How to Put on Chelsea Boots (Step‑by‑Step Guide)

Written by Dan Simiele

Chelsea boots are one of those rare shoes that look sharp, feel effortless, and somehow work with just about everything. But if you’ve ever tried slipping on a brand-new pair, you’ll know they can feel like they’re testing your patience before you even leave the house.

The good news? Chelsea boots are built to last, and once you know the right way to put them on, they’ll slide on smooth and keep their shape for years. Here’s your step-by-step guide to putting on Chelsea boots and wearing them right.

 

 

Step 1: Loosen Them Up First

When you’re fresh out of the box, Chelsea boots can feel snug. That’s because they’re designed with a close silhouette for a sleek look. Give the elastic gussets a light stretch with your hands (don’t go Hulk on them, just a little pull) before sliding your foot in.

Check out our Men’s Chelsea Boots collection

 

 

Step 2: Use the Pull Tabs

Chelsea boots are famous for their pull tabs. They’re not just decoration, they’re your best mate. Hold onto both tabs while easing your foot into the boot. This keeps the leather looking sharp and saves you from crushing the heel counter.


Step 3: Slip, Don’t Shove

Never force your foot in like you’re kicking off a sprint. Instead, angle your foot slightly and let the gussets do the work. A little wiggle, a little patience, and they’ll slip right in.


Step 4: Wear the Right Socks

Pro move: pair your Chelseas with slim socks, especially the first few wears. Chunky socks can make slipping in harder and stretch out the gussets faster. Once the leather moulds to your foot, you can switch it up.

 

 

Step 5: Break Them In

Wearing Chelsea boots gets better with time. The first few outings might feel snug, but the Premium First Grade leather will soften and shape to you. Think of it as the boots getting to know you. After a week or two, it’s like they were made for you.

 

 

Step 6: Style Them with Confidence

Now that you know how to put on Chelsea boots, let’s talk about wearing them.

  • Leather Chelseas: pair with jeans, tailored trousers, or a suit for work-to-weekend sharpness.

  • Suede Chelseas: casual perfection with chinos or rolled denim.

  • Black Chelseas: the wildcard, ready for weddings, nights out, or going full rebel.

Find your perfect pair:


 

Adventure Calls

Putting on Chelsea boots isn’t complicated once you’ve got the technique. Use the pull tabs, take your time, and let the leather shape to your stride. Soon enough, they’ll slip on like second skin.

So, next time you’re gearing up for the day, remember: Chelsea boots aren’t just footwear. They’re your ticket to walking out the door feeling unstoppable.