How To Dress Stylish: Breaking Out Of Your Style Rut and Trying New Trends

by Barron Cuadro  |  in Casual Style

It’s always smart to build a wardrobe that’s lean and versatile with your basics in neutral colors. That makes looking sharp easy since everything looks good together.

But sometimes you might get bored with a simple wardrobe and wanna switch it up!

So today we’re gonna go over 5 quick tips that will help you break out of your “same outfit, different day” rut, try new trends, and learn how to dress stylish.

Check out the video!

I put together a quick video on these 5 tips on how to dress stylish. Check it out below (and make sure to subscribe to Effortless Gent on YouTube!)

Thanks to our friends at Menlo Club for partnering with us for this article.

They’re offering a sweet deal to all EG readers: 50% off your first month’s box + a free pair of shades (just in time for summer)! Just use code GENT to claim that deal.


Let’s get to it! Here’s How To Dress Stylish:

Tip #1: Get Inspiration And Find Good Style Examples (3 tips in one)

Start by getting inspired. No, you don’t have to head downtown and people watch for hours on end. Just hop on Pinterest or Lookastic to find outfit and styling ideas.

Say you’re thinking about getting a new pair of tan chelsea boots but aren’t sure what you could wear them with.

Search “tan chelsea boots” on these sites (here’s an example) and check out the photos other guys have shared. You’ll see tons of examples and can definitely find something that fits your personal style.

From there, use Shopstyle to find the right item for you.

This site is a great way to narrow down your options. In the example of tan chelsea boots, you can search for them, adjust your price range, and even choose the exact color you want (See what I mean here).

Find a good deal on a quality product and bam, your new boots are on their way.

Speaking of tan chelseas, these ones are my favorites at the moment.

Tip #2: Buy One Piece or One Look At A Time

This is all about exercising self control. Yes, trendy and stylish looks can be fun.

Incorporating them into your outfit is a smart way to balance your classic approach with updated style, but go overboard and you’ll dilute your classic pieces with too much trendy stuff.

This approach is best because it…

  • Saves you money
  • Builds your confidence with new pieces
  • Won’t overwhelm you with too many options in your closet

And you’ll have other chances to pick up cool pieces. Start with one, build that confidence and understanding of how these new things look on you, and then move on to your next piece, and your next piece after that.

Tip #3: Buy Affordably At First So You Can Try Different Looks

Buying high quality, higher cost items is worth it. But not when you’re first trying out a brand new style.

Save your money for those items you know you love, you know you’ll wear all the time, and you know you’ll still be wearing years from now.

For the trendy pieces that you add to your wardrobe, focus on affordability.

That way you don’t blow your fashion budget on a new shirt or pair of shoes that you wind up hating and stuffing in the clothes cemetery at the back of your closet.

This is where online shops / subscription boxes like Menlo Club come into play. You get to try new things affordably, and you don’t have to think about it.

Check out Menlo Club here (Sign up and get 50% off your first month + a free pair of sunglasses with code GENT)

Tip #4: “Test Drive” Your New Stuff First

It takes time to get comfortable in something new. You won’t be as confident and it can feel downright awkward. So don’t head out to an important business meeting, big event, or high pressure appointment in your new items.

Test drive something new by wearing it around the house first.

Get used to wearing it, seeing yourself in the mirror, and feeling natural. Take a day, or a week, or however long is necessary to feel confident before you wear your new digs out in the real world.

From there, keep it low pressure.

Wear your new items while you’re out running errands or grocery shopping. This slowly builds your confidence and helps you feel comfortable with what you’re wearing.

Tip #5: Mix New Pieces With Your Current Wardrobe To Freshen Up Your Go-To Outfits

This has several benefits.

  • You’ll breathe fresh life into your old items by mixing them with new pieces you love,
  • You’ll discover new outfits and color matching options that you hadn’t tried before,
  • And you’ll feel less awkward about your new clothes since you’re pairing them with tried and true classics you’ve had for years.

Soon enough those new pieces won’t be new at all. They’ll work their way into your everyday wardrobe and your style will benefit as a result.

What are you looking forward to trying with your style?

I hope these tips help you learn how to dress stylish and break out of your style rut! Let me know what you found most helpful in the comments below.

Make sure to check out Menlo Club and take advantage of the sweet deal they’re offering all EG readers: 50% off your first month’s box + a free pair of shades.

You can also buy anything you see on the site. And as a member, you’ll get 25% off and free shipping!

Just use code GENT so you get 1/2 off. Learn more about Menlo Club »

I wish you the best of luck as you try new trends, colors, or whatever you’re inspired to test out with your personal style!