British Model Oliver Cheshire: Steal His Style

At 29 years old, it is safe to say that model Oliver Cheshire has done incredibly well for himself.

The photogenic personality began his successful modelling career at the young age of 15, after being scouted by top agency Select Model Management at Clothes Show Live.

His early campaigns saw the model working with high-end brands such as Calvin Klein Jeans, Dolce & Gabbana and Missoni.

As he became better known in the modelling industry, Oliver began to change things up, shooting successful campaigns with top-end designers as well as high-street brands including Marks & Spencer and Superdry.

To help inspire others, and document his favourite looks, the modelling star runs his own blog website named ‘I Wear The Trousers’, frequently posting his everyday outfit choices.

The model is also known for his well-documented long-term relationship with pop singer Pixie Lott, with the pair linked together since 2010.

He may be best known for his dazzling chiseled looks, but it’s his smart, dapper sense of style that has us hooked!

Keep reading to uncover some of the hunk’s best eyewear looks to date!


Colour Block


Talk about keeping things cool – we’re loving this icy shot of Oliver, pictured with his girlfriend Pixie Lott, on holiday somewhere chilly.

However, Oliver keeps his outfit warm yet stylish with a mustard turtleneck knit, styled with some casual black trousers. Burgundy coloured lace up boots complete the look, as well as a thick royal blue coat and a pair of great specs.

Steal Oliver’s look with these similar Ray-Ban RB3507 CLUBMASTER ALUMINIUM sunnies from us here at SelectSpecs!



Geek Chic


We are loving this outfit choice here from Mr Cheshire! The model keeps things cool and casual with this black turtleneck and grey suede jacket, while a dazzling watch on his wrist adds a touch of luxury.

Oliver also smartens things up with some awesome geeky specs!

Take a look at these similar Savannah 2444 – Black glasses to complete your inspired look.

Savannah 2444 – Black


Casual Attire


This is a great outfit from Oliver, consisting of a dark blue denim shirt and black jeans – very trendy! He has styled it up with a suede and shearling number, which just gives him all the style points.

The model makes the look a little more A-list too with the addition of these fabulous dark shades. Steal Oliver’s look with this pair of similar William Morris London SU10