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Winter Classics Outfit Built with Investment Pieces

Building a Wardrobe
January 21, 2021

I have expensive taste. Yesterday I was shopping for bed covers at Macy’s and my eyes were immediately drawn to the most expensive bedding in the store. So it really doesn’t matter what department I’m shopping in, my eyes are just drawn to pricey items. That’s a curse. It really is. But I didn’t buy the expensive bedding, and I don’t usually buy the priciest things my eyes are drawn to in women’s clothing stores either. I’m determined to shop within my budget. But every so often I find something that I decide is worth the investment and I doggedly save for it, shop wisely for it and wait for it. That’s why today I’m sharing a winter classic outfit built with investment pieces.

Winter Classic Outfit with Black & Grey

When I looked over these photos, I almost decided not to show this outfit. What was I thinking taking photos of an outfit curated with such expensive pieces? Alas, I decided to go ahead and share them because I really don’t like wasting photos that James and I endured the freezing cold to take.

But as I began typing up this post I had another decision. Would I try to pass this outfit off as just another winter classic that you could easily construct from items in your closet or would I address the elephant on the page? I value my readers’ trust, so I decided we’d talk about the elephant.

Winter Classic Outfit with Black & Grey

This leather Veronica Beard dickey blazer is quite pricey. But, like when I purchased mine, it’s available for 25% off right now at Nordstrom (but not at Veronica Beard, where there are more sizes available – maybe they’ll price match???). I tried faux leather blazers, and I still have this one from Chico’s. But the faux leather Chico’s blazer will stay in my closet for a season, while the Veronica Beard dickey blazer is an investment that will be in my possession as long as the kitchen table my daddy built for my wedding gift. Some things are worth holding on to.

Winter Classic Outfit with Black & Grey

My AG Mari straight leg jeans were also an investment…of a different sort. While I probably won’t keep these premium denim jeans forever, I chose to pay a higher price for them because they fit and wear beautifully. And I wear them at least a couple of times a week. As a woman who pretty much lives in jeans, I like having denim that feels good and wears well. Cost per wear, I believe these jeans are a good investment.

You know, we all have our “things.” We all have certain things we’re willing to pay a little more for. I don’t use expensive skincare, drive a new car, dine at expensive restaurants (without a gift card!) or take pricey vacations. But I’m all for people who do!

Winter Classic Outfit with Black & Grey

But I love pretty clothes. And I especially appreciate well constructed clothing made with good fabrics and quality hardware. Plus fit is important to me. Not only do I want clothing that fits me well so that it looks good. I only want items in my closet that feel good on my body, too. Most of the time I’m able to achieve those goals without spending an exorbitant amount of money. But every so often I’m willing to save, watch for a good deal and invest a little more than usual in something of higher value.

My black Michael Kors handbag was not an exorbitant price, but it was a little pricier than something I would buy at, say, Target. Again, it’s a classic bag that I’ll carry for years and that I already carry very often. I purchased it on sale and got free shipping by being part of the KorsVIP program (which is totally free and open to anyone). You’ll find similar bags here and here. They’re having their semi-annual sale right now with up to 70% off.

Winter Classic Outfit with Black & Grey

Finally, my sunglasses are also a little on the pricey side. I don’t think I’ve ever paid this much for another pair of sunnies. But you know what? I’ve also had these sunglasses longer and they’ve remained scratch free for longer than any other pair of sunglasses I’ve had before, too. If I invest in something, I take good care of it.

My shoes, necklace, earrings and cashmere sweater were all very reasonable purchases. And every single item I’m wearing was purchased on sale and/or with bonus points of some sort. And, looking over the list, I can assure you I got free shipping for every piece, too.

Winter Classic Outfit with Black & Grey

I’m spilling the beans about these investment pieces because I value your trust. I’m not advocating that you make the same choices I’ve made and I’m not really showing you this outfit to compel you to purchase the items. But I do have four tips in case you do want to make similar investments now or in the future.

  1. Instead of making impulsive investments, plan for investment purchases. Create a wardrobe wishlist (I share how in this post) and chart your course. I had been planning to purchase a leather blazer for several years before I finally bought this one.
  2. Determine the characteristics you’re looking for (fit, color, quality, accents, etc.) and don’t budge on those. Resist the urge to purchase something that “will do” only to determine later on that it really doesn’t meet your expectations. (I returned a pricey faux leather jacket I’d bought in the Nordstrom Anniversary Sale, and it was hard to let it go. But now I’m glad I did. It didn’t fit nearly as well as this one.)
  3. Be patient. Watch for sales, accumulate loyalty points at your favorite stores, shop secondhand, create wish lists at the stores such as Nordstrom that have that feature and….wait.
  4. Take care of those investments and hold onto them. If you invest in classic, well-constructed pieces, I definitely advocate taking good care of them and keeping them in your closet. They’ll endure the ebb and flow of fashion fads and trends, and you can enjoy using them for years.
Winter Classic Outfit with Black & Grey

I do believe that a curated wardrobe built with a few investment pieces that you love and that fit beautifully can be a source of great joy. I also believe it can help you have a wardrobe that works for you with minimal changeover. And it helps you to be able to create classic outfits with ease and style.

