's out hunting for designer bargains.

  • Tracey

    I love Lynn’s advice! I bumped in Lynn about 2 years ago at Spanner – she was pulling clothes for CityLine show. I went about trying on my summer coloured pants and she commented by telling me go one size smaller – the pants will stretch! Great advice. Bought them and then went back & bought 3 more pair in different colours. Still have and wear them to this day!
    Yes I still stuggle with my clothes suddenly (ok maybe not sudden … but come’on) looking like crap on me. I have invested in great pieces and always fall back on my go-to pieces. Still trying to be stylish and a bit hip and comfortable all at the same time. *** sigh ***

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