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My Best Tips for Shopping Online

I’ve been hearing from our community about how challenging they find shopping online for clothes.

So today, I thought I would map out some of my best tips to help you navigate the world of e-commerce, so you keep more of what you buy and save yourself trips to the post office. 

Our Current Situation

Retailers and malls were experiencing dwindling sales and low foot traffic long before the pandemic. 

Many of the stores and shopping destinations currently on the cusp of never recovering from our economy’s freezing were in dire straits before this because they didn’t adapt to the changing world.

Shoppers have been underwhelmed for a long time. 

Now, all retailers are going to have to overhaul how they do business.

The aspects that made shopping fun and convenient are missing.  And as long as there are surges and masks-wearing, a lot of people will avoid the mall and stores altogether.

Today, nothing is easy or enjoyable about in-person shopping. Many retailers still have dressing rooms closed; and even if you could go into a dressing room, there is limited inventory and sizes.

Before 2020 many departments and specialty stores moved their petite and plus sizes online or greatly reduced their square footage. 

And customer service is non-existent.

Without a pleasant in-store experience, retailers have to figure out how to maintain sales, so they will incentivize us to shop online, like deep discounts, bonuses, and free shipping.

But that brings along its own set of frustrations. So let’s net out how to do it well, so you save time, money, and sanity.

My Best Tips for Shopping Online

My Best Tips for Shopping Online

Personally, I’ve never enjoyed shopping in person. It’s online only for me, all the way. 

Here are some of the ways I navigate it. 

Figure Out Your Personal Style

Knowing what you like, what you don’t like, and what you’re looking for is the biggest game changer when it comes to shopping online. 

Take some time to discover your personal style. I go into detail on how to do that here

If you don’t know your style, how in the world are you going to see items you like?

Create an inspiration board. I use Pinterest, and update it frequently.

Then, when you are considering a purchase, ask yourself if that item will you help you create your ideal style.

Know Your Measurements

The long held belief by almost all of us that we are a certain size is pointless. I can wear anywhere from a medium to a x-large, and an 8 to a 12 – all depending on the brand.

You need to take your measurements and have them on hand to compare to the size guide provided on store sites. I keep mine in the notes app on my phone. You want to have your shoulder, bust, waist, hips and inseam. 

Check Retailers Sizing Guide

Next, you must refer to each retailer’s size guide before adding anything to your cart. Every single one is different. The reason is that sizes are not regulated in the retail industry. Manufacturers can (and do) create their own size scale with no rhyme or reason.

Below, I captured the size charts from three of our most popular retailers: Old Navy, J.Crew, and Banana Republic.

Size Charts for J.Crew, Banana Republic, and Old Navy

Let’s say your bust measures at 38″.

You would be a large in Old Navy and a Medium in J.Crew and Banana Republic. That’s a full size difference (which hold true in real life) and these brands are all under the same ownership. 

The discrepancy is even more drastic with brands that target different demographics – for example, I would swim in a size 10 suit from Talbots, but it would be tight in Theory. 

And if you are in the States, but like UK brands, remember their sizing is completely different than ours. 

Read Reviews

Many retailers offer customer reviews that provide both a star rating AND comments.

If you see something you like with a low star rating, be sure to read the accompanying comments.

Often, customers write poor reviews because of shipping issues, or matters of personal tastes that have nothing to do with the fit and quality of a product.

Check the Return Policy

As the retail landscape changes, I can guarantee return policies will become more generous, and additional conveniences will be offered, like prepaid shipping labels, pick up, etc. Just give it some time.

However, it’s still important to check.

Not long ago, I made an impulse buy off of Instagram to try a brand that kept showing up in my feed.

By the time I opened the package, a few days after receiving it, I had pretty much missed the window to send it back. They had a ten-day return period with convoluted requirements for return and refunds. 

It was so much extra work I ended up eating the order and learned a valuable lesson.

What (and Who) to Avoid

Speaking of what to avoid, proceed with caution when it comes to “social media brands.” These are brands like the above example that focus their marketing entirely on platforms like Facebook and Instagram.

Their shipping times tend to be so long you forget you even placed an order and have impossible return periods. More so, they’re not transparent about manufacturing practices.

If you see a product or brand you’d like to try, first do a quick Google search to find as much information as possible.

Always read their “about” page. If they don’t have one, it doesn’t sound professional or they don’t provide key information like a customer service number or address, avoid it. 

Wear it Three Ways 

Follow the same guidelines online that we recommend for in store purchases. This is where I find online shopping incredibly helpful. It’s just you shopping! 

