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How to Develop Your Own Sense of Style and Shop Smarter

How to Develop Your Own Sense of Style and Shop Smarter

It seems like we’ve been talking about fashion a lot these days, and we’re here for it.

From Lauryn’s latest appearance on Let’s Get Dressed, to her LTK page sharing her chic, classic must-haves and worthy investment pieces, it feels like we’re all elevating our style along with Lauryn.

And with elevating your style or revamping your wardrobe, you may find yourself craving a closet clean out. Spring is the perfect time for this which is why a few weeks ago Caitlin Jaymes came on the blog to give us all her advice on how to purge and edit your closet. It’s such a useful post so be sure to save it as a resource for when the closet cleaning bug bites.

Lucky us, because today Caitlin is back, this time teaching us how to develop our own sense of style and shop smarter. But first a quick intro if you have yet to meet Caitlin.

Caitlin is a professional organizer and entrepreneur and when Lauryn found her Bikini Organizing Bags she went to town sorting through her and her kids’ swimwear. It’s something she keeps on reordering. Caitlin is a wealth of knowledge after years of experiencing helping people organize their closets and shop. In fact, her business all started by accident. Read her first post to learn more on that.

Without further ado, let’s welcome Caitlin back to the blog.


How to Develop Your Own Sense of Style and Shop Smarter

The start of a new season usually means it’s time for a wardrobe reset. If the thought of spring shopping sends you into a downward spiral, don’t worry, I’m about to simplify it for you. By the end of this blog post you’ll be able to easily identify pieces that best suit your style and you’ll know how to shop smarter, aka no more clothes with tags sitting in your closet. Are you ready to save money, save time, and feel confident every time you get dressed? I am! So let’s get into it. 

Figuring out your sense of style can feel like the most overwhelming part of creating your dream closet. But with a few easy steps you’ll be able to tackle this challenge like a pro. 

Identify your lifestyle

First things first, you need to identify your lifestyle; be realistic with this step.

What activities are you regularly doing during your weekdays and weekends?

Are you a busy mom who realistically wears heels only once a month?

Are you a business owner who constantly needs last minute formal business meeting looks?

Are you someone who is either in full glam or lounging in sweats?

Being realistic about your lifestyle will help you prioritize items that you need in your wardrobe, recognize which pieces you’ll wear most often, and help you choose a style that’s most practical for your lifestyle. Remember – you’re allowed to have more than one style. In fact, your weekday business wardrobe could be completely different than your fun weekend attire. 

Now that you’ve mapped out your weekly routine, we can start to decide which style or styles (yes you can have more than one style) fit you best.

Look for style inspiration

For this step, we need visuals and my personal go-to is always Pinterest. Start by searching different styles so you can see what you’re gravitating towards. Different styles to search for could be preppy, feminine, minimalist, boho, edgy, sporty, sexy, classic, etc.

Start to save photos of different outfits that you would want to wear. Remember to think back to your lifestyle and save the photos that would work best for your routine. You shouldn’t be saving only sexy going-out outfits if you’re working at a corporate job during the weekdays.

how to shop smarter

A bonus tip that has helped me is to get super specific and look for inspirational photos of women who have a similar body type or features to me. This just helps you be even more realistic with yourself and to know if you would like that style on your body. 

We’re finally at the most fun part – shopping! Always make sure you start slow when shopping, especially when you’re reinventing your wardrobe and doing a big shopping haul. I find that people impulse buy the most when they hate everything in their closet and just want new pieces. 

Let’s go through a list of questions that you should ask yourself whenever you shop so you know whether a piece is a smart buy or if you should pass. These are the exact questions I ask myself.

Is the piece on your missing wardrobe list? 

If you read my last blog post on how to edit and organize your closet, you know that I always recommend keeping a list of the pieces missing from your wardrobe. This list is your “grocery list” for your closet so you stay focused and stop aimlessly shopping.

If you come across a piece that you love that isn’t on your missing wardrobe list, it doesn’t mean you shouldn’t buy it; it just may not be a priority. The importance of this list is to help you develop a complete, personalized capsule wardrobe. And to make sure that you fill in the gaps in your wardrobe. If the item is on your missing wardrobe list, then you know it’s a smart buy. 

Is this piece in a color that fits into your color scheme? 

Sticking to a color palette will just help your clothes mix and match easier. Pro tip: if you’re an online shopper, you can filter by color so you’re only focusing on colors that you know you’ll wear vs. getting distracted by the pretty pieces you may love but probably won’t wear. 

Can you find this item in your fashion inspo photos? 

If the answer is yes, but you don’t know quite how to style the item, that’s okay. Later I’ll discuss how to know if you should return items. 

