How to Shop For Investment Wardrobe Pieces

We talk a lot about the new fashion here, but today, I want to switch things up and talk about how to shop for investment wardrobe pieces that will save you both time and money. I don’t add many new pieces to my wardrobe each season, and I’m very particular about the ones I do. I also own and actively wear pieces I’ve had for 25+ years.

A white T-shirt is an investment piece for some women, but I never spend much on mine because I like to replace them often. My Paul Green sneakers are an investment because they’re super comfy, and I’ve worn them for many years. My white button-down shirts also get dingy, so I never spend a lot on them. My point is that a timeless item in your wardrobe will be unique to your style.


Your investment items will vary according to your budget, lifestyle, and location and do not have to be a luxury brand. They need to be worth investing in for your specific style needs and provide versatility in your wardrobe.

Understanding how to shop for timeless pieces is key for women who want to curate a wardrobe that transcends seasons and trends. This guide is your compass to navigating the world of fashion choices, ensuring every piece you purchase is not just a garment but a long-term asset to your personal style.


1-What Is An Investment Piece?

Investment dressing has become even more important in today’s fashion landscape, which is often dominated by disposable styles and fast fashion. These wardrobe staples are not trend-driven and are often your wardrobe VIPs. They needn’t be designer pieces with an astronomical price tag, but they are of higher quality, so they will have longevity in your wardrobe. They’re often classics that never go out of style, like the cashmere sweater you reach for year after year and that perfect blazer that pulls any look together. It can even be the perfect pair of denim jeans that you always feel amazing wearing. The key is that they have a timelessness in your wardrobe. If your personal style leans toward boho, your investment pieces will match that aesthetic.  

2-Quality Over Quantity

When it comes to building an investment wardrobe, the adage “less is more” couldn’t be truer. As with a capsule wardrobe, you want to focus on quality, not quantity. Look for garments and accessories made from high-grade materials that will stand the test of time. The seams should be straight and stitched with small stitches. Patterns should line up, and there should be no hanging threads. Boots should be water-resistant if you live in a rainy climate, and the craftsmanship should be obvious. Buttons should be securely fastened and zippers smooth.


3-Essential Investment Pieces Every Woman Should Own 

Every stylish woman has her go-to investment pieces. A great cashmere sweater, my classic Cartier watch, a quality handbag, my Louis Vuitton wallet, and a pair of well-fitting jeans are non-negotiables for me. Your style and lifestyle may need a wool coat, a classic pump, or a floral blouse. The point is that these are the pieces you reach for year after year, so they are worth spending a bit more for. I find quality accessories are always a wise investment that adds a touch of elegance to your outfit.


4- Where to Shop for Investment Pieces 

Online shopping can be a treasure trove if you know where to look (and make sure they have a good return policy!). Don’t overlook the value of resale when building your investment wardrobe. When considering resale, make sure to choose platforms or stores that have a reputation for curating quality items and providing fair authentication and pricing. I’ve found some wonderful treasures at Fashionphile and The RealReal. Thrift and consignment stores can also be goldmines for high-quality, lightly used pieces at a fraction of their original cost.


5- The Importance of Personal Style

While investment pieces are meant to be timeless and versatile, it’s important to consider your own personal style when building your wardrobe. Whether you have a love for minimalism, bohemian vibes, or sophisticated elegance, your investment pieces should embody your personal style and make you feel confident and comfortable. 

6-Budgeting for Quality

Plan your purchases, set a budget, and be patient. Wait for sales or save up for that special item. Remember, the cost-per-wear of a high-quality piece often turns out lower than a cheap, quickly discarded item. Investing in one piece at a time allows you time to get just what you need rather than settling for less.


7- Sustainable Fashion and Ethical Considerations 

In today’s world, it’s essential to consider the environmental and ethical implications of our fashion choices. When investing in pieces for your wardrobe, prioritize brands and retailers that adhere to sustainable practices, use ethically sourced materials, and promote fair wages and working conditions. Opting for quality over quantity and choosing pieces that have a lower impact on the planet helps create a more sustainable and conscious fashion industry. More and more, I am looking to invest in pieces from brands that are Certified B Corporations which means they’re leaders in the global movement for an inclusive, equitable, and regenerative economy.

Jennifer Connolly of A Well Styled Life wearing white linen suit

8-Caring for Your Investment Wardrobe 

Taking care of your investment pieces ensures they last. Follow care labels meticulously, invest in good quality hangers, and store items properly. I swear by these clear plastic bags to protect my blazers and cashmere sweaters from moths. Consider professional cleaning for particularly delicate or high-end pieces. This attention to maintenance not only preserves your garments but also your investment in them.


Investing in high-quality items may initially seem more expensive, but in the long run, it’s more cost-effective because these pieces are durable and can be worn repeatedly which decreases their cost per wear. 

