Retirement Style: How to Look Stylish After Retirement

retirement style

For years, women have been asking me to write a blog about retirement style.  Up until now I haven’t done it.  It’s not that I didn’t want to, the topic just seemed like such a huge one to tackle.  With Baby Boomers now hitting retirement age, we all know that this generation is one with a loud voice who won’t go sweetly into the night.  This is a group that has always questioned the status quo and, not surprisingly, are doing it again as they prepare for their “third acts”, as Jane Fonda would say.  How do I, someone who is decades away from retirement, try to distill retirement style down one blog post in a way that doesn’t condescend to a group of people with way more mileage on their odometers than I have?  Like I can tell someone who has lived longer than me how to dress.

Then I realized I was over thinking this.

While I may not be of retirement age, I certainly have dressed my fair share of women who are or will be entering this phase of life soon.  And I have certainly given dressing tips on this blog about things I personally know nothing about before, like mom and pregnancy style.

Yet this still seemed tricky .  Being a lover of the Netflix series Grace and Frankie, starring Jane Fonda and Lily Tomlin, it’s all too clear to me that retirement style isn’t cookie cutter.  In fact, this show actually manages to make getting older seem cool.  You have two women with diametrically opposed life views, with personal styles that match these views, and you realize, there is no one way to dress after you have started living off your IRA, Social Security, 401K, and/ or pension.   However, despite how different one retiree does life in comparison to another, there are still some core similarities in dressing that I want to address in today’s post on retirement style.

Do you, you’ve earned it

When I think about living in my retirement years, I see myself just letting it all hang loose.  I think of a blog like Advanced Style, and think, “Yes! This will be me!”  The idea of answering to nobody, having no other style agenda than to just be me feels so liberating.  Sure, you’re never to young to embrace this in theory, but when you reach a certain age I think you have earned the right to decide that you have lived too long to need to explain anything to anyone.  Screw it!  Right?

A book I love is Wacky Chicks by Simon Doonan.  A friend of mine gave it to me years ago and I was honored that someone would think of me in reference to a book about non-conformist women who dare to be different.   I think this is such a key to retirement style, being a non-conformist, to finally embrace the essence of what makes you unique and to stop worrying so much about what other people think.  If not by retirement, then when, I ask you?  So do you, you’ve earned it.

Retirement Style Inspiration

retirement style

You don’t have to look far to notice that there is no one way to do retirement style.  Comparing a style icon like Iris Apfel, an award winning actress like Helen Mirren and recording artist Tina Turner, for example, it proves there isn’t an easy map to follow when dressing in your later years.  Liberating for some and daunting for others, I’m sure.  After all, sometimes rules can be helpful.  Women seem to want a “do this, don’t do that” map for style to make sure they are doing it right.  But doesn’t that seem sort of boring and restrictive?

Why not try dressing authentically?  Despite the differences in style of the three women I cited above, what they all share is style authenticity. This, I think, is the goal.

So what is your authentic retirement style?  Unfortunately, I can’t answer that for you.  However, I believe you don’t have to look far to find it.  As you transition from one phase of your life to another, there is nothing that says that you have to abandon the style you always had and enjoyed.  Sure, you may evolve it, but assuming that you have to bid farewell to a look you always loved is a falsehood.   Long gone is the idea that retired women shop for cheap polyester pull on pants and cut their short because they say old women shouldn’t have long hair.

Dressing young and dressing youthful are two different things

Whenever I work with a client who is either in or reaching retirement and they explain to me they don’t want to look young, they just want to look age appropriately stylish, I always tell them that dressing young and dressing youthful are two different things.  Dressing young often gives off a vibe that a woman is resisting her age and dressing youthful sends the message that she accepts her age and honors the essence of who she is.  Yet, it’s not just what a woman wears in her later years that makes a difference, it’s how she wears it that does.

I once rode an elevator with famed costume designer and stylist Patricia Fields.  She happens to live in the same building as a client of mine.  Instead of gushing over meeting her, I pretended I didn’t know who she was and I used the time to really look at her, a woman who is in her 70’s with pink dyed hair who was wearing a pair of Vans with skulls printed on them.  Nothing about the fact that she is a senior citizen with pink hair seemed at all out of place…for her.  It was honest, authentic and I’d expect nothing different.   However, if we were to compare this to a woman who was petrified of getting older and decided to dye her hair pink to try to stay relevant then I think it would be easy to sniff out the inauthenticity quite easily.  Dressing youthfully doesn’t mean to turn your back on irreverent or silly things that one made you happy, or to declare yourself too old to wear something once enjoyed.  It’s about honoring yourself and learning how to embrace that essence at this new stage in your life.

