Over the years, friends and colleagues have asked me to accompany them on shopping trips.  My answer is always YES! (I love shopping).  Followed by, “One stipulation — you have to be willing to spend some money”.  Not huge money, but some money to invest in the pieces that will be the building blocks of your wardrobe. So, in this post we’ll deep dive into where to invest to update your wardrobe.

Let’s Set the Stage

I’m writing this post for the reader who, like me, is over 50.  You are a professional woman, and you’re thinking about investing your hard-earned money into some pieces that will elevate your style. 

I’m assuming you already have a wardrobe, so we’re talking about investing to update that wardrobe. My philosophy is that these items need to be multi-functional, appropriate for both work and casual situations (dress it up/dress it down).

You are “Investing”

A reasonable budget for these “investment pieces” is up to $400 each. Which, over multiple items, will add up.  Again, these are investments and if you think about it “per wear” the price becomes more palatable.

My style ethos does not include super expensive designer items, where one piece is $1,000+.  You certainly can spend that kind of money, but my philosophy is that you can look stylish, put together with high quality pieces and communicate your personal style in that mid-range.  So let’s go!

But First — A Few Ground Rules

Know Your Style and Body Type

Before we get into where to invest to update your wardrobe, it’s helpful to understand your current style and where you want it to evolve to.  As I wrote in this post, there are some ways to get a basic understanding of what you feel good in and what looks good on you.  Then add in the look you want to achieve and what elements can be adapted to your style. This will be your starting point.

Wardrobe Arithmetic

When thinking about putting together an outfit, I think of a core 3-part outfit – The bottom, the top and a third piece, top layer. Easy as 1,2,3!

I believe you can start with some core pieces and then add less expensive items and accessories to finish the outfits.  I’ll do a separate post on High/Low style, but for now let’s stay focused on where to invest to give you the most bang for the buck.

Quality

When you think about spending good money on items that will last, look stylish for years to come, and serve you well we’re talking about buying QUALITY. The best way to begin to get a sense for quality is to try on and feel different levels. You’ll be surprised that you actually can identify something that feels expensive vs. poorly made and cheap. This is a pretty good article, but to start, pay attention to these markers of quality:

  • Fabric — Does the fabric look and feel good. Conversely, does it feel cheap or inexpensive? Read the label — a good start is natural fibers (wool, silk, cotton, etc.). These days the fabric may have synthetics added in for stretch. Again, how does it feel?
  • Construction — You want to look at the seams and take notice of the stitching. Is it straight? The tighter the stitches are the better, generally. Are the stitches uniform? Look at the hem, lining and buttons.
  • Fit — I’m not talking about things that can be fixed with alterations, like a sleeve that’s too long. From a quality perspective, you’re looking for how the garment lays on your body. Do you see any buckling around the seams? How does it drape on your body. Is it comfortable to move in?

Okay, now let’s get into where to invest to update your wardrobe and your personal style .

Where to Invest to Update your Wardrobe, In Order of Relative Impact

Blazers/Jackets

This is going to be your top layer, #3 of the 3-part outfit and probably the most expensive item. It’s also the most visible, so you want to make sure you have good quality and fit. You will want to make sure the investment piece is classic vs. trendy.  Make sure it fits you well; that it flatters your figure.  And, it should make you feel like a million bucks.

A good blazer will look great with both slacks and jeans.  For versatility, a good starting place, would be a black one.  If you think you’ll ever have a need for a suit, buy the matching pants and/or skirt– then you’ll know you have matching bottoms/jacket in the same fabric and style.  From there, you can add coordinating, but not matching, separates. 

I purchased these matching Theory separates in grey and black about 10 years ago. They have been amazingly versatile and I still wear them today.

Photo of a woman in a grey suit, an example of where to invest to update your wardrobe.
Photo of a woman in a black suit that was an investment to update her wardrobe.
Photo of a woman in the same black blazer and jeans
Photo of a woman in a black leather jacket.

A leather jacket can be a great 3rd piece that you can dress up or down. It can act as a sophisticated layer or look awesome with jeans.  In fall/spring it can be your outerwear.

Bottoms

I’m going to focus mostly on pants/jeans.  I don’t tend to wear a lot of skirts or dresses, especially in winter, when I’d have to add tights, etc.  The exception is summer, when throwing on a dress, with bare, tan legs is so easy and looks great.  But in general, my focus is pants/jeans.

Pants

A good pair of well fitted pants (light weight wool is good for winter and summer) will be able to last you for years.  You will be able to wear it multiple ways, with multiple tops.

Brands I like: Theory, Vince, Tibi, Maeve (Anthropologie), COS, Banana Republic.

Photo of a woman in beige slacks and sweater.
Photo of a woman in plaid pants, white blouse with yellow sweater draped over her shoulders.

Jeans

Photo of a woman wearing a grey blazer, white t-shirt and jeans.

