This site contains affiliate links to products. We may receive a commission for purchases made through these links. Learn more

The 15 Coolest Boots Under £100

The 15 Coolest Boots Under £100

The 15 Coolest Boots Under £100

You're right. You're definitely too old to still be wearing those tatty Converse to the office. 

As the February slush soaks into your socks, you're probably regretting your young-at-heart footwear choice with renewed passion. Not to worry, we've taken the effort out of searching for a hardy upgrade by putting together a selection of some of the best-looking boots you can buy for £100. 

From formal Chelsea boots to rugged hiking options, there'll be an option amongst the following 15 to suit your needs. 

Stargent boot by Kickers

French label Kickers has taken inspiration from the military for its prim and proper Chukka boot. A mid-ankle finish with a cavernous cleated outsole, there's something a bit 70s punk about these.


Earthkeepers Fulk Leather Boots by Timberland

The rugged, hard-wearing endurance of a boot, married to the casual, clean lines of a hi-top. While that might sound like a mess on paper, Timberland has managed to pull it off in quite some style. Layered in nubuck and full-grain leather, the Fulk urban boot uses a heap of recycled materials, including old plastic bottles in its laces.



Credited to Queen Victoria's shoemaker J. Sparkes-Hall, the Chelsea boot design hasn't changed all that much since 1851. Clarks have given it a modern polish with a moisture-wicking footbed sitting beneath the hairsheep inner lining, and splash of colour on the pull loop. 


Peter Werth tan winstone boots

Taking some design nods from classic riding boots, Peter Worth's Winstone boot manages to pull off an unconventional blend of a smooth leather toe and heel with a layered suede ankle. Best worn on the back of a classic British motorcycle, rattling down a country lane. Or the pub. Either really. 


Union Street Too Plain Toe Chukka by Rockport

By virtue of some clever technology from borrowed from adidas, Rockport makes some of the most comfortable boots you're ever likely to sink your feet into. The adiPrene cushioning on the inside of this Chukka helps protect your heel from impact shocks, meaning you glide rather than clomp. 


Jack & Jones Boots

We're not sure how, but Danish brand Jack & Jones has managed to construct a superb, vintage-styled leather boot without charging you the earth to own a pair. Metalwork on the eyelets and hooks add yet more ruggedness to these traditional worker boots, with a chunky rubber sole finishing off the design. 


Chilkat II boots by The North Face

If you're actually looking to cover some miles in your boots, best skip over the others in our selection in favour of these solid beasts from The North Face. Totally water proof, packed with 200g of insulating materials and sporting the brand's toughened "Winter Grip" soles, these will keep your feet in top shape at temperatures as low as -32 degrees.


Asos Chelsea Boots

You don't have to break the bank to get your hands on some proper leather footwear - as proved by these affordable Chelsea boots by ASOS. Ideal for that new grey suit you bought in the sales or for dressing up a pair of jeans (so long as they aren't black). 


Dr Martens Classic

An icon. With its imposing row of eight eyelets, hardened black leather and trademark yellow stitching, the classic Dr Marten won't be for everyone, but there are few more striking models out there. 


LONGLEAT by Base London

The embodiment of smart/casual, the Longleat by Base London takes its cues from the styling of a worker boot and formal shoe. You're guaranteed a close fit - in addition to the laces, there's a zip fastener on the side and an ankle buckle. Apparently they ran out of room for the velcro straps.


Duncan Fold Boot at Topman

This textile offering from Topman sneaks a fold-down layer into its ankle, allowing you to change up the leather-look to reveal a quilted fabric underneath. It also adds some much needed padding to help keep you insulated from the ankle down. 


Double zip boot by Next

Neat and simple, there's no clutter to these double zipped boots from Next. Rather than having to do battle with a shoe horn, zips on both sides of the ankle open up the boot for an easy job of sliding it on over some thicker socks.



There's a weathered, worn-in quality to these Chukka's from River Island - a burnished finish, that says you've been some interesting places. Places like River Island. But seriously, they're a superb replacement for those trainers you've been meaning to ditch for the past few years.


Founder Boot by Caterpillar

There's something effortlessly masculine about a Caterpillar boot. The "everyday" model in their line up, the Founder mixes a hardy leather and nylon construction with a chunky-grip outsole. Best not wear these to any building sites though - there's no steel toe cap in this lightweight design.


Casual Brogue Boot by Linea

"What I'm looking for is a boot that's a bit like my brogues", would be an annoying request in any shoe shop that doesn't stock a pair of these casual boots from Linea. Mixing the classic detailing of a brogue with the solid build of a boot, with the right trousers you can pass these off as a formal shoe or a casual boot.