Before you pull the trigger on a purchase, ask yourself a few questions:

Do I LOVE it (assuming it fits the way you hope)? 

If it’s a mix and match item, can you wear it at least two, maybe three ways? 

If it’s a better basic, how frequently will you reach for it? 

Depending on the price, could you benefit from having more than one?

What’s nice about online shopping is you have no pressure.

You can toggle back and forth between your Pinterest boards and your shopping cart. You can search for discount codes, or options at different stores.

You can walk away for a minute without feeling bad about wasting someones time. 

Online shopping can be incredibly efficient and fun with just a little pre-work!

Them, when the items come in, you can spend time trying them on in the comfort of your home, with the pieces you already have to see what they will look like in your real life wardrobe!

Find Trusted Resources

One of my goals here at The Well Dressed Life is to take the stress out of shopping for our community as much as possible. 

Our daily posts are designed to help sort through retail “clutter” and only feature pieces that will fit into a classic, modern wardrobe. 

And you can visit our Facebook Group to get updates, ask questions and get feedback. 

Finally, I recently set up my Like to Know it page, an app that helps you “shop” some of your favorite influencers. If you are on the app, you can follow me here. 

My Best Tips for Shopping Online

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Thursday 26th of January 2023

It's so true that on-line shopping is the best!!! I just about only shop on-line except for purses, shoes, accessories and fine jewelry!!!! Being disabled has affected my decision to shop almost exclusively on-line!!! I'm simply unable physically to shop the stores as I once did!!! I do really enjoy shopping for fine accessories!!!

Vicki Friedland Coss

Wednesday 26th of January 2022

Thanks for this good information. I wear petite sizes and since 2020 they are nowhere to be found in stores. Initially I was upset about it, but now I can really say that I prefer shopping online. There are 2 sites, Old Navy and the Loft where I know I can find great sales and reasonably priced on trend petite clothing. They have easy return policies too. I have also explored Short Story, a shopping service for petites. I have had reasonable results. Sometimes you just have to let go of the old ways of doing things and explore the new!

Megan Kristel

Thursday 27th of January 2022

Other good petite options are at Nordstrom, Banana Republic has a LOVELY selection and Talbots for basics.


Friday 21st of January 2022

I just can’t get through your posts anymore because of SO. MANY. ADS. Seriously, it’s awful. Please consider mobile readability/usability. Better yet, try it on your mobile device first for a firsthand user experience. It damages your brand.

Megan Kristel

Saturday 22nd of January 2022

This is a free website, running ads is the only way we are able to generate a regular income. There is no site without them.


Wednesday 19th of January 2022

My only problem with online shopping, and maybe you have some tips, is quality. How can you tell the quality is good just by looking at something online?

Megan Kristel

Wednesday 19th of January 2022

You can't. You have to read reviews, shop stores and brands you know and already wear, find trusted online resources like our site that vet products for you. It's still a chance you won't like it, but with a little bit of work, those buys will be rare.


Tuesday 18th of January 2022

Thanks for the tips! I've been doing a lot of online shopping recently with varying results. Do you have any thoughts on the "True Fit" recommendations? I ordered a jacket from Talbots using their size charts and it was huge on me. When I looked at the True Fit recommendation, I should have ordered 2 sizes down.

Megan Kristel

Wednesday 19th of January 2022

I'm not sure. Talbot's in particular is notorious for running full sizes large so in that case, yes. I like reader reviews so much more, maybe the answer is using a combination of the two?

Cathy Johnson

Tuesday 18th of January 2022

I always look forward to your posts, read them start to finish and find this one to be most helpful. There is always a nugget of information to make life easier. Thank you!! I order on line a lot but only keep about 50%, I will use these tips and hopefully have better success.

Megan Kristel

Wednesday 19th of January 2022

Thanks so much Cathy!!


Tuesday 18th of January 2022

Thank you for this helpful post. I wish more retailers provided garment measurements. That would make online shopping so much easier.


Tuesday 18th of January 2022

I have a question. I’m a large busted woman of 71. Do I measure my bust size without a bra for support or with one. Thank you.

Megan Kristel

Tuesday 18th of January 2022

I would measure wearing the bra you typically wear. :)


Wednesday 10th of March 2021

I did purchase several items from stores that I have always found what I liked and the fit was perfect However my online purchases were not as successful. I don’t know why but sizes I usually fit in and arrived and were either toot small or too big. It was frustrating. I should have read the comments from others and figured out what size I should be purchasing g. Thank you for this guideline.