Evolving Your Style for Retirement

So let’s talk about you.  What do you want to do in retirement?  What do you value?  How will you want to spend your time?  How do you want to live?    Will you be spending time with your grandchildren?  Do you have plans for travel?  Do you plan on volunteering or sitting on boards in your former profession?  Most importantly, what did you dislike when you didn’t have so much freedom to come and go as you pleased and dressed how you wanted?  What clothing items would you toss on a huge bonfire because you won’t have to wear them ever again?  These are all questions you need to consider when evolving your style for retirement.

Regardless of how you will be spending your time, it is likely your retirement style will be much more casual than when you worked.  The goal is to morph what once was into what what is.  Even if you plan on spending time volunteering or attending dressier events, these engagements will likely be a lot less frequent.  A smart idea would be to divide your time into percentages and look at the amount you will be doing each thing and create a wardrobe according to the time spent partaking in each activity.  The more you plan on doing it, the more you clothing options you need, and vice versa.  Let’s create a profile of a woman in retirement to show how you can do this.

Let’s say this pretend retired woman plans on traveling twice a year abroad and domestically for a few weeks at a time.  She has family spread all over the country and will either have family visiting her or she will be visiting them.  She enjoys tennis with her husband a few days a week, tries to get to the gym at least four times a week, has date nights on Fridays with her husband and still has a group of women she tries to see monthly for a girls’ night out.  She volunteers her time at an adult literacy program because she was a teacher before retiring and needs to attend at least one formal function a year because of her husband’s former profession.

If this client came to me, my plan would be to make the majority of her wardrobe smart casual and fill it with easy pieces that she can dress up and down.  I’d make sure she has a decent amount of well fitting pants, a good pair of jeans, some basic tops, like tunics, fun blouses and sweaters that can be dressed up and down, maybe one blazer, several cardigans and a lot of scarves and shoe choices so she could change these basis core outfits to go from one part of her life to the next.  I would then make sure she always has one good dress that she could wear to events she gets invited to that is basic enough to accessorize different ways.  I’d make sure most of her wardrobe packs and travels well, is easy care for and comfortable.  To keep her style feeling relevant and up to date, I would focus on keeping the trends to the accessories, like her shoes, jewelry, bags and scarves.

Write down your retirement plan and look at how often you will be engaging in each thing and decide.  If you want more info on creating this type of breakdown, you can read this post here.

Dressing the retirement body

We’d have to eventually talk about dressing your body because, as you probably know better than I do, your body has changed.  In addition to this, you may be dealing with some pain or problems simply due to normal wear and tear.  Your waist isn’t as slim in the middle, your boobs aren’t perky, your butt not as lifted, and so on.  Even sadder is the fact that older women are woefully underserved when it comes to clothing.  Yet, over the course of doing my job, I have encountered many labels I really like and think keep this woman in mind.  Some of these brands I also like for younger clients too.  I just have that found these labels tend to be a bit more conscientious about the fact that all women are not 25 years old and many will cut their clothing accordingly.

Mid-price brands

Higher-price bands

Do you have a brand you love? I would love hear about them!

Retirement style outfits

Lastly, I’d be remiss if didn’t include a few retirement style looks, if anything to show how different all the looks can be.  Check them out below, along with some additional tips on dressing for your third act.

Outfit #1

retirement style

I came up with this retirement style look when I thought about a woman like Helen Mirren or Jane Fonda, who often prefer chic, crisp looks.  I envisioned this type of outfit for a woman who volunteers, attends daytime events or has dressy casual needs.  What works about this look is the fit.  Not only is the outfit appropriate but the fit caters to a woman with a more advanced body shape.  The top is by Lafayette 148.  It has a side zip and ruched front while also framing the face and neck beautifully.  Many of my clients have purchased it and it is stunning.  The pants are from Chico’s and these pants address the skinny pants trend in a realistic manner.

Finishing the look, I added this Lagos necklace.  In many cases, retirement aged women have spent years building their jewelry collection and often have investment pieces on hand.  Don’t pack them away, dress up your more casual looks using them.  For the shoes, I chose these Bottega Veneta flats in burgundy, because the need for flats will likely outweigh the need for heels, and the taupe bag is by Aquatalia.

Outfit #2

retirement style

This next retirement style look is for more casual days.  I think it’s important to have laid back pieces in your closet that have polish and finish considering you’ll likely be spending your time in a casual manner but don’t want to look sloppy.  I styled this Eileen Fisher tank and cardigan with a pair of Piazza Sempione pants.  I’m not a huge fan of all of Piazza Sempione’s clothing, but their pants are amazing.  I particularly love the Audrey style I featured above.  I chose the matching tank and cardigan to create a lean monochromatic look which can be very flattering.

With such a classic base, you can mix and match different accessories to dress up and dress down the outfits.  In the look above, I used these hot pink Sam Edelman sandals, a colorful necklace in pink and tangerine and olive bag from olive crossbody bag from Nordstrom.