I like to think that building an investment wardrobe is like curating an art collection. It takes time, a discerning eye, and an appreciation for quality. Start with one piece and build from there. 

What investment pieces do you have in your wardrobe?



  1. Jennifer, what brand is the investment skirt you featured? I love it. It reminds me of a CP Shades Lily skirt, which I’ve never tried on. I don’t live close to a store that carries it. And would hate to pay reurn shipping if it doesn’t fit.The Lily skirt comes in different fabrics and colors, but I wonder if the length would be too long – I’m 5″ 1″. If it was too long it would be expensive to get hemmed. I like the fabric of your skirt and color. Also, if the waist isn’t elastic it wouldn’t flex with my gain 10lb. lose 10 lb. yo-yo waistline. Please let me know the skirt brand and size you picked.

    1. It is a CP Shades skirt in size S. I can wear it with plenty of weight fluctuation. I love it! I think it will be too long on you. Here’s a solution… have them hem it from the top! They just cut the elastic off, remove inches of fabric and make a new waistband for the elastic. I do it all the time.

  2. This is a great post! I love your outfit with the vest and hat, and the Eileen Fischer outfit looks so great; it reeks quality! I want my whole wardrobe to be like that!
    I struggle all of the time with the pull and tug of quality over quantity. I don’t necessarily buy cheap pieces, but I buy too many clothes that I end up not liking, and then I give them away! I think my issue is my fluctuating weight. I need things to wear at the weight I currently am, I own many things that don’t fit, I’m trying to lose weight..and this vicious cycle continues. I hate to invest in overly expensive pieces at my current weight, but I still want quality items, and still want to look stylish always. What to do? I wonder if any of your readers struggle with this. What would be your advice?
    I love the quality look of wool whether it’s a coat or a cashmere sweater.
    Can you suggest a quality alternative to wool as an investment piece and where would you shop for that? Thanks Jennifer.

    1. I would suggest you do invest in one or two pieces that fit you perfectly now. It’s no fun to wear clothes that don’t fit and you deserve to feel fabulous in your clothes. A great pant in a neutral culd be worn repeatedly without being memorable. If you do lose weight, the quality pieces you’ve invested in are worth having altered to your new size. Cheap clothes just don’t feel as good as quality pieces and you deserve to treat yourself nicely.

  3. Jennifer, I have learned a lot from you about my personal style, which has helped me figure out what kind of investment pieces I need. The key thing for me is patience in looking for those investment pieces, and not settling for “good enough.” It can be frustrating, but I have enough basics now to form a foundation for my wardrobe while I am on the hunt for those special pieces. And also, thanks to you I keep a list of what I need. That helps keep me on track!

  4. GREAT article, Jennifer. I read every word and must say that I agree, and your ideas are thought provoking. They help fill in some gaps in my own thinking as to where I want to go with my wardrobe. The wardrobe is like a curated art collection—-I love that! SO TRUE! I invest in leather bags and wallets, as well as classic loafers and mules, plus athletic and street sneakers. A great pair of black dress pants. I have some fine jewelry, as well. If I’m not going to wear an item multiple times over multiple seasons, I tend to spend less money on it, and as you mention, cost per wear is a huge factor.

  5. I am in search of a classic navy blue blazer. I have had several in years past that I loved but they’re long gone:( Any suggestions of places where you have purchased one that you love?

    1. I Love Talbots for classic like that. Ann Taylor also has some as does J.Crew.

    2. I’ve been looking for the right navy blazer too. I can’t find a navy that’s bright enough for my spring coloring. I tried J Crew’s Willa blazer, but I might as well have been wearing black.

    3. Sharon K. says:

      Pendleton Woolen Mills has a beautiful wool and lambs wool classic blazer, available only in navy. Might work!

      1. Thanks Sharon

  6. Christine Arquilla says:

    I have 2 clothing budgets, one for investment pieces and another for more trendy items. My first ever investment item was an Evan Picone long black lambswool dress coat that I bought in 1983 for $300. I retired it about 15 years later, amotizing the cost to 5.48 cents a day. I just replaced the blue wool chesterfield coat that replaced it with a forest green mid-calf length Karl Lagerfeld wool coat that has a gorgeous removeable faux-fur collar (which was a sale find for $170). Other investment pieces are a Ming Wang black dress, 3 pair of trousers, and skirt that I use for work and travel that I bought back in 2012. They are still going strong today. I wear various shells, tunics, and blouses with them and treat myself to one of the brand’s gorgeous jackets a year. I’m actually spending less on clothes since I got them than when I was buying “cheaper” clothes and am no longer a slave to every trend that comes along. By the way, you look fabulous in your vest and hat in the last photograph. Cheers!

