How to Shop Like a Pro: The Exact System I Use to Shop for Clothes

I just received the following email and thought it would be a great question to answer here:

“have you ever done an article on how to shop? i feel like i absolutely LOVE fashion and know what i would like to dress like, but when i go shopping i get completely overwhelmed and have no idea where to start- especially in big stores. do you have any tips about HOW to shop? i dont know if thats a dumb question or not lol but like i said- its overwhelming. i wish i could translate all my ideas about what i love into shopping!”

I don’t think it’s a dumb question at all, and I know just as well as anyone how tough it can be to translate what you WANT to wear into what you actually end up buying. It takes work to create a wardrobe, and achieving the look that’s “you” often takes planning and hard work!

Since I’m a list-maker to the core, I have a whole system for this exact problem. Here are my tips for shopping with a certain look in mind:

Take notes on the looks you like.

Keep a “fashion inspiration” notebook (or Pinterest board, or Instagram collection), where you save photos of looks you like, celebrities wearing outfits that inspire you, or whatever it is that gets your inspiration going! If you have a favorite fashion muse, save photos of what she’s wearing so they’re easy to reference.

Personally, I use Instagram for this. I have a “Style” collection that I constantly update with everything I come across that inspires me. Whether it’s an influencer wearing a certain outfit, a throwback Vogue shot, a picture of a celebrity or just a pair of shoes I want to get, I save everything to that collection so it’s all in one place.

I also get more organized than this — I have separate collections broken down by season. The above screenshot is my “SS19” season collection, with only looks that will inspire my spring/summer closet. When we get closer to fall, I’ll start a new collection for the cold weather.

Also Read: Shop Smarter, Not Harder: Save Money in College

Deconstruct the looks piece by piece.

This is really important. Once you have your inspiration in one place, you have to deconstruct it to get a sense of what you’re actually looking for. Smart shopping takes some planning ahead!

Start by asking yourself a series of questions.

First, find out what about the look appeals to you. Do you love the clothes or simply how they look on that person? (If you aren’t sure, picture the outfit on someone else – would you still love it just as much on a different person?)

Then think about the general aesthetic vibe. Is it boho-chic, goth, edgy, preppy, or something else? What does it remind you of? Get a sense of what appeals to you and write it down.

Now deconstruct the outfit. What are the individual pieces involved? Make a mental list of them all. Do you own any of the pieces already? If so, which extra pieces would you need to buy to emulate that look? Write down a list of those.

Eliminate pieces on the list that won’t work for you.

Now that you have a big list of pieces you’d like to own, it’s time to eliminate anything that won’t work with your style or budget.

Start by analyzing how trendy each piece is. Is it the kind of thing that will be over in a few months, or is it a classic that will never go out of style?

If your piece is trendy, how often do you think you’ll wear it? If it’s the kind of thing you’ll only wear once or twice, eliminate it altogether. It’s not worth your money.

Keep going with this to evaluate each piece against your personal style. Is the outfit the right color for you, or would you need to buy a piece in a different shade? If it’s a specific piece that only comes in a color that won’t work on you, eliminate.

Figure out what to spend and what to save on.

This will be different for everyone depending on your budget and how often you’ll wear something.

My personal rule is if I’ll probably only wear it a few times and it’s not for a super-special occasion, I’ll buy it on the inexpensive side. (Although I am generally trying not to buy things I know I won’t wear that much — quality over quantity and all that!)

If it’s the kind of thing I know I will be wearing a lot, like a pair of dark wash jeans or a well cut blazer, I’ll splurge on it. (I always calculate cost per wear here!) Quality is important when it comes to the things you wear on a daily basis. Also, I have a personal rule that I never, ever buy cheap ($20 or less) shoes — I’ve learned that lesson the hard way.

If you need more guidance on this, CF writer Arissa shared the exact system she uses to decide where to save and splurge.

Once you’ve figured this out, take your list and divide it into two sub lists – Splurge On and Save On.

Have a game plan before you set foot in a store.

We all know that bad things can happen when you go shopping without a list of what you’re looking for. Impulse purchases are so easy to make, and they often leave you with a closet full of clothes you don’t even like that much!

Moral of the story? Always be prepared before you go shopping. Here’s how:

Start by shopping online if possible. Of course, I don’t mean you should be BUYING everything online. Instead, take your lists of items that you made and look for similar pieces online. This way, you can compare prices easily and find the best deal on what you want.

Decide what you want to buy where, and write it down! If you’re not sure exactly where to get something, that’s okay.. but if possible, make a list of stores you think might have that piece.

Go to a store and try things on!

As much as I love online shopping, I usually like to buy things in-store, especially if they’re expensive items. This way I can try things on and get a feel for how things look in person. Sometimes online photos can be really inaccurate, so shopping in-store allows you to touch the fabric, look at its movement, and see how things fit on your body.

By the time you set foot in a store, you should already have a detailed list of what you plan to buy there. No wandering randomly into Forever 21 and picking up whatever catches your eye!! Have a plan and you’ll save yourself a headache, end up with quality pieces, AND spend less money.

Next, find the items on your list and get into that dressing room! Try things on and if you don’t like how they fit (and you don’t think they can be altered), don’t be afraid to look elsewhere. Shopping can be hard work and if you want a fabulous wardrobe, refuse to settle for “just okay.”

Repeat the process.

If you’re really into fashion, you’re probably inspired by new things, and therefore wanting to update your wardrobe pretty often. That’s okay, so long as it’s in your budget to do it. If not, you’ll have to plan accordingly. Either way, you can keep applying this system on a regular basis.

Personally, I’m always updating my fashion inspiration collection, keeping track of new trends I want to try, and scouting online for where I can find the best deals. I don’t buy everything I want (obviously), but I try to update my wardrobe often enough that I don’t get bored. Of course, I also have a budget that I stick to. While keeping your wardrobe fresh is fun, having enough money to buy books and food is a lot more important.

Whenever you see a look you’d like to incorporate into your wardrobe, repeat this shopping process and you’ll end up with a closet full of clothes you love. The more you do it, the more it becomes like second nature. After you do this a few times, you’ll instinctively know what to buy and where.

Your Thoughts?

After reading this guide, what do you think? Do you have a system like mine for shopping, or do you just browse the racks and buy whatever looks cute at the moment? Do you have any shopping tips of your own? Leave them in the comments!

Editor’s note: This post was originally published in 2009; it was completely updated and revamped in 2019 with new photos and information.