Let’s get real. Do you really want to build a sustainable wardrobe that you can enjoy for years? Or are you satisfied with buying new clothes every season, not only because they feel fresh and current but because last year’s wardrobe now feels worn out, lackluster and boring? Personally, I’m quite serious about having a closet comprised of timeless essentials that also feel fashionable and beautiful. I want to wear my clothes for years, not just months.
But I also want them to help me create interesting and current outfits that express my personal style and suit my real lifestyle. I’ve discovered that takes time, intention and investment. So today I’m sharing part one of a two-part series on timeless wardrobe investments you’ll wear for years. Build your wardrobe with these in mind, and you’ll have a sustainable, high-quality assortment of garments that will be some of the best investments you’ve ever made.
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Since I started blogging here at Dressed for My Day in March, 2018, I’ve met so many amazing women who tell me that I’ve helped them reestablish their sense of style and curate a wardrobe they enjoy wearing. When I began blogging, I had just turned 54, my kids had left the nest, I was teetering on menopause (and feeling all the symptoms, including hair loss) and I had finally lost 20 stubborn perimenopausal pounds. Within a few months of starting this new endeavor, my husband and I also endured a major loss and career change and eventually a move. So I understand the extreme changes women over 50 go through that sometimes cause us to feel like we’ve lost our way…and our sense of style.
My goal here at Dressed for My Day has always been two-fold. First it has served as an impetus for me to get dressed for MY day. Yes, I struggle with that some days, too. But my motivating goal for this blog and my YouTube channel has been to help other women like myself to sort through the confusion and loss and doubts we encounter in midlife so we can again establish ourselves as smart, well-informed, beautifully presentable and confident contributors to our world. And in my book that means we need to get savvy about dressing our unique bodies, defining our personal styles and building wardrobes that really works for us. (You can click through the links in the previous sentence to check out the style series I’ve created around each of those topics.)
Part of dressing smart as a woman over 50 also includes leaning into a well-curated wardrobe that gives you flexibility for your varying lifestyle, is sustainable and long-lasting and frees you up from the whims of fashion trends and shifts. I discovered years ago that it’s smart to be aware of the fashion trends, especially those that have to do with silhouettes and lengths. But as a seasoned woman I can end up looking silly and immature if I chase the all of the trends, constantly changing my personal style to revolve around these elusive fashion fantasies.
So for the past several years I have been intentionally building a closet full of timeless wardrobe investments that I know will serve me well for years to come. Indeed, I’ve had some of these items for over six years now, and I still wear them just as frequently as I did when they first entered my closet.
I’m frequently asked what items are worth investing a little more in and which should we spend less on. Honestly, I think the answers to those questions will vary for different women. Depending on your lifestyle and personal style preferences, you may not want to invest in all six of the timeless wardrobe investments I’m detailing here. But these are definitely worth considering, especially if you gravitate to classic styling and you want to build a wardrobe that works together to produce multiple outfits.
One more important thing before I run through my list. I’m not sharing this list today in order to compel you to buy all of these items immediately. In my estimation, these are the worthwhile purchases that you make slowly and thoughtfully. Some have said that when we shop we either hunt or gather. We gather when we shop recreationally and purchase things as we find them. But we hunt when we do a little research, think about it, maybe even pray about it, and then set out to find an item. I recommend you hunt for these deliberately, strategically and thoughtfully. My list is simply meant to be a starting place.
Timeless Wardrobe Investment: Classic Button-Up Shirt
A classic button-up shirt is a four-season staple. While many of us may have thought of this structured shirt as a workwear essential before, it has definitely transitioned to a multi-use basic that can contribute to both office-ready and more relaxed outfits.
The Citizens of Humanity Kayla shirt above is my absolute favorite one in my closet and I’ve had it about three years now. I like it because the fit is generous and modern, but the details are classic. And discreet buttons along the outside of the sleeves enable you to roll up or cuff the sleeves easily for a more relaxed look, which is usually my desire.
You can wear button-up shirts tucked or untucked, alone, with a jacket, under a cardigan or even under a jumper (if they come back into style one of these days…and they undoubtedly will!). They also double as swimsuit coverups and jackets over tank tops, summer dresses and tees. You’ll be amazed at the versatility once you finally invest in one and prod yourself to wear it.
