We’ve all been there:

Shopping online, excited by the purchase of an amazing shirt or sweater, then disappointed when the item arrives and fits horribly.

How does this even happen? You know you're a size medium... and you ordered a medium!

Well, unfortunately, there is no universal size small or medium. A medium from one brand will fit you a little differently than a medium from another brand.

Fit aside, there are a handful of concerns when shopping online:

  • Will you like the materials it’s made of?
  • What happens if you flat out don’t like an item when you receive it and need to return it?
  • Etc.

So... how do you get the huge benefits of shopping online, without the headache?

While it can sometimes be intimidating, with the right knowledge and a little bit of preparation, it's easy to be an online shopping expert.

In this post, I’m going to give you 7 simple steps to buying clothes (that you’ll love) online.

7 Foolproof Steps to Buying Clothes Online

Before we jump into our 7 steps to buying clothes online, I want to quickly touch on “why” of online shopping.

Why, with the difficulties that come with online shopping, would you even do it in the first place?

Well... there are three huge benefits to shopping online:

Reason #1: Lower Prices – Not only are clothes generally cheaper online, there are a handful of clothing “flash sale” sites (like Ideel) that offer clothes at significantly discounted prices, for a limited period of time.

Reason #2: Better Display Capabilities – Clothing stores have limited space to display garments. While you'll see a handful of items prominently on display, the majority of the store’s clothing is hidden in the racks. Shopping online puts each and every item prominently on display so there is no need to search.

Reason #3: Convenience – You can get your entire wardrobe delivered right to your front door, without leaving the comfort of your home.

Preparing to Shop Online (3 steps)

Before you start shopping online like an expert, there are a few preparatory steps you need to take:

Step 1: Get your exact measurements from a professional

You might be wondering:

Without trying a garment on, how can I be sure it will fit me?

The secret to buying clothes online...

...is to compare your exact measurements with a garment’s sizing chart.

What’s a sizing chart?

Accompanying every item you see for sale online will be a chart that translates typical sizes (small (S), medium (m), large (L), extra-large (XL)) into exact measurements.

Here’s an example of a Blake and Woods V-neck sweater:
From the chart above, you can see that a small sweater measures:

Neck: 13.5 in

Chest: 34 in.

Sleeve: 32 in.


Your first steps to becoming an online shopping expert is to get exact measurements of your body, in the places important to buying clothing (like the neck, chest and sleeve). Using these you’ll be able to scan any sizing chart and quickly determine what exact size you are in a specific garment.

To make sure you get your exact measurements, we’re going to enlist the help of a tailor.

I’m sure you’re asking:

Why can’t you just do the measurements yourself at home? Honestly, you could... but you need to look at this like an investment.

Over time, you’re going to be spending hundreds, if not thousands, of dollars on clothes online.

A tailor will maybe take an hour and will cost you $20-$30, but will also ensure that all of your measurements are exactly right.

If you want to roll the dice and measure yourself...

...use this guide from the Art of Manliness.

Pro tip: I highly suggest you create a Word, notepad or Google doc on your computer to keep a record of what you find in steps #1-#3. This document will also give you quick access to all your important online shopping details.

Step 2: Know what materials you do and don’t like

Have you ever put something on and immediately wanted to take it off because it was so uncomfortable?

Different garments are made of different materials: cotton, wool, silk, down, denim, etc.

Not only are different materials more or less comfortable to different people, your living conditions and wardrobe may benefit from a particular material.

For example:

If you live in a colder climate, wool and down are going to provide you with a lot more warmth than cotton and denim.

The easiest way to determine which materials you like best, and are the best fit for your lifestyle, is to look at the materials of clothing you already own.

So... go to your closet and pick out a handful of your favorite items and look at the tags.

What materials are they most frequently made of? Add these materials to the document you created in the previous step.

Step 3: Know what styles/cuts you like

Boot, athletic, regular, relaxed, slim.