    1. That coat sounds amazing! Thank you

  7. I started replacing my entire wardrobe last February. Your blog has helped me so much in defining my style, buying on sale, realizing I am a casual fashion person. My investment pieces have been jeans from Chicos because they fit and are extremely comfortable and discovering Skechers shoes. I have a lot of pain in my feet and these shoes have given me so much relief. I had my hair cut in a similar bob to yours and I love it. I live in southern Colorado in a small rural mountain town so the dress is very casual. My knee length down coat with faux fur around the hood was an investment several years ago from LL Bean. It is warm and stylish and I love it! Also my UGG boots were an investment for me but they have lasted for years and are exactly like the ones they are still selling. Thank you for all the ideas you give me. I read your blog everyday and love it.

    1. Classics endure and are such a smart way to build the backbone of our wardrobes! Thank you for being a great part of our community, Sydney.

  8. I think my longest lasting investment piece is my camel wool winter coat. It never looks out of style. I like investment piece jewelry. My mother’s pearls and my late husbands gifts.

    1. Those are treasures!

  9. Investment pieces are individual. Some pay big prices for jeans. I wear jeans all the time and find mid range that fit perfectly and last. I don’t see the benefit of highly priced jeans. I’ll pay a bit more for a classic button down but not outrageously. I’m with you tees. They yellow under the arms so I like to refresh them yearly. I like a leather purse but you can find them under $300, not in the thousands. I will not buy designer labels. It’s pretentious, in my opinion and certainly not quiet luxury. I just can not justify some of the prices I see today. It’s not value, in my opinion.

    I need a new fuzz remover. Mine is old and not doing a great job anymore. Do you highly recommend the one above?

    1. I love the gleener and sweater shaver.

  10. Sharon K. says:

    I have three of my mother’s 1960s beaded evening bags that I use for special occasions. They never wear out or look dated.

  11. Quality pieces that are essential to me: a good winter puffer coat with down, warm winter boots, hats and gloves/mittens, leather shoes, and a leather handbag. None of these are designer. None cost thousands of dollars. They did take extra time and effort to find. Simplicity carries these items from year to year. I have never found a decent puffer coat on consignment in my size, so I start the search for sales in advance of needing a replacement (when my coat sheds too many feathers).

    I look for cotton and linen in my summer clothes. Finding these materials is getting harder, as retailers source ever cheaper suppliers. It’s disappointing and not worth my money to settle for poor quality. I don’t spend a fortune on these items, but also can’t abide throwaways.

  12. Hi Jennifer, I love a European brand that isn’t as well known in North America – Marc Cain. Quality fabrics and construction, timeless style – I have owned Marc Cain pieces for years. Their classic t-shirts, for example, don’t stretch, lose their shape, pill, or fade. I have some that are 15 years old that still look new. The cost per wear is miniscule.

    1. I’ve never heard of Marc Cain. I’ll check them out.

  13. For so many years, while raising my family and working, shopping for myself was very random. I had a closet full of clothes but struggled to put together an outfit that I could say was one that I loved.
    Honestly, your blog has taught me to be more mindful of my shopping. For me, a basic wardrobe works the best and I can accessorize to add my personal style. Quality shoes, quality handbags or well fitting jeans are so worth the cost. They will get repeated use, year after year.
    Today, my favorite accessory is a swipe of lip color and a hair cut/style that allow shine and movement!
    You’re an inspiration Jennifer! Thank you!

    1. You make a great point Jan. I’m lost without a swipe of lipstick!

  14. Jennifer, I ordered the long Amazon sweater you featured the other day. It arrived yesterday and I was pleasantly surprised at how nice it is. Yes, it is long – great for me because I am tall. I got the red – it is a nice cherry red and will be perfect for Christmas, but also many other times of the year. It is simple, but a nice weight and the way the collar comes up around the neck makes it cozy and warm. I don’t remember the cost, but well worth it.

    1. I’m glad you like it too. The quality is fabulous!

  15. Hi,
    This is such good advice. What type of Cartier watch do you have-leather strap tank or stainless steel bracelet? I bought a pre-owned one and am thinking about selling it, but now having second thoughts as it is a classic piece. The stainless steel is a bit dull not sure how to get it shinier or if that’s the way it’s meant to be.

    1. I have a stainless tank my husband bought me over 40 years ago. Two years ago I had a jeweler send in so Cartier could refurbish it and it came back looking brand new! In fact, I thought they’d swapped it for a new one. My metal is brushed but it’s now a shinier brushed if that makes sense.

  16. Melinda Beckett says:

    I have been following you for 2 years and love your posts, but I think investment shopping is your real gift to offer us. You show us how to shop, what is a wardrobe stable and when to let go when we are in a rut! Thanks for your help, insights and you are always telling us to have confidence in our style. Brava, girl!

    1. I’m so glad to be helpful.

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