For a more classic, slim fit, I really like the Brochu Walker Everyday shirt. This shirt is constructed in substantial 65% Polyester/35% Cotton fabric for a silky soft feel with some stretch. It especially looks sharp under a jacket or cardigan for a more polished look.
I think it’s smart to invest in at least one button-up shirt you truly feel comfortable in, that fits your real lifestyle and that you can enjoy wearing with other things in your closet. But if you’re not one to wear this style frequently, you may want to invest less but still get a good shirt. I recommend the popular Lands’ End Cooling button up shirt shown above. It’s substantial, but also comfortable. I’m wearing my true size medium above for a classic, slim fit that works nicely with a blazer or other topper.
But if you plan to wear this classic shirt more frequently by itself and casually, you might want to size up for a more oversized fit. I’ve gathered other button-up shirts that I think are worth the investment in the shopping widget below. And you might want to check out my post 8 of the Best White Button-Front Shirts for Women for my evaluations.
Let me know in the comments if you agree that a white button-up shirt is a worthy investment. I do know that some women prefer not to wear them or feel they don’t suit their style. So if you don’t add this essential to your closet, what do you substitute? I’d love to hear from you.
Timeless Wardrobe Investment: Cashmere Crewneck or V-Neck Sweater
Another worthy investment for your closet is a cashmere crewneck or V-neck sweater. Even if you live in a warmer climate, this classic piece can provide versatility and stretch your wardrobe.
You can wear a cashmere sweater three seasons in most climates. And I always travel with one, usually this one in oatmeal because it’s so versatile. I do love a good neutral colored cashmere. But don’t hesitate to invest in cashmere sweaters in beautiful, striking colors, too.
Remember, colors do not go out of style. Yes, some colors will be more “on trend” than others each year. But all that really means is that those colors will be plentiful in the stores. You can wear absolutely any color that makes you look radiant and you’ll look stylish and on point. That’s why you don’t need to limit your timeless cashmere investment to a neutral. I’ve gathered several of my favorite cashmere sweaters worth the investment in the shopping widget below.
Do you agree that a cashmere sweater is a timeless wardrobe investment? Or do you prefer cotton or some other fabrication? I do think it’s smart to have a couple of good cotton sweaters in your wardrobe as well, especially for spring and fall. And they come in handy during the summer, too. Let me know your thoughts below in the comments.
Timeless Wardrobe Investment: Full Length Straight Leg Jeans
Each year denim trends change slightly. And about every 8-10 years we see a major shift in the jeans we’re wearing. I think most of us have finally transitioned from the skinny jeans we wore for years, but now barrel jeans are causing another conundrum. Ha!
While wide leg jeans and bootcut jeans are also fairly safe options for staying current through the years, you’ll never go wrong with a pair of classic straight leg jeans. The Mother the Kick It straight leg jeans shown above are probably my absolute favorite jeans that I wear most frequently. And I always reach for these when I want a very timeless look. Yes, I do have a raw hemline, but that’s because I cut them off. The Mother the Kick It straight leg jeans actually comes in a hem.
I give these Mother the Kick It straight leg jeans a “classic stamp of approval” because they’re a medium wash, they have no distressing and only minimal, stylish whiskering, and they’re a classic straight leg with a high rise, which I personally enjoy. But look for the straight leg jeans that fit your lifestyle and your body shape and proportions. I think it’s smart to add this timeless wardrobe investment to your closet because it’s the jean you can wear anytime you want to look classic, and it’s also easy to pair with the shoes in your closet.
Do you think it’s smart to have a pair of straight leg jeans in your closet? You might want to check out my recent video on how to pair your shoes with your outfits. You’ll see there that straight leg jeans make getting dressed so easy!
Timeless Wardrobe Investment: Double Faced Wool Blend Coat
Outerwear is important not only because it keeps us warm and protected from the elements, but also because it’s the first thing people see of us when we wear it. First impressions are lasting impressions, and they’re hard to change. So showing up in a beautiful coat that completes your outfit is worth the investment.
If you’re going to invest in a coat that you’ll wear for years (and potentially even pass on to a daughter or granddaughter) I suggest a double-face wool coat.