Outfit #3

retirement style

This last look I styled using a tunic top from Lands’ End.  I chose a tunic because I think it is a worthy staple for women in retirement.  These types of tops don’t require a lot of fuss or layering to look finished and the shape is easy for most to wear.  I styled this tunic with a pair of fitted cigarette pants from Nic and Zoe, flat booties from Marc Fisher and added some pops of color with this yellow crossbody from Loewe, printed silk scarf from Nordstrom, Melissa Joy Manning pearl earrings and beaded bangle from House of Harlow.

Color near the face is quite often flattering after reaching a certain age.  It brightens the skin.  To make skin also look refreshed, very shiny fabrics are often reflective and can emphasize wrinkles whereas matte fabrics and textures tend to minimize them.

Additionally, if you notice, the clothing pieces are on the basic side and the trends are found in the accessories.  This is one way to keep your wardrobe age appropriately updated.

If you are preparing for retirement or already settled in to this phase of your life, I hope these tips help you.  I would also love to hear from you.  What do you think are some important dressing tips to keep in mind when styling yourself after retirement?




  • Barbara

    Thank you! The list of brands is exactly what I needed to see….I will have some fun checking them out! I retired from an office job (engineering) 4 years ago and now spend most of my time at home on my small farm. Big change in type of clothing necessary! Farm wear is not really very stylish…but I don’t want to give up on looking good either! So my dilemna is finding cool, stylish clothing that is appropriate for outdoor work with horses yet not so expensive that I won’t wear it for fear of ruining it. Oh, and is also age appropriate 🙂
    Thanks for always providing interesting reading, I check out your blog every day, love it!

    • Wow! That sounds like a great way to spend retirement time! I would definitely give Karen Kane a look. I find her stuff to be really relaxed but quite stylish and very comfortable. Her faux suede leggings are heaven and her tops are super comfortable. Have you also considered having clothing specifically for outdoor work, as I would imagine you get quite messy, and then a few key pieces for non-outdoor stuff? I have a client in Montana who lives on a cattle ranch and she definitely separates the two.

    • Oh J. Jill too. My mom LOVES her J. Jill. I also think Nic and Zoe can be nice for slightly elevated looks given your lifestyle.

  • Megan

    Wow! Like Barbara, I’m recently retired & spend most of my time in a rural farm environment (my Border Collie & I herd sheep.) I’ve been surprised that the fashion blogs I gravitate to tend to feature more urban style, but I think I like them because the clothes are simple, classic, & tailored. But I usually wear jeans & boots & turquoise. So, I’ve felt confused about conflicting styles, but I’m beginning to realize I can mix them–some streamlined & some boho/cowgirl/country.

    • Oh I think mixing that would be really fabulous. Add a bit of flavor to your more rural looks. I think that is a great way to infuse a little you into these more relaxed styles. I can totally see you rocking some turquoise jewelry with it!

  • Cynthia Peterson

    I’ve been retired for 8 years now after teaching for 38 years. I find I have much more of a uniform now than I ever did when I was teaching. My look is similar to your #3, although in addition to plain tunics I also wear interesting tops with basic skinny pants. I add more accessories depending on the amount of decoration on top. I have always loved fashion but am much more relaxed and confident about it now. My favorite shoes are my calf hair leopard booties!

    • You totally nailed it! I think that is right on and how most women do it. I think it is all about making enough of a statement without going over the top because it just isn’t necessary. I LOVE the idea of the leopard booties! They can go a very long way towards making a more subtle outfit look exciting!

  • Patricia

    My LIfe :I go to the gym four or five days a week. I meet friends for a walk or a movie/lunch. I go to theater with my husband probably twice a month. We usually travel overseas twice a year. We usually attend a few parties every holiday season. Our own entertainment tends to be dinner parties or back yard barbeques. I babysit the grandkids for three days at a time and do activities with them.

    My Look: I’ve been retired for awhile now and I think I’ve found a look that fits me at this stage. I typically wear pants with knit tops or sweaters with flats or ankle boots. On dry days (live in Seattle) I’ll wear a stylish casual jacket like jeans jacket or cropped wool jacket. Since I spend a lot of time wearing coats in fall/winter, I spent a long time looking for the right one to replace my old beloved coat. It had to have a hood and be simple in style with a few chic details. I just ordered the Sam Edelman Chelsea ankle rain boots. I wear scarves as my go-to accessory and recently added a few pair of colorful flats.

    My Issues: I spend far too much of my time wearing Sketchers go-walk flats. They’re so darn comfy and fabulous for travel and spending hours and hours walking, but not all that stylish in appearance. Trying to wean myself away.I don’t wear prints often, mostly solid colors. When I do wear them, I get compliments … I may need to add a few prints as I replace tops in the future.