Tuesday 9th of March 2021

I order on-line and prefer it this way. I am disabled and find walking around a mall very difficult and a frustrating event. I wear women's clothing and in-store options are few. I order from a few catalogs. I know their fabrics and fit plus I find soooo many more clothing options. I've made it a point to do business with businesses that meet my need and want my business!


Tuesday 9th of March 2021

I would add to all the above, to check for how to care for the clothing item. I've run into the occasional label which provides no care information online. Dry cleaning is a deal breaker for me for most things, and I won't order items that don't provide this information.

Linda M

Tuesday 9th of March 2021

I do most of my shopping on line, and did so before the pandemic, because plus size options are better in cyberspace. I’ve found I buy most of my clothing from 3-4 retailers, and because I do this, I have a good idea of how the items will fit based on the pictures and reviews. I avoid retailers who charge for shipping on a return. With the original charges, that can amount to a $20 try on. Also, if you find you like a retailer, you are likely to buy enough to get free shipping, as, for example, I do on any purchase made at Macy’s. Another good tip is to sign up to be whatever the brand calls its “insider” group. That usually is free to do and can result in free shipping. Finally, if you call the bricks and mortar store, they can place your order and the shipping is free to your home. I do this often through my local Talbots.


Tuesday 9th of March 2021

Thanks for such an informative post! I miss regular in store shopping- it’s been such a big part of my life that doing it all online is just not as fun! BUT- I can adapt and your guidelines are so helpful. I did see Kohl’s now carries LandsEnd not sure if you can return online LandsEnd orders to Kohl’s or not.

Jocelyn Reid

Tuesday 9th of March 2021

Unfortunately, you can only return Lands End items to Kohl's if you purchased them through the Kohl's website. Otherwise, they either have to be mailed back or returned to a Land's End store


Tuesday 9th of March 2021

Unfortunately the fabrics never look as good in person as they do on the websites. I'm usually disappointed with online purchases.


Tuesday 9th of March 2021

Thank you Megan...very helpful! I especially like your tip to keep personal measurements in “notes” on your device. I miss the old days of social shopping but I am adjusting.


Tuesday 28th of April 2020

Great article! I must add, the measurements aren’t correct on the charts, my waist measurements say i should wear a 6-8 in the waist of a fit and flare dress style, but 4 actually fit, in Talbots, Tommy Hilfiger, Anne Klein, Gal Meets Glam, and Boden. I also have from Target their plain white cotton shirt in both small AND medium, the measurements are exactly the same. If stores really want our business they need to actually measure the finished garments, instead of a size chart, it also addresses how tight or loose each person wants their fit to be on them. I noticed Uniglo gives garment measurements, and jeans on Nordstrom, but the “ size charts” seem outdated to me, in the world of online shopping.

Kendra McGuire

Monday 27th of April 2020

Megan - this is so thoughtful and helpful! I think you have captured our current approach to shopping and what possibly lies ahead. Love your blog! Thank you!!


Monday 27th of April 2020

Great article. I agree with Rita on the scam companies out of China. I try to google the company name and find out where the item is coming from. I have had the same problem when ordering on Amazon. Try and find out where the company is located that you are buying from. Megan thank you for the great information that you are providing.


Monday 27th of April 2020

Thank you for this very helpful information especially the “Who and What to Avoid” section. There is a scam company out of China with popup ads of beautiful unique clothes. Most of their ads are stolen photos of clothing sold by reputable companies like Sundance Catalog and other specialty sites. The scam company changes its name frequently to mislead people. Beware of the popup ads of clothes with prices that look too good to be true!!!! Thank you for your many well thought out and informative posts. Your blog is the BEST!!!!


Monday 27th of April 2020

Thanks Megan for the helpful hints for online shopping. Your post is very timely given that yesterday I was totally frustrated with Kohl's and how they handle returns. I'm generally not a Kohl's shopper for women's clothes, but due to being home and numerous ads inundating my email, I decided to order some items from Kohl's. They didn't work out and need to send them back. Well, Kohl's return policy is return to the store or your on your own for shipping. They don't even give you one of those pre paid labels that they would charge a fee for like some other stores do. So, given I am not going to the post office or UPS or waiting until the store opens in a few months, I had to get a box, weigh the box, measure the box and figure out how much it would be through UPS. Then pay and print the label and finally put it out for the UPS guy to take. All that said, beware of the Kohl's returns.


Monday 27th of April 2020

Wonderful insight! I'll have to make a checklist and keep it next tu o my computer. For those items with the extended return dates, I add a reminder/appointment in my calendar. It is especially handy for the cosmetic items that give you 60 days satisfaction guarantee. It also reminds that I can throw away the box the item came in if I'm not going to return it.