I’m frequently asked which pieces in your wardrobe are worthy of an investment (or splurge!) and which should remain further down the list. Honestly, how much we spend on clothing and accessories is very much a personal decision, and we all have very different thresholds. But in recent years, as I’ve been earning a paycheck and have had some disposable income for the first time in years, I have begun to invest more in a few wardrobe classics in preparation for when I retire…because that day is definitely coming! So today I’m sharing with you a few fall fashion investments you won’t regret…if you’re in a position to make those purchases without incurring debt.
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Again, this is not a post about what you should spend on what. And I’m definitely not encouraging anyone to go into debt with clothes shopping. But I’m frequently asked by readers if certain items are worthy of an investment. Like me, they’re wanting to invest a little more up front so that they can enjoy the items for years rather than purchasing all new things year after year.
The following list of worthy investments is NOT exhaustive, nor are the items listed in any particular order. But I think these are definitely some of the most worthwhile investments you can make in your wardrobe that will have lasting impact.
Leather or Suede Handbags in Classic Designs
A good handbag can make or break an outfit. I know I sound like a broken record, but it bears saying because, almost daily, I see women ruin otherwise sharp-looking outfits with worn out bags that distract from their overall appearance.
You do not have to invest thousands of dollars to purchase a beautiful bag that you will carry for years. But I have learned about myself that when I spend a little more – say $200 or more (for me) – I’m much more prone to take care of the bag and keep it in good condition year after year. I’ve had the Tory Burch McGraw hobo bag for about five years now and it looks like new.
I’m going to let you check out my recent blog post, Stylish Handbags for Fall 2025 if you’re interested in purchasing a new bag for fall. But here are a few things to look for when you choose to invest a little more than usual in a quality bag:
- Generally you want 100% leather or suede. Look for a supple fabric that feels good to the touch.
- Even stitching that features small, secure stitches and no gaping threads, knots or tangles.
- Good quality hardware, including zippers and fasteners that work well without struggle.
- Lining inside the bag that fits the bag nicely and is constructed just as beautifully as the exterior. On the other hand, I often prefer bags with no lining at all, so that’s another option. (My Tory Burch McGraw hobo is unlined and I think that makes it more exquisite.)
- Features that you personally prefer, such as zip pockets, additional open pockets, closure types, flat bottom, feet on the bottom, strap size and additional interchangeable strap options. Don’t sacrifice on these personal preferences just because someone else has and loves a certain bag. You want to invest in good quality, but you’ll only use the bag if you love wearing it.
Good Quality Cashmere in Colors You Love to Wear
Granted, not everyone wears cashmere. But if you do enjoy wearing cashmere or even wool sweaters, these are a good investment. I’ve had many of my cashmere sweaters in my wardrobe for five and six years. Choose to invest more in sweaters in classic silhouettes and lengths, such as a basic crewneck, v-neck or turtleneck, but again, I recommend buying only sweaters you’ll truly enjoy wearing.
When it comes to colors, remember they never really go out of style. So if you love them, you will find a plethora of dark brown, peridot green, sky blue and deep cherry red sweaters available this year, and you could invest in one of those colors with confidence. However, you may prefer to invest in a neutral that you can wear with confidence year after year.
Premium Denim that Fits Beautifully in a Classic Silhouette
There truly is a difference between the jeans at Gap and the premium brands such as Frame, Mother, Paige and Rag & Bone. That’s not to say you can’t get great jeans at Gap or other similar retailers. You absolutely can. I have and wear non-premium denim. But the jeans I love wearing the most are from those premium denim brands…and Madewell and J.Crew.
My Frame jeans (and similar from same brand) above are a good example of a great premium denim jean. They denim is 90% cotton, 6% elasterell-p, 4% elastane denim has a lot of stretch, but they do not stretch out as I wear them. That’s definitely one of the biggest differences. But the other details are just as noteworthy. The dye doesn’t bleed and the wash is a beautiful black. The fading is artful and the whiskering is subtle. The hem looks authentic and the stitching is small, even and a high stitch count per inch. The pocket placement is nice and the front pockets lay flat, as does the zipper placket. Let’s face it, these are details that other brands sometimes fudge on.
But most importantly, these jeans fit me nicely (I did size down to a 29), and I enjoy wearing them. So, as with all of these worthy investments, they’re only really worth the price you pay if you love them and wear them. For a wide selection of premium jeans as well as other more moderately priced options I highly recommend, check out my blog post, These Popular Jeans Will Make You Look Younger.