A double-face wool coat is a high-end, often hand-finished garment made from two layers of fabric woven together to create a single, often reversible and unlined piece with finished surfaces on both sides. These coats feel and look a little more luxurious and they hold their value beautifully. If you can score one at a second hand shop, you’ve found treasure.
Coats are on their way out seasonally right now, so they’re not especially easy to find. But if you find a good double-face wool coat on sale in your size, now is the time to nab it. I’ve collected some of my favorites that are available in limited sizes below.
Timeless Wardrobe Investment: Trench Coat
I shared ad nauseum about the virtues of the trench coat in yesterday’s blog post. So I won’t go into all of the details about why I think it’s a worthwhile investment. But let’s at least hit the high points.
A classic trench coat will add structure to any outfit you wear. So even if you’re wearing jeans or more casual pants, the addition of this iconic coat will elevate your look. You’ll always look polished and smart in a trench coat.
Of course, it’s also great for protection from the elements, especially on a spring or fall day. And I like to travel with one, too. I’ve collected some of my favorites in the shopping widget below. And right now is definitely the time to add one to your closet for spring.
Timeless Wardrobe Investment: Blazer
Finally, I think a smart blazer is a timeless wardrobe investment you can enjoy for years. If you’ve recently transitioned out of the workforce and these menswear inspired jackets were part of your daily looks, I encourage you to choose a favorite or two and hold onto them. You may be tired of wearing them, but now is the time to give those jackets a different spin.
Yes, you can wear a blazer with coordinating pants, as I’m doing above. But you can also create a more relaxed, casual outfit with blazers these days. Above and below I’m wearing the same iconic Veronica Beard Miller Dickey Jacket, but in very different ways. Oh, and how do I love this blazer? Let me count the ways! I’ve been wearing this one for about five years and I’m still excited every time I put it on.
I love this double-breasted blazer so much I also purchased it in navy, shown below, and a couple of other colors. And I wrote a blog post about how to style this particular blazer here.
The photos above represent just a small fraction of the times I’ve worn these blazers. So yes, they’re expensive…and they’ve actually gone up significantly over the years…but they hold their value in your closet and the cost per wear goes down every time you wear them.
That said, there are definitely much less expensive options that will give you great bang for your buck and prove to be worthy, timeless wardrobe investments. I suggest you check out the blazers at Madewell, like the one below…
…and the blazers at J.Crew, like the one I’m wearing below. My tips for investing in a blazer are:
- fit is first. Make sure your blazer fits you nicely in the shoulders and across the back. Make sure the back vent doesn’t splay open. You do not have to be able to button it just beautifully…unless you want to.
- style should suit. Choose a style you’ll enjoy wearing. This is only as good an investment as you get wear out of it.
- color is conditional. Choose a color you love and that will mix in your wardrobe nicely. A black, navy or camel blazer is a smart investment if it will work with your wardrobe. But if you prefer a bold color, go for it. Just make sure you have the pieces to make it work over and over.
- 4-season is smart. While I love having a linen blazer in my closet for summer, I prioritized blazers that I can feasibly wear all year. The higher the investment, the more you want to be able to wear this baby!
I’ve collected some of my favorite blazers currently available below. But as we move into spring you can expect more options to surface. By the way, I size down to an 8 from my usual 10 in the Veronica Beard Miller Dickey blazers, but I wear my usual size in everything else there. I also have an 8 in the J.Crew blazer shown above.
The only timeless wardrobe investments that I didn’t mention here but might should have, include a classic black dress and a pair of classic trousers. What about you? Do you have other ride-or-die items in your closet that you’ve worn for years? I’d love to hear about those timeless wardrobe investments in the comments.
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Blessed for My Day
Some days are a battle. We’re called to do hard things. Don’t feel much like a valiant warrior? Well, rise up. Gideon didn’t feel like a courageous, skilled warrior either. But as he slowly yielded to the Lord and began to trust Him, God indeed turned him into a man of conviction and action. He can do the same with me or you if we listen to Him and obey.
