Online Shopping Tips for Men (How to Buy Clothes Like a Pro)

Do you shop for clothes online? Some guys love buying clothes online, while other guys hate it with a passion.

Here's what I believe:

In order to be a stylish shorter man, you need to be willing to shop for clothes online.

In fact, you have to be really good at it.

If you think online shopping is a frustrating experience, or if you refuse to do it at all, this post is for you.

The truth is, buying clothes online can save you time and money. But you might not believe me. You might be thinking:

What if what I buy doesn't fit?

I can't try it on before I buy…

It's a pain to return stuff I don't like.

I hate paying for shipping.

How do I know my size?

These are all valid concerns, but they shouldn't hold you back from buying your clothes online. In fact, these potential pitfalls can be avoided, and I'm going to teach you how.

TRENDING: How to Save Money on Clothes 

I'm an avid online shopper, and I buy pretty much all of my clothes online. So I've become really good at online shopping.

I've learned a few tricks over the years, and right now I'm going to reveal six strategies I use to make shopping online a positive and rewarding experience.

Tip #1: Buy stuff you know and love (and that fits)

This one is no brainer. If you've already tried something on, and you know you like it (it fits well and goes with the rest of your wardrobe), it's safe to buy it online.

For example, if you've worn out a pair of chinos and just need a fresh replacement, or maybe you just want to add another pair in a different color to your wardrobe.

Skip the store and buy it online.

I do this all the time with shoes. I know that any Cole Haan shoe in size 7.5 will fit me perfectly, so I can buy a new pair online with confidence.

Tip #2: Don't buy anything that can't be returned

Sometimes you'll come across these clearance deals where you can get 40-80% off clothing and accessories, but always read the fine print.

Often times, these clearance deals are for “final sale” items, which means whatever you buy can't be returned – even if it doesn't fit right.

Unless you're absolutely positive that you won't need to make a return (see tip #1), don't buy final sale items.

Tip #3: Shop at stores that offer free shipping AND returns

Many clothing retailers, especially the big ones, offer free shipping and free returns these days. In fact, you'll often find a pre-paid return label in the box.

At the very least, try to buy from places that offer free shipping. And keep in mind, while some stores offer free shipping all the time, many use it as a promotion.

For example, J. Crew regularly offers “today only” free shipping. So if you have something from them on your wish list, but you don't need it right away, you can wait for one of these free shipping deals before you buy it.

Tip #4: Wait for sales

There are amazing sales going on all throughout the year. In fact, for major brands like J. Crew or Nordstrom, you can be fairly certain that, on any given day, some sort of sale is going on.

If you can't find a sale listed on the actual website (check the “bar” at the top of the site), you should use Google to find any active promo codes.

UPDATE: Just heard about this Chrome extension called Honey that automatically looks for working discount codes while you're shopping (thanks, Alex).

Also, most online shops have a permanent “Sale” page where they keep a running list of discounted items.

If you're patient, it's possible to never pay full retail these days!

Tip #5: Buy multiple versions, and return whatever doesn't fit

Not sure if you're a S or XS? Trying a new shoe brand that might run big? No problem! Just order two or three sizes, and return whatever doesn't fit.

Whether or not shipping is free, ordering multiple items won't make shipping more expensive, so there's really no downside to this strategy (other than having to make the return).

I do this all the time when I'm ordering from big companies that offer free shipping and returns, like Zappos and Amazon. It's especially helpful with shoes and boots.

You can do this with colors too. Say you're buying a t-shirt. You should order three or four different colors and keep the ones you like best.

Tip #6: Try shopping secondhand before buying new

I love going to secondhand stores and thrift shops, mostly for the thrill of the hunt. Every now and then I'll come away with a gem, like these Cole Haan loafers.

But most trips to the thrift store are just for fun. I rarely find anything worth buying.

It's a different story when you're shopping online, though. You have access to the biggest secondhand clothing shops in the world, right at your fingertips and from the comfort of your living room.

These shops are good for browsing, but you should definitely do a quick search before buying something new, especially if it's an expensive “investment” piece.

Here's a good list of virtual secondhand clothing shops:

• Grailed (my personal favorite)
• eBay
• StyleForum
• Ask Andy About Clothes
• Dappered Threads

There are probably other places to buy and sell clothes online, but these are the big ones that are worth checking out.

BONUS TIP: Adopt the right mindset, and get used to it.

Dressing well isn't easy. If it was, everyone would do it, which is why the vast majority of men don't dress well.

It's not convenient to get a haircut every three weeks or go to the dry cleaner regularly. It takes extra effort to get your clothes tailored and to drive to the post office to return something you bought online.

But it's worth it. So if you're the kind of guy who thinks shopping online is too risky and too much of a hassle, here's my challenge to you:

Man up, and get used to it. Make it part of your weekly or monthly routine. It's all a means to an end, and that end is looking good and feeling great.

Do you shopping for clothes online? Leave a comment below!