Comfortable, High Quality, Fashionable Footwear
Dear friend, it is time to stop buying any shoes that hurt your feet. And at this point we should only invest in shoes that we can wear frequently and for at least half a day without damaging our feet. At the same time most of want to still wear fashionable footwear. Fortunately there are plenty of options available today in comfortable, high quality, fashionable footwear to help you step out in confidence. There’s just one problem…
Generally, you have to pay for it. I’m gifted a lot of footwear, so I have a closet full of investment worthy shoes. But if I didn’t receive those gifted shoes, I would absolutely be content with a smaller collection of high quality footwear rather than purchasing dozens of shoes each year that either fall apart or make my feet fall apart. Check out my blog post, 5 Shoes You Need in Your Fall Wardrobe for some shopping options. And you can see my favorite Ally Shoes – the most comfortable dress shoes and boots I’ve come across anywhere – in my post How to Choose the Right Shoes for Your Fall Outfits
Good Quality Belts in Leather or Suede
Coming soon I have a video about accessorizing your outfits. In that video you’ll hear me say that one of the main keys to accessorizing your outfits beautifully is simply having the right bags, shoes and belts in your wardrobe. Accessories aren’t just the icing on the cake; they’re the icing between the layers of the cake. They hold your outfit together, helping you to look polished and pulled together.
Like a handbag, a belt can make or break your outfit. Look for belts with small, even stitches that are well sewn. Look for good hardware and supple leather or suede. Invest in a belt that fits you nicely (ideally you want to use one of the middle holes in the belt if it has the traditional 5-7) and that is in a color you wear frequently in your handbags and/or shoes. Follow the size guides when purchasing a belt: sometimes they follow industry standards and you wear the same size as you do in garments, but other times they don’t.
Suede or Leather Garments or Accessories in Classic Styles
Finally, for this list at least, let’s talk about investing in suede or leather garments and accessories. Leather is definitely the classic fabrication of accessories, and its variant suede is just as timeless. It can be so exciting to invest in a substantial garment or accessory in a beautiful leather or suede.
My biggest recommendation here is to invest carefully in a piece that has classic lines and details. For instance, even though fringe is a big trend right now and you will undoubtedly see suede jackets and other garments featuring this boho detail, I personally would not invest in a suede garment or bag with fringe. That fringe is not classic, and it’s going to date the item.
On the other hand, you can invest with confidence in a suede or leather blazer, trench, car coat, mac or skirt. Those items will look timeless and you’ll enjoy wearing them year after year. Below I’ve gathered other options that I could heartily recommend as investments you won’t regret. While faux suede and leather probably will not hold up as well over time, they are beautiful alternatives. So I’ve included some of those, too.
I hope my ideas on investments you won’t regret have been helpful. This post was not meant to be exhaustive. There are certainly other investments you could make in your wardrobe that would be just as sustainable. Did you make a wardrobe investment years ago that you’re enjoying today? I’d love to hear about it in the comments.
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Blessed for My Day
I’m so grateful for my salvation through Jesus Christ. I don’t deserve to live eternally in heaven, much less to have a relationship with my Creator. I’m a sinner, condemned and unclean. But God so loved me that He sent His Son to earth to live a blameless life and die on the cross in my place, paying a debt I could not pay and He did not owe. Because of His sacrifice I can now have a thriving, growing relationship with the Father, and I have the Holy Spirit within me, helping me to live a life that is more pleasing to Him.
If you do not have that kind of relationship with God, but would like to, I invite you to check out this page on my website. There I will walk you through a few verses in the Bible that will help you see yourself more clearly and show you how you, too, can have eternity in heaven and a relationship with God right now. You’ll absolutely love getting to know Him more and more.
Blessed be the God and Father of our Lord Jesus Christ! According to his great mercy, he has caused us to be born again to a living hope through the resurrection of Jesus Christ from the dead. ~ 1 Peter 1:3
Hi Kay
Really enjoyed the post today, I think I am more a ‘classic’ person when it comes to style.
Some 18 years ago, whilst shopping with my sister for a mother of the bride outfit for her I tried on a brown suede blazer type jacket with leather collar and cuffs. It is one of my favourite items in my wardrobe, I still wear it and get complimented on it!
I agree, some well-chosen, quality classic pieces really can have longevity in one’s wardrobe! I don’t have the budget for truly investment pieces (like premium denim), but I try to buy real leather shoes and handbags and I take good care of them to get years of use. I also get decent denim and cashmere (usually, Talbots).
I shop at Nordstrom, Loft and Evereve and I have items in my closet for years and usually only get rid of them because I’m tired of them or they aren’t in style so much anymore, like skinny jeans. I really think if you look for good quality items even in these stores it’s how you wash and care for them that really helps. I rarely ever dry my clothes. It’s a pain to lay out items, but worth it. I don’t dry my jeans either. I just can’t justify buying from some of the stores you feature, but love seeing what you post as they are cute. I guess I’d be afraid to ruin or stain a blouse that is $200 or more. Will be hard to see you retire someday. So fun to follow your blog. Maybe you could still share your outfits? lol
I most regret buying what I think of as bargains that really aren’t because I don’t wear them so much. I’ve had a Scottish tweed jacket for over 20 wears and an Irish tweed for 15. I gulped and paid full price, and it turns out they are real bargains. I’m planning to wear them a lot this winter.
Have a great time.
Great post. Thank you.
My investment pieces that come to mind that have been workhorses for me foe many years are my black leather riding boots, black leather blazer, Harris tweed blazer, and I do have a weakness for quality designer belts and bags.
Great suggestions!