Best Fashion Advice Over 40

When my oldest daughter, Lola, now 15, was little, I used to post some of her more adorable remarks on Facebook, saving them in an online journal of sorts. I know everybody thinks their kids are the cutest, but people often asked me if I would turn Lola’s one-liners into a book. It would definitely get a lot of laughs.

One of my favorites was when she pouted about her last name, Manley:

How could you say yes to Manley? Manley? Who wants a name like Manley? I’m going to change mine to womanly.

Lola, age 5

I wish I could promise you that my words of wisdom are as entertaining as Lola’s, but I can’t. They are, however, pretty useful, if I do say so myself. So here, some of my best, and most timeless, fashion advice, as chosen by the members of my Ageless Style Program. I’m just going to go ahead and call this Part One, because since this video was filmed, more tips have been added to the list.

Here, 9 timeless pieces of style advice.

An item of clothing needs to do more than just look good on the hanger. It needs to bring out your personal best. This means having specific criteria for an item to meet before it makes it into your closet.

It needs to check all of your boxes, or at least the most important ones. And the most important one, in my opinion, is color. Knowing the colors that flatter you and building a wardrobe around them means that you can make quick decisions when shopping and choose only those colors that bring out your best. After color, you want to find a flattering silhouette and a great fit.

So many women get frustrated with shopping because they see a pretty item on a website, or on Pinterest or IG, or a store mannequin, and they buy it in the hopes of getting that same look. Then, they’re disappointed when it doesn’t look the same on them. We have all experienced this, and it’s so discouraging.

This is the equivalent of buying a mid-century modern couch that you spotted in a spread in Better Homes & Gardens, putting it into your Tuscan-style living room, and wondering why your room doesn’t look like the magazine room.

Unless you look like the model, the clothes you are buying will look different on you. Looking for influencers and models that at least share your coloring, your age, or your body type can be helpful to get a better idea of how certain things will work on you in real life.

Stop blaming yourself for poorly constructed or ill-fitting items of clothing. Nobody looks good in everything, and many of our fit challenges come from the fact that clothes are mass-produced and sizing is inconsistent across brands. Just because a size 10 from one brand fits badly and is unflattering, that doesn’t mean that something is wrong with your beautiful size 10 body. It just means that, in this brand, you wear a different size. Or, perhaps, this brand isn’t cut for your body type.

For example, if I were to put on a pair of Good American jeans in my size, I would feel like something was wrong with my body, because Good American jeans are cut for women with a big ratio/difference between the waist and the hips. They have defined waists and fuller, curvier hips and bum, or what I refer to as a Style Dial Orange. This is not my body type, and no amount of money spent on jeans is going to give me those curves.

So always remember: It’s not you, it’s the __(iinsert item here)________________ that you are trying on, that’s flawed.

I’m not naming names, but you know the brand I’m talking about, and it is not Chanel. Printed quilted fabric bags are one of a handful of aging accessories that I advise staying away from. Not only are they not very chic, but they are also limiting because the patterns are so bold and not very versatile.

Also avoid: Boring strictly utilitarian bags with lots of outside pockets. Instead, choose a classic leather or faux leather bag in a structured shape (easier to dress up or down) and medium size that is close to the color of your hair, or your favorite dark neutral. This is an investment piece that will complement nearly every outfit for years to come.

Minimal outfits without color, pattern, or shine can be very chic and look very contemporary, and they are the most straightforward path to a stylish and modern look. The key to pulling off a minimal look, however, is great fit and details, because the fewer the details, the more significant each one becomes.

If, however, minimalism is not your thing, or your basic pieces don’t feel exciting or interesting enough to stand on their own, then transform your outfit from boring to beautiful by adding accessories or completer pieces in either a color, a pattern, or a shine.

One tip is to ask yourself what’s missing from the outfit, and add that missing element with an accessory. For example, if the outfit is all neutral, a pop of color (in only one piece, not several) is an easy and fun way to add interest.

Years ago, when I was a budding dancer at the Winchester School of Dance, Mrs. Winchester used to warn us against pointing out our own mistakes. “When you mess up,” she would say, “just keep dancing. Don’t stop, stare at the audience, and say ‘I made a mistake, I made a mistake.'” I’ve never forgotten that advice.

Nobody is perfect. Except for Kate Middleton. But seriously, nobody. We all have areas of our faces and bodies that we would rather not draw attention to, but we often don’t realize we are doing it. If you have a full tummy, a shirt hem that ends at the fullest part, or a contrasting waistband, or a belt, can all draw the eye to that feature. Bright nail polish can draw attention to aging hands. A choker can often highlight a less than smooth neck. If you are comfortable with these parts of your body, then by all means, flaunt them, but if you’re looking to downplay something, don’t use details (such as hems, colors, or embellishments) to draw attention to it.

The vast majority of women who struggle with that nothing-to-wear feeling are missing the wardrobe essentials that I talk about all the time. These essentials should comprise about 70-80% of your wardrobe. The remaining pieces can be the fun, trendy, statement pieces (these used to be called costume pieces). Without the essential pieces, you will not have the versatile, mix-and-match wardrobe of your dreams.

I’ve come up with my own version of these essentials, categorized into catalogs by decade (40s, 50s, 60s, etc.), with oodles of outfit ideas. And you can find them, for free, right here.

Don’t set yourself up for a closet full of compromises. When we shop under duress (in a hurry, for a specific last-minute event) we tend to settle for items that are merely passable. Year after year of compromising in a store yields a wardrobe that is jam-packed full of ho-hum clothes.

Hold yourself, and your wardrobe, to a higher standard, by only buying pieces that check all of your boxes.

Many of the outfits we admire on social media consist of the essentials (see above) plus thoughtfully chosen accessories that reflect your personal style. These can be sleek and simple or fun and fabulous. It’s up to you and your personal style. If you are lost in your style right now and don’t know where to start, remember this simple formula:

Wardrobe Essentials + Beautiful Accessories = Chic Outfits

It’s that simple. Start with the essentials, add interest and personality with accessories, and you’ll have a chic and effortless look.

A cluster is a concept that I’ve developed and perfected over the years, and it makes building a wardrobe simple and straightforward. You simply start with 6 pieces.

A cluster is essentially a 6-piece mini capsule.

Cluster = 3 tops + 2 bottoms + 1 jacket

If all of these pieces mix and match together, you will have 12 outfits. This is easily enough to start a new wardrobe from scratch (switching jobs or lifestyles or zip codes, losing or gaining weight), pack for a trip, or update your wardrobe for the season. Just start with those 6 pieces. Make sure they all go together. And use it as a building block for your wardrobe. Add another cluster, and you will have up to 36 outfits.

As you can see, it’s kind of magical.

I hope you enjoyed this roundup of some of my best style tips and advice! Which tip was your favorite? Let me know in the comments!