Woman with brown hair wearing a leather jacket and sunglasses looking at the camera

How to dress your age

Jun 22, 2021

In 2021, what does this statement even mean? What about “How to act your age”?! I think I like that one better.

I get the question about what is appropriate so often, and each time it reminds me that we are truly pioneers in fashion! We most likely don’t dress the way our mothers did at our age, so we have no historical reference point. I would love to dress like Grace Kelly every day or even Jane Birkin (the girl the Hermès Birkin bag is named after), but that is obviously out of the question. The world is so different now – things are much more casual but polished. We are active much longer, and we are living longer. We may be working well into our 70s if we so choose! **At the bottom of this post, you’ll find a shoppable selection of some items great for women 40 and over.

My response, when people ask me to teach them how to “dress appropriately for their age”, is that we need to look deeper into it than that. It has to do with your current lifestyle, any body issues you may feel you have, and what age you FEEL, not so much the age that you are biologically. That being said, I probably wouldn’t recommend a micro mini skirt, but you can wear short skirts with tights and/or tall boots for example.

For most of us, gravity has reshaped things a little, and therefore, we need to be careful about wearing super clingy fabrics. No one needs to leave her house without looking at herself in the mirror from all angles, especially from the BACK. If you can’t manage this, ask someone to help. They can take a quick photo and show you. Another tip is to sit down in a chair in front of a full length mirror, and look at yourself from the front and from the side. It’s really smart to do this in the dressing room at a store if possible, before you even purchase the item.

If there are pieces that you are wondering about, that’s probably the answer to your question. You will never feel totally comfortable wearing that item if you are questioning it to begin with. No amount of talking you into it, or someone telling you it looks great, will convince you otherwise. Instead, think of new ways to wear the garment if it’s a piece you adore but aren’t sure about any more.

If it is a much loved leather motorcycle jacket, for example; instead of pairing it with distressed jeans and a graphic tee (a graphic tee is a classic band tee for example; an old T-shirt from a Rolling Stones concert, or a new T-shirt pretending to be an old T-shirt from a Rolling Stones concert!), you can instead pair it with a simple dress and strappy sandal. Throw the jacket over your shoulders (“Vogue editor” style) and you’re instantly sophisticated and chic- that’s ageless style to me.

If you still love a good distressed jean, pair it with something more polished- a silk blouse or blazer.

Jumpsuits are a great day into night look with a little more coverage.

Look for dresses with ruching, super flattering for the tummy area!

Another thing to keep in mind is the importance of undergarments. The most important of which is probably your bra. I know it’s difficult to find anyone who actually measures you in a store anymore, but whenever possible it is better to find at least the first bra in person in a store, and be prepared to try on many, many options before you find the right one for you. It will be a pain, I’m not going to lie to you, but it is one day, and after that you can order them from home! You can get them in nude and black, and find a strapless version as well, unless strapless bras don’t work for you, and you are all set. This is one piece that you need to be prepared to spend a little money on, it is really the ultimate investment piece. Your clothes can look entirely different simply based on what is underneath.

Also, this may seem like a no-brainer, but when you are young, you can get away with wrinkled clothes, wet hair etc. If you want to feel polished and put together as an adult, you need to take a little more time with your clothes, the ones that are already in your closet. If you fold certain tops rather than hanging them for example, you need to take them out the day before and give them a steam and hang them to dry. I’ve said this many times before, but if you steam a garment, and then wear it out the door 10 minutes later, it will become even more wrinkled.

All any of this takes is a little bit more time spent on yourself, but you’re certainly worth it!

One last suggestion, look for stylish shoes that are comfortable, not comfort shoes. Does that make sense? Big, clunky shoes add a heaviness to your look, and draw the eye down to the foot. You do not need high heels, just stylish options that you are excited to wear. There are plenty of attractive shoes out there!

What age do you feel? Are you dressing in a way that is authentic to that? Do your clothes tell the world something about who you are are? If your answer is “yes”, then you are on the right path!

Below you’ll find some shoppable items great for women who are 40 and older!

Alison Bruhn




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