You will need 1-2 pairs of jeans in different fits/washes. I would go with a darker wash, but for interest you want some dimension in terms of fading/distressing in the thigh and butt (this can be flattering –think of it as contouring for your body). Whether you go straight, loose, cropped or flare is going to depend on your body type. I like the balance of a cropped flare and to show off my ankle boots. But again, this is going to depend on what works best on you.

I don’t think it’s necessary to spend $200+ on a pair of jeans. Brands I like that are in the $100-150 range: Kut from the Kloth, Pilcro (Anthropologie), Free People, Unpublished, Abercrombie, Madewell.

Footwear

The next place I look to invest is shoes and boots.  In my 20’s and 30’s I wore pumps and was in pain 100% of the time.  I was also not wearing the highest quality footwear, which contributed to my pain.  I’m fortunate not to have foot problems –and I want to keep it that way. 

Now, I wear low heeled, high-quality shoes/boots almost exclusively.  I look for real leather inside and out (upper and lining). And it has to be comfortable immediately. I have learned the hard way that there really isn’t a “break-in period”.

When it comes to style, you need to think about what you’re wearing the footwear with and the time of year.  I live in Chicago so it’s reliably cold for at least 7 months of the year.  As my style has evolved, I have built up a solid stable of high-quality, good looking ankle boots.  I have them in black patten, and neutral/nude. They look good with slacks, cropped pants or skirts/dresses (although I’m wearing fewer skirts/dresses lately) and, importantly, they make a statement with jeans. I would say ankle boots are a key pillar of my style.  

Photo of black patten Histanitas boots.
Photo of beige suede boots.
Photo of taupe ankle boots.
Photo of black Aquatalia ankle boots.

You will also need a good pair of flats. These can be stylish loafers, mules or flats.

If you wear pumps, add a great pair of pumps to your shopping list.

Photo of dark grey patten loafers by Paul Green.

Brands I like: Paul Green, Hispanitas, Aquatalia, Brunate, Matisse.

Sweaters/Knitwear

Sweaters and vests can also be that 3rd piece. Over the years, I have come to appreciate, and invest in, cashmere.  It is light weight, feels amazing and adds a layer that keeps me warm (Chicago, remember) without overheating (over 50, remember). The next best is merino wool.  Either way, a natural fiber is best for these for investment pieces .  There definitely is a place for synthetic sweaters to add the more trendy aspect and I’ll cover that in the High/Low article.

Brands I like: Vince, Subtle Luxury cashmere, J Crew, Banana Republic.

Photo of a woman who invested in a red cashmere vest. to update her wardrobe
Photo of a woman in a black bat-wing cashmere sweater.
Photo of a woman in black slacks, brown cashmere turtleneck and black sweater draped over her shoulders.

Bags

I’ve never been a big purse person.  I tend to have one high-quality bag that works for both seasons.

My focus is on work bags.  As I wrote in this post, here are two good ones, both in the $300 range.  This is an area where you CAN spend a lot more, but you don’t have to. 

Photo of a woman with a Cuyana tote and black leather jacket.
The Cuyana System Tote has been a great bag.

WHERE to Shop

Here is my advice for where to shop as you invest to update your wardrobe. You will want a retail outlet that has salespeople who will help you identify and put together looks. Look for someone about your age (also take note of how they are dressed) and then tell them what you’re hoping to accomplish.

My first stop is always Nordstrom. They have a range of brands and price-points and their whole model is focused on service/personal stylist. It can be intimidating, but try not to let it be. They LOVE helping people do this. If you find a good sales person, get her card. Long term, she can can be your partner in this journey to update your wardrobe and curate your style. She will also notify you of sales, and keep an eye out for other items that she thinks you might like.

Nordstrom offers free alterations, which is another big plus. This will make your purchases custom to your body.

Getting Ready For the Shopping Trip

These are my tips to set you up for success. And the biggest one is that you need to go into this shopping adventure FEELING GOOD! If you feel good, I promise, you will have a more successful trip.

This means…wear make up. Do your hair. Put on an outfit you feel good in. Wear those items that you really love. This way they can be either 1) the one to beat or 2) help you find coordinating pieces and 3) help you explain to the sales person what you like about them.

Bring the pairs of shoes you think you’ll wear with the items. If not the exact shoes, then focus on heel height that works for you. This will also help guide any alterations.

I recommend making this a solo trip. Only you know what you’re trying to achieve. You can always bring a friend back, or do a try-on later and get their opinion. But for this initial round the only opinion that matters is yours.

Finally, give yourself plenty of time. That way if you’re having good luck, you can continue with the streak. If you’re not, “cut bait” and try it another day.

Have FUN!

I really do wish I could go with you. Have fun with it. Try on things you wouldn’t normally try. And know that a few good investment pieces can truly have a huge impact on your wardrobe and your personal style. This is an investment in YOU. And YOU deserve it.

WETSU! WETSU!

XO JT

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