How to Develop Your Own Sense of Style and Shop Smarter

Is the piece trendy, capsule, or a timeless piece? 

A lot of people are unaware of the differences between trendy, capsule, and timeless pieces. Understanding the difference between whether a piece is considered trendy, capsule, or timeless will help you shop much smarter. You’ll be able to understand what is worth your money and what is missing from your wardrobe. 


Trendy pieces are the most self-explanatory. These are pieces that you often replace after a few months or years. You want to ensure your wardrobe doesn’t consist solely of trendy items; don’t forget to mix in the basics. If you’re looking to incorporate trends into your wardrobe while still maintaining a timeless wardrobe, I would recommend sticking with trendy accessories like shoes, sunglasses, jewelry, and handbags. Trendy accessories typically take up less room in your closet. And they’re easier to mix and match with your current wardrobe. They can even make jeans and a white tee trendy. 


Capsule pieces will vary for each person and are entirely dependent on your sense of style. For example, if you have a clean minimalist style, a few pieces in your capsule wardrobe would be slim straight jeans, crew neck t-shirts, crisp button-downs, and white sneakers.

However, if you have an edgy style, a few pieces in your capsule wardrobe would be leather pants, a moto leather jacket, and black boots. A great way to find which pieces you need for your capsule wardrobe is to save fashion inspiration photos. After saving inspiration photos, you’ll start to notice that each outfit has similar pieces. These pieces should be part of your capsule wardrobe. 


Timeless pieces are the foundation of your wardrobe. They’re never really groundbreaking, but you typically wear these pieces daily. Timeless pieces aren’t affected by trends and don’t vary depending on your style.

A few timeless pieces for everyone’s wardrobe would be t-shirts and long sleeves, bodysuits, high-waisted jeans in light wash and dark wash, white sneakers, black boots, leather jacket, blazer, etc. A good rule of thumb to ensure the items you’re buying are timeless is to stay away from logos and patterns. Especially when it comes to designer handbags. Trendy handbags are fun to add to your wardrobe, but expect to change them out every year. 

Will this piece help you get dressed quicker? 

I always tell my clients (and honestly myself) to keep note of the instances where it was hard for them to get dressed. Maybe you nail your work outfits, but you’re completely lost when it comes to date night. This should tell you that you need to prioritize shopping for pieces that will help you quickly style a date night outfit. 

Do you have events coming up? 

There are always people who will shop for vacations or formal events that they don’t have just in case the event comes up. But usually, those are the pieces that are sitting in your closet with tags still on them. Usually, when the event comes up, you’re bored of that piece and want something new instead. This will be a practice of self-control – admire the pretty piece and move along because you don’t need it! 

How to Develop Your Own Sense of Style and Shop Smarter

Would this piece match well with a few of your go-to pieces? 

We all have those outfits, or at least should have those outfits, that are our go-to’s. If you come across a new piece that would pair well with any of those outfits, that’s a sign that you should get a ton of wear out of that piece and it’s a smart buy. 

Have you been eyeing this piece for longer than a week?

I recently started keeping a running list in my phone of links to pieces I want to buy. Then, to practice self-control, I wait until the end of the week to look at all of the links. Then I see if I still like the piece enough to buy it. To be honest, most of the time I’m over the piece and delete it. This is a great tip for someone who’s busy. And may only have time to dedicate a specific day to shopping. Or for impulse buyers who buy everything they see the second they see it. 

Now let’s be real, we all have those times where we may or may not have done a massive online shopping haul (welcome to my life) and you’re not sure what to keep or what to return. My biggest piece of advice is: do not remove the tags from new items until you’re completely ready to wear the item (like literally until you’re about to walk out of the door).

You want to make sure that you can style the new piece using pieces that are already in your closet. If you realize it doesn’t go with one thing in your closet, it may be a piece that isn’t practical for your wardrobe and you won’t end up wearing it.

Another quick tip:

If the piece needs to be tailored, do not put it away; put it aside so you remember to tailor it. If it doesn’t fit, you won’t wear it. 

Taking the extra time to understand your style and see which pieces you need to develop your dream wardrobe is going to make shopping such a simpler experience. Shopping aimlessly without a plan of action will result in “a closet full of clothes and nothing to wear.” Set yourself up for a successful and stylish Spring with these steps and for more fashion tips head to my Instagram or TikTok: @caitlin_jaymes or check out my fashion ebook, Style Simplified, on my website


Are you just SO inspired to head to your closet for an overhaul? Be sure to follow Caitlin on Instagram. She shares so many quick and easy style tips, that are easy to digest and totally on point with today’s trends.

What a spring staple you’re adding to your closet?

x, The Skinny Confidential team.

+ How to edit and organize your closet here.

++ The dehumidifier bags you need for all your clothes.


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