Ladies, we absolutely must rise up. Our culture is looking for women who will set the example, go first, if you will. Someone is watching you. And she needs to see you be brave and courageous. She needs to see you stay with the truths of God’s Word even as they become less and less popular. She needs to hear you speak truth even when others are sharing their opinions and feelings. And she needs to see you press forward with courage when others are focusing on the past and wishing for sweeter days. And you can do this…because “the Lord is with you.”
And the angel of the Lord appeared to him and said to him, “The Lord is with you, valiant warrior.”
I’ve been purging my wardrobe and creating a capsule wardrobe with investment pieces. After retiring, I don’t need or want professional wear. Casual and tailored classics are my choices. I purchased blazers from Talbots and Madewell. Madewell has a Y-neck style blouse with the buttons for rolling up the sleeves in solids and stripes. Now I’m looking for jeans.
Thanks so much for sharing that. I do love my Mother jeans. But Madewell has good ones, as well. And I like Paige jeans, too. J.Crew usually has some good straights, but I haven’t found them yet.
Sorry James is so sick. I pray that he gets well soon. In the double faced coat did you get a 10 yours usual size in coat? I need a petite of course, but I usually wear a 10 for sweaters underneath, etc. Do you find the same too? Are the straight leg jeans high waisted or mid rise? I have really come to love straight leg jeans.
I got my usual size in the coat. And the jeans are high waisted. They list it as a 10 1/2″ Rise, but it feels higher than that to me. Thanks, James is doing incrementally better, but still needs a lot of rest.
Hope your husband gets well soon. I like all these classics. Thanks.
Thank you Rita. We’re working on it!
Dear Kay, thank you for all these suggestions. The one item I need to invest in is that trench coat…and I know it will be a good investment because belted items look good on me. Thank you most of all for your opening comments on the changes and challenges we face in our later years. As one of the missionary ladies who follows you, we have faced many challenges as well and now at our age (71 yrs old), we are facing a big decision in our lives.
I have been praying for your husband. My husband came down with the flu that went into an infection and it’s taking time for him to get his strength and energy back.
God bless!
Great pointers! In the last couple of weeks, I’ve wished that I had a classic button front blouse/shirt, but had to settle for wearing something else from my closet. I plan to remedy that soon!
Great advice Kay! And, you are spot on about transitions. While you may not have imagined your blogs influence in 2018, I am thankful … not just for “Dressed for My Day” … but “Blessed for my day”. Healing prayers for James and his Bronchitis. He has been such a vital partner with you in your blog and YouTube Channel. Thank you … and Thank you, James!
I agree with everything you said. I had never thought I should have a cashmere sweater until recently. You made a comment on your blog that cotton sweaters didn’t keep you warm in winter. A light bulb went off in my head and I thought t need to buy a cashmere sweater. Maybe it will keep me warmer. I ordered the Quince crewneck sweater. It isn’t itchy at all and I was warm and toasty in it. I’m going to stop buying cotton sweaters for winter and invest in cashmere. Thanks Kay.
Thanks for the blog today and my husband and myself had the same thing in December, but we managed to get thru the holidays. I know that James needs rest because ours lingered on because we were not able to rest much. Thanks again for carrying on!
I missed the Blessed for my Day post today! I did enjoy this post of good investment pieces.
Oh my. I did write one. But every once in a while they disappear when I publish. Thanks for letting me know. I’ll try to add one to the post tomorrow.
Ohhh Kay, does this post resonate!
First off, I am sorry to hear James has been sick. I’m more sorry to hear about your major loss leading to relocation and so many changes for you. I can relate. I have been following you since about 2019, so shortly after you started blogging. Over the years, I have left a corporate position and transitioned to being a Professor, an artist working in oils, and entered my “Mimi” era! I’ve also lost about 50 pounds. My wardrobe needs have shifted immensely, and I have studied your posts (and others) diligently to try to create a wardrobe that works for me. It has been hard for me to let go of some of my prior wardrobe needs, and I’ve wasted a lot of money pursuing a wardrobe that doesn’t truly reflect me and my true lifestyle. I think my biggest challenge has been recognizing my lifestyle has significantly changed. With that said, my priorities are so different… I will try to follow your order:
1. White button down – the crisp fabric and stark white do not suit my softer features. I have found a combination of blouses (for Zoom calls, church, dates) and elevated t-shirts work better for me. If I need an over-shirt, I prefer a cropped linen jacket or jean jacket to a longer shirt. This is also because of my body proportions, which need shorter lines than a button up provides.
