InStyle’s Fashion Director Cindy Weber Cleary has been a fashion editor for the past 20+ years. Needless to say, she’s picked up some tricks along the way. Catch her column here each week for how-to tips and style secrets on her favorite, timeless styles. This week, we gave readers the chance to ask Cindy style questions on Facebook. Here, Cindy responds to one lucky reader. Head over to our Facebook page and a submit an idea for Cindy’s next column!

Q. “Hi, Cindy, do you have any suggestions for a 54 year old working woman who just wants to update her closet? I am not sure what items would be my best investments. Thanks.”—Elizabeth Saldivar

A. Hi, Elizabeth, thank you for your question. It’s a good one! I would say the top 3 investments for a working woman should be: a versatile dress, a coat to the knee or longer, and a satchel or medium sized shoulder bag.

The Dress
When my staff and I were previewing the Fall collections, we kept coming across what we called a “forever dress”. What defines a forever dress is a timeless silhouette in a length that is neither too short nor too long made in a fine fabric with elegant finishing details, like the Jason Wu, Carolina Herrera, and Ralph Lauren dresses above. They tend to be expensive, but when you factor in how often you will wear them and for how many years, they begin to look like a bargain! Think of buying one as a long-term investment and go for the best quality that you can afford.

You should note that these dresses are in solid, fairly neutral colors with no prints or flashy details. At first glance, they may even seem basic. What’s great about them is that you can easily update them from season to season with a change accessories and you can dress them up or down for any number of occasions ranging from a business meeting to a cocktail party.

I realize that many women can’t afford to buy clothes from the world’s top designers, so here is a range of relatively affordable versions of the forever dress:

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From left: Veronica Beard, $550, veronicabeard.com; Goat, $835, matchesfashion.com; COS, $125, cosstores.com

The Coat
The weight of the coat will depend on where you live and the climate. It should reach right below your knee or slightly longer, so you can wear it over a variety of underpinnings. Ideally, you should be able to wear it over cocktail attire as well as day wear. Classic shapes such as a trench, a robe coat, and a menswear-inspired topcoat all fit the bill, but it’s okay to go for something with a bit more flare, such as a funnel neck, a zipper detail or leather trim. If it’s your only work coat, I would suggest a neutral color, such as charcoal, camel, navy, olive, stone, or black. Since you will wear a coat more than any other garment in the winter, buy the best quality you can afford.

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From left: Sportmax, $1,017, matchesfashion.com; Issa, $725, net-a-porter.com; Vince, $725, matchesfashion.com

The Bag
A satchel or shoulder bag are your best bets. It should be big enough to hold a mini-umbrella and a pair of flats as well as you wallet, phone, glasses, etc, but not huge. If you want a beautiful bag that you will carry for years, you might want to skip anything that constitutes an “it bag,” as they have a relatively short shelf life. They are too identifiable. Neutral colors such as grey, olive, navy, and wine are versatile and can be more interesting than basic black, but everyone should have at least one chic black bag. Once again, consider how often you will carry the bag. If it’s almost everyday you go to work, it’s worth buying one that’s beautifully made and will last for years.

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From left: Elizabeth and James, $545, nordstrom.com; 3.1 Phillip Lim, $750, saksfifthavenue.com; Jason Wu, $2,395, neimanmarcus.com