    Right now I’m not shopping. I just finished a giant weed-out and have sent a lot to consignment, vintage, charity and friends. I’m in no hurry to cram more stuff in my carefully edited closet.
    You’ve given me a few things to think about … always a sign of a good post.

    • Christine Binnendyk

      Thanks Patricia — I’m going to hunt down those ankle rain boots!

    • Great stuff, Patricia! You really seem to have a good handle on your needs. Regarding a replacement for those Sketchers, have you checked out the Melanie Flat by Frye. They’re not cheap but EVERYONE has been buying them and they are SO comfortable-

      The most popular color has been the taupe, but a few clients have bought the cognac and the gold. You can also check out my post on Sabrinas flats. Normally I wouldn’t consider ballerina flats good walking shoes but these are pretty amazing and I would wear them as such.

      • Patricia

        I pinned the Melanie Flat for future reference. When I replace a pair of shoes, I’ll try these. I have three pair of ballet style flats (with small heels) so would probably rule out the Sabrinas for now.
        Good to hear about the Tinsley rain boot. I ordered mine online and haven’t actually tried them on yet. I go them from Nordstroms so it they’re not great, I can take them right back.. Fun post.

  • Charlene

    I first found your blog a few years back when I was looking for help with my retirement wardrobe. Your post on dressing “youthful vs. young” was terrific and I have been a fan ever since. With your advice, I have added a denim skirt, cognac boots, skinny jeans, leggings (bum carefully covered) and a tan purse to my wardrobe. I’ve learned about proportion, layers, and silhouettes. So, dear Bridgette, you have been helping this retired gal all along! Thank you and keep up the good work!
    Charlene H.

    • Hi Charlene! You are too kind! Thanks for being a longtime reader. I really appreciate that! I am glad you have been learning about retirement style this whole time. Your clothing and accessories choices sound perfect!

  • Pat

    Bravissimo, Bridgette! Your knowledge and expertise is timeless and ageless…that’s why we love you!! Clearly, some of your fans have been waiting a long time for this ( myself included). Thank you for sharing so generously…also, I love your longer hair style…
    a faithful fan,

    • Thank you Pat! I know you were the one who was asking for this so I am glad to hear you are pleased!!

  • Hope Springs

    I just discovered your blog and this post is really timely for me, and I’ve also enjoyed the discussion below. Since I’m recently retired, I absolutely love the post you linked to with the pie chart/time spent and the question “where will you wear this?” I initially found it hard to pass up clothes I loved although I no longer have anywhere to wear them. Purging my closet of things I don’t need anymore has really opened my eyes to that fact. I even gave away my lucky interview jacket. 😉 Great blog! I look forward to reading backward into the archives.

    • Hi! Thank you for such kind words about my blog and this post! I appreciate your comment and your interest in reading more! Thanks!

  • First, I want to say this post is excellent. There is only one thing I don’t like and it’s the phrase “age appropriate”, I’d like to see that phrase disappear. It is so offensive to women over fifty. Did you know that if you google the phrase “Age Appropriate” you will come across what is age appropriate for children and teens? “Age Appropriate” started as a phrase long ago when determining what was considered too sexual or grown up for children/teens to wear and also what types of toys to play with, movies too watch etc. And somewhere along the line it drifted away from that meaning and became a phrase to shame older women for their clothing choices. I also find it’s older women shaming other older women with that phrase. I don’t see young people use that phrase as often.

    That being said, I want to say that I love, absolutely love, everything else you said, plus all your outfit choices. I will be pinning them all. BUT, here is my problem…they are all unaffordable for the average senior citizen. I can not afford to shop at Chicos or Talbots. I clicked on the picture of that white top in the first picture because I loved it, but when I saw the price I just about gasped. That is price is half of my husband’s paycheck after taxes. Most seniors are on a fixed income. The fashion industry seems to think that if your older, you have money. And a lot of seniors do. But even more do not. They are on a fixed income struggling with paying bills. I really wish someone would create a Forever21 for my age group. We want to look nice. We want clothes that fit are changing bodies. But we can’t afford to pay $100 for a top or a pair of jeans. We can’t.

  • Cheryl

    How timely this blog post is for me. I turned 54 a few weeks ago and Thursday is my last day of work. I had planned to retire next year but a change in structure allowed me to leave earlier. I have been dressing very casually for the last year (our office moved) so don’t expect my wardrobe to shift a lot but I do want to keep current as I move into this new phase of my life. The lifestyle you described fits to a T. I plan to spend a few months on a beach and do a few other shorter trips, will do some volunteer work, spend time at the gym, and attend one or two formal events per year. The simple clean style of Helen Mirren resonates with me as do the outfits you chose. Thanks very much.

    • Well happy belated birthday and happiest of retirements! It sounds like you will be spending your retirement having a lot of fun!! I think women of all ages find Helen Mirren inspiring! I am glad you do too! Enjoy!