Just like any other industry, the fashion industry has its fair share of terms and lingo. Terms like boot, athletic, regular, relaxed and slim are used to describe a garment that fits in a specific way.

For example:

A slim fit shirt will be narrower and tighter fitting in the arms, waist and chest versus a regular fitting shirt.

To help you determine the cuts/styles that are best for you, we’re going to again examine items from your existing wardrobe. While the terms will vary depending on what item you’re looking at (shirts, pants, etc.), here are some terms to look for:

For shirts:

  • Slim fit
  • Regular/Traditional fit
  • Athletic fit

For pants:

  • Slim
  • Regular
  • Relaxed
  • Loose

How to get the right fit/item once you find something you like (4 Steps)

So... you’ve found an item you like online and want to know if it's right for you?

It’s time to use the information you found in steps #1-#3 above to ensure that it not only fits well, but is an item you end up loving.

Step 4: Reference the item’s sizing chart and determine your size

Remember the sizing chart we talked about in step #1? Here it is again:


Take the measurements you got from the tailor and find the size you’re closest to (but still under). For example, if the tailor gave you the following measurements:

Neck: 14 in.

Chest: 36 in.

Sleeve: 33 in.

You would be a size medium (M) in the Blake & Woods V-neck Sweater above.

Step 5: Read the product descriptions

Once you’ve determined the right size for a specific item, it’s time to dig a little deeper and check out the product description. This description will give you invaluable information on things like the fit, the materials used, the cut, etc.

Using the same sweater that we did above, here’s an example of a product description:

Here are a few specific things to look for:

What materials is the garment made of?

You can see this sweater is made 100% of Merino wool.

Was wool (specifically Merino wool) one of the materials you commonly found in your closet from step #3 above ?

What style/cut is the garment?

100% Merino wool and V-neck style sweater.

Do you own any V-neck sweaters or shirts? If not, can you see yourself wearing this style of garment?

How do you care for your garment?

Under this section, you’ll most frequently see machine wash or dry clean only.

Machine wash is obviously ideal. So, if it is dry clean only, be sure the item is worth it.

The additional stuff

In the product description area, you’ll also see anything outside the materials, cut and care that you might want to know about the item.

Really, this could be anything, but here are a few examples:

  1. The type of fly a pair of pants or shorts has (buttons, zipper, etc.)
  2. The type of buttons it has (snap or normal)
  3. That it has a water repellent exterior
  4. Etc.

Step 6: Check the return policy (and return shipping costs)

Perhaps the most important step to buying clothes online is checking, and fully understanding, the item's return policy.

Let’s look at the return policy for our Merino wool V-neck sweater:

When you’re looking at a return policy, there are a few things you need to know:

  1. How many days do you have to return the item?
  2. Can you open the package and try on the item?
  3. Will you get a refund or store credit?
  4. Who pays for return shipping, you or the website?
    1. If you have to pay for return shipping, how much is it?
  5. Are there any other fees associated with returning an item (such as a restocking fee)?


While this seems like a lot of questions, a reputable online store will have them all clearly outlined in their Return Policy.

With that, the vast majority of online stores will also have a live chat option. To make things easier on yourself, just copy and paste the above five questions into a chat window and let a representative give you a quick and clear set of answers.

Step 7: Know what items not to buy online

While it’s highly likely that you’ll get the right fit using the six steps above, there’s still one type of clothing I don't recommend buying online:

Fitted clothing (like a fitted suit or jacket).

As you know or can probably envision...

...these garments need to fit perfectly to look good. A perfect fit requires exact measurements, specific to that garment’s cut, fabric, style, etc..


You can always get things tailored... but unless you find an incredible deal on something fitted, I suggest you skip it.

In Conclusion

Shopping for clothes online doesn’t have to be difficult or stressful.

Follow our seven foolproof steps to buying clothes online, and you’ll get the right fit and the right items!


Do you have any questions on one of the steps above or any other tips for buying clothes online to share? Drop them in the comments section below!