2. Cashmere sweater: CHECK. I love my cashmere sweaters. Surprisingly, my Jenni Kayne fisherman’s sweater (a 60th birthday gift) doesn’t look great with my complexion, and the fisherman’s knit is too masculine for me. So I am learning to hear influencers recommendations, and reinterpret them to work with my body type, coloring, and features.
3. Full Length Straight Leg Jeans: CHECK. Actually, I truly need about 3 – 5 pair of jeans in different washes, lengths, and widths to get truly dressed for MY day. As a California girl, our formality level is different from the east coast (as is our humidity level), and denim goes so many places these days!
4. Double-faced wool coat. Not really needed in California for the most part. I would prioritize a statement jacket (like a a great leather jacket) in my soft coloring, which has been hard to find. I have a faux leather jacket that is serving me really well, and is giving me an idea for leaning into an investment into this category.
5. Trench Coat: CHECK. Must be waterproof for our rain, bonus if it has a hood to allow hands-free dashes from the car through November – April showers. I prefer a shorter version that tucks into the car easily.
6. Blazer. Oh, I’ve lusted after blazers, and have purchased more than a few, but even in my role as a professor, it feels pedantic. While this is a completely different lane, where I have found a huge wardrobe gap is in my Mimi wardrobe – soft, cozy, washable things that allow me to snuggle and crawl, and get dirty without concern. While these are not “investment” pieces, I have neglected putting money into where it is truly needed. My must-have are leisure “sets” like matching sweats from Lands End or Old Navy. They need to not be too precious/investment items, so I am not sad when they get stained, but I like them to look intentional and cute, with a matching bandana/scarf(one of my designs!) and some sneakers that work so that I can stop into an potential art client location and look artistic, credible, and put-together.
Probably a lot longer reply than intended, but this one really struck a chord with me.
Thank you for what you do, Kay. It takes a lot of vulnerability, dedication, research, and hard work, not to mention a really great support team (in James).
God bless you,
Becky
Hi Becky. So nice to hear from another California resident! I agree with your point about athleisure set. It doesn’t need to be fancy, but it’s def a staple out here. Congrats on your transformation post-retirement!
Love this post about staples. I agree with all the six items. During covid I used to”one woven item per day” to keep my outfits more polished. I know shoes are considered accessories but imho a good pair of classic loafers or ballet flats deserves a spot on the investment list. Think Audrey Hepburn.
Check out part two! 😉
Since you asked 😉 for me, a button-down white shirt is not part of my wardrobe. I’m larger in the bust area, so finding any button-down shirt where the buttons lie flat across the chest when buttoned is very difficult. And I don’t want to constantly be looking down to make sure nothing is gapping if I’m moving around. It’s a very classic-looking piece – which fits my style – but it just doesn’t work for me practically.
I have versions of most of the other pieces you’ve highlighted and look forward to part 2!
Great post! I have most of these classic investment pieces. Yes, I do have a soft ivory button down and two blazers – one in a dark brown and one in one of my signature colors; that said, none of these are often used, but I have had occasions where I am glad I had them in my closet. Cashmere sweater, wool coat, absolutely, used regularly. Jeans, I have a trouser style, which on me is a more flattering fit than a straight leg. Sorry to hear your husband isn’t well, praying for his speedy recovery.
Great items! I agree with most of those. The only one I don’t have is the wool coat. Instead I have 2 mink coats…a brown and a black. One was my mother’s and the other I bought over 30 years ago. They’re both full length. I’d love to have at least one of them made into a jacket. Anyway, either of those serve as my more dressed up outerwear piece. I can’t imagine a scenario in which I’d need a wool coat. When I’m not wearing one of my fur coats, I’m in puffer jackets, leather coat, suede coat or trench. But that’s me. Thanks for great content.
As explained before, my wardrobe underwent a major overhaul this past year due to a sift in weight. Your guidance was everything to me as I invested in this new closet. Happily, all the suggestions you made today are now in my closet and used regularly. Thank for your helping me this past year through your blog, YouTube videos and general encouragement.
That’s great to hear, Tanya. Thanks so much for sharing.