
I shop like it’s my actual job.
Wait. It is my actual job. As a personal stylist (going on 15 years now!) I’ve successfully shopped for women of all sizes, ages, budgets, and nationalities. I have built wardrobes for women in Dubai and Hong Kong and Sweden and Australia. I have scoured websites in most of the major languages and shopped in many different currencies.
I’m not saying this to brag. I’m just letting you know that I’ve shopped. A lot. And I’ve learned some strategies along the way that can make all shopping (even online shopping) more painless and less stressful.
Here, some of the secrets to shopping successfully over 40!

I hear you. Online shopping can be intimidating, but so was driving once, and most of us have mastered that. Like anything else in life, online shopping gets easier and better with practice, and it’s worth the work. I hear from so many women in smaller towns with limited shopping opportunities (like mine) who refuse to consider online shopping. That’s like saying you won’t hit the mall and will try to buy all of your clothes at the WaWa instead. Limited options can be very frustrating, especially for those of us who are hard to fit. Which is pretty much all of us. Opening yourself up to the possibilities of online shopping for the items you can’t buy locally will help you avoid a wardrobe full of compromises.

From FitFinders on websites to moneysaving plug-ins on your browser, there are so many tech tools that can help you save time and money. My current favorites are Karma (which finds coupons for you at checkout), Rakuten (money back for all of your online purchases) and ShopHoney (similar to Karma). You can also use shopping search engines like ShopStyle, Google’s camera feature to find looks similar to your favorites, and more. And most of them are absolutely free!

Have you ever had a sales associate hold a few items while you browsed and thought about them for a little bit? Abandoning the cart during an online shopping trip is kind of the same thing, but with benefits. When you walk away from an online cart, the retailer will often send you a coupon to sweeten the deal and save you even more money.

Online or off, when making a purchase of an item that’s going to be a workhorse in your wardrobe, it is worth it to spend a little more time researching the options to make sure you make the best choice. I did this when I was looking for a pair of transitional black pants. I wanted them to be able to dress them up or down, and I also wanted them to be comfortable. I ended up with 2 pairs I love (Everlane Dream Pants and Betabrand Bootcut pants), rather than just buying the first pair I saw that fit.

Another strategy I employ when shopping online is to know my numbers. Knowing a client’s current measurements (both horizontal and vertical) enables us to find the best fit online. I always include a length for tops, a rise, and an inseam length in these measurements. That way I can compare it against the numbers on the website to make sure we are getting the best possible fit.

You know all of those movie montages that show friends shopping and laughing, with multiple shopping bags in tow? Well, they hated everything they bought. They were probably carried away by the excitement and fun of shopping in a group, or talked into a regrettable purchase by a well-meaning but overly enthusiastic friend. I hate to be a spoilsport, but it’s true. Those clothes hung in their closets for years, with the tags on, before they reluctantly gave them away.
If you want to shop with friends, go pick up a new moisturizer or a great pair of earrings, and then grab a coffee or lunch. Don’t buy jeans or a bathing suit or make any other important purchase with your posse. Trust me on this. You want to take your time and really thing about these purcases. Go with your stylist (like me!) if you have one, or enlist a trusted sales associate, but for the most part, friends are not going to help you in the dressing room. They either have preconceived ideas about what you should look like and what you should spend, or they’ll encourage you to buy it all!
Take your time. Listen to your own voice, needs, and budget. And go shopping alone!

How much should you spend on shoes and bras and jeans and other potentially challenging items? The short answer: As much as it takes. Fit and comfort are critical when buying each of these items, and with shoes and denim, for example, a modern and flattering style is also critical. If you can check all of those boxes at Old Navy, go for it. But if your best-fitting pair of jeans is upwards of $100, then consider them an investment worth making. One pair of fab jeans is worth more than 20 pairs of ho-hum jeans.

I learned this lesson the hard way, as a recovering shopaholic who never had anything to wear. Put your money and your time into picking the perfect wardrobe essentials and you will never find yourself facing a closet that is filled with lots of clothes but too few options.
Which of these shopping secrets did you find the most helpful? And do you have a shopping strategy of your own that has never failed you? Let me know in the comments!
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