Shop the Post:

You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

Coming next week…

Right now I’m working on a post that many of my readers have been asking for. I’ll be sharing how to wear socks during the winter to keep those ankle warm while also looking stylish and modern. Stay tuned!

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Blessed for My Day

Loss is a part of life. It’s huge and impactful, but it is also something we all must endure. When we lose someone or something dear, it is normal and even healthy to grieve what we have lost, that which we held dear and loved. But when have an important choice to make: will we grieve alone or will we allow the Lord to walk us through our grief.

When we allow our grief to turn to bitterness, it eventually becomes toxic and poisons every area of our lives. But when we take Jesus’ hand and walk with Him through our season of grief, we come out on the other side with compassion and insight and grace to extend to others. The story of Jacob losing his son Joseph is a story of contrast. The father grieves poorly and never really recovers from his loss. But Joseph grieves well and becomes a man marked by lovingkindness. You can read the story in Genesis 37-50.

Then Jacob tore his garments and put sackcloth on his loins and mourned for his son many days. All his sons and all his daughters rose up to comfort him, but he refused to be comforted and said, “No, I shall go down to Sheol to my son, mourning.” Thus his father wept for him. ~ Genesis 37:34-35

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xoxo, Kay
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29 thoughts on “Winter Classics Outfit Built with Investment Pieces

  1. My opinion is that if you can afford something, go for it! I’ve always liked “better” clothes, even as a teenager. (My mom will verify that; I think I drove her crazy!) I buy mostly classics and wear them for years. No, I don’t always buy more expensive things, but when I do, I enjoy them!

  2. You made me think of the leather jacket I have in the closet which my mother bought me many years ago. She only bought high-quality clothing (usually on sale), and she always looked classic and stylish. I am hoping I will get more wear out of it when we move to North Carolina. Here in New Hampshire either it is too cold or too hot to wear a leather jacket.

  3. My husband laughs at my ability to choose the most expensive item in a store, whether it’s furniture, clothing–whatever. I feel bad that you felt the need to justify or explain your expensive items. We all make choices with how to spend our money. I am willing to splurge on certain items, but like you, I am very selective. I definitely prefer to have fewer, high quality things. I am new to following you and you are quickly becoming one of my favorites!

  4. I go for clothes that look expensive but aren’t and practically never buy anything that isn’t on sale. The exception for me is handbags (only leather will do) and shoes.

  5. I find that when I save up and buy a quality item that is exactly what I want (not an impulse item) I’ll enjoy wearing it for years and years. I don’t have an extensive wardrobe, but I do enjoy every piece in it. I’m so excited about the socks post next week! I’m one of the readers that has asked that question – LOL!

  6. I appreciate you walking through the steps you take to think through a purchase. I agree with some of them and can easily see how to adjust it for my preferences. I really like the intentionality behind shopping. In years past I would just buy what I liked at the moment and sometimes that one item would not work with what I already had. I figure we all have different wish lists of for our clothes (climate, work wear, personal style…..) and for me who was not born with a natural ability to put together an outfit I sure do value your tips!!

  7. I like better quality clothes too…….but over $1,000 for a coat and $200 for the jeans. That is over the top. I think the quality of Talbots or J Jill are great and can even be a bit pricey for some things.

  8. I was raised poor so frugal is my middle name and I don’t mind buying quality used items. I do buy new investment pieces and hate the new “fast fashion” flooding the market even from what we once called quality stores. I’m not cheap but I’m careful. A lot of knock offs out there. That’s why a seasoned shopper like Kay can help so much.

  9. This is a great post and the outfit looks great on you. We all have our ‘things’ as you said. While the coat and jeans are out of my price range (and I am ok with that!) I love to see these items and then shop for similar items on ebay. I recently purchased a slightly used lambskin blazer for just $30! It is beautiful. Ebay is a great option for those who like the nice things….but want an affordable option 🙂

    1. This was an excellent post, Kay. I tend to purchase high quality clothes but fewer pieces and I find that my clothes last a very long time. Have a wonderful dBay today! Wish I had signed up for your Bible Study!!! Betty

  10. You look great in these items! Although I wouldn’t pay those prices, I can still recreate the same “outfit” with less expensive items. Your blog gives us inspiration and ideas and this blog did just that!! Please never feel you have to apologize for being you!!

  11. Kay, I always go for quality clothes but try to buy on sale. You looked great in that leather jacket and jeans…though it was a bit “pricey” for me, having been raised by my mother who grew up during the depression, and for a long time made many of her own clothes as an excellent seamstress-she would even shop for fabric bargains but always looked smart and lovely. I didn’t inherit her talent ☺️ but do splurge on quality clothes and really have too many. I loved the Blessed for My Day, my Dad passed away a bout a year ago and he lived to be 103! But I am still missing him every day. Always enjoy your fashion posts…they are just my style and you always look wonderful modeling!

  12. Great advice Kay! I am really looking forward to the post on socks! I am on the hunt for a pair of warm navy socks, so I hope you’ll let us know some of the places we can find them. I hope that you’ve had a good day.

  13. I don’t think you should apologize for expensive tastes, especially when you explain about planning for them. The jacket is not only too expensive for my budget , but I don’t like the gold buttons. I know many bloggers talk about investment pieces that you can wear for years. But it seems to me fashion changes quickly and even basic items that can be worn for years will eventually look dated with just a small change.

    1. Funny, I think basic items that you make small changes to never look dated! For an example: I am tailoring my mom’s beautiful black leather jacket with the gold buttons to a shorter version to make it more current.

  14. I also have an expensive eye. I know before the looking at prices I can’t afford what I pick out. If you have the funds, then by all means, buy what you love. It’s no one’s business how much you spend on things, I don’t judge. I might be a tad jealous. But I don’t judge people for what they spend. You have a blog and a You Tube channel. I would think you would spend more than a normal person would. Just to keep up with content. I would love to have a Veronica Beard blazer. But I don’t go out much, so it makes no sense. The only person who would see it would be my husband and my dogs. So I’ll just wear my leggings and joggers which I wear daily. When the world changes and I can get out. I maybe buying that blazer.

  15. You look gorgeous Kay!
    I think there is too much fast fashion and usually those items don’t wear or last well. It seems we really do get what we pay for and that is style that lasts and good quality.
    I want to plan ahead for some quality pieces too. My problem is instant gratification. It’s hard to wait.
    Thank you for your post.


  16. Quality over quantity, for sure! I would spend more money on perfect jeans because I love jeans and wear them a lot. A leather jacket isn’t on my want list, so I wouldn’t spend that amount on one. My daughter is obsessed with good handbags and spends way more for them than I would. So it appears that I’m thinking that if it’s something I want, I’ll spend the most that I can afford in order to get what I’ll love and wear frequently!

  17. Yes! We all have our “things” that we will spend extra on. I like nice leather purses. However, being retired and not going anywhere at this time, I don’t need any new clothes. Skincare is my current focus. No need to feel uneasy about sharing your purchases. You do you!

  18. Okay, I am going to mention this since no one else has. Could it be you feel the need to explain your expensive purchases is that you are a pastor’s wife? Pastor’s wives/ women in the ministry are often judged and scrutinized more than the average woman.
    There can be an unspoken dress code of the women in a church congregation so often women dress the same. Go to a women’s conference and you can guess who came together.
    So for many women it would be a luxury to devote so much of their budget to clothing.
    I do agree with the others it is an individual’s choice to do spend their money the way they want. I see your blog as a source of encouragement for all women to be the best they can be. It just may mean shopping at different stores / thrifting etc. for some. It isn’t about having a specific item.

  19. I feel each should do as they are impressed…if you put God (tithe and misson work) first, live within your means (no debt) and give generously to those around you…the Lord will indeed bless…Malachi 3:10. If after that, if you have the means and feel impressed by the Lord to spend $$$$ on clothes that’s up to you. I’m so thankful for my frugal upbringing…we have no debt: own our home, 3 vehicles, a camper, 13 acres, have 2 children (braces, college, etc) and no credit card debt. We also have money saved for retirement, travel, etc. and have no money stresses. I praise God for His blessings! 🙂

    1. Isn’t that the BEST feeling ever? Yep, we retired with ZERO debt. We live under our means. No need for a big house or fancy cars. We get to travel and do pretty much what we want, within reason. For me, I love and cherish my clothes/jewelry and hubby likes his stuff. 😉 I don’t like to brag about what we have though. Just feel so blessed and so grateful.

  20. The day this post was published was exactly 13 months after my grandson died. Your BFMD post is right on point. I belong to two online grief groups. One is more generic and one is faith based. I see such a difference in the members. There are so many in the generic group who are stuck in their grief, and even 20+ years later their lives have no moments of joy and no hope. The faith based group members express their ongoing sorrow, but they are still able to trust and praise God and they have more joy in their lives. They still think about their loved ones daily, but they are able to focus on the good memories.

    1. Oh wow. Thank you for sharing this Kathy. That must be so extremely difficult to lose a grandchild. Bless you for sharing your experience and encouragement with us. Indeed, we do not grieve as those without hope. ?

  21. Thanks for sharing the Chico’s jacket even though it wasn’t your fave. Wasn’t my color and body vs. sleeve length wasn’t right, but it was encouraging to see the tapered waist and belt.

  22. Kay,
    Hello again, now that I’ve found you, you’ll be sick of me and my comments! haha. I wanted to know how those jeans fit? I’m small waisted but larger in the thigh and most jeans except maybe for Talbots are thin in thigh and thicker in waist.
    I’d like to try them. I can’t wait to get out of this Pandemic so I can wear my closet full of clothes. You are a girl after my own heart, I love good quality clothes but don’t want to pay full price. I used to be a Talbot shopper then switched to Whitehouse Black Market. It seems my whole wardrobe is from them. It’s time to get into more colors.
    Thank you Kay for this blog and the Joseph Bible Study.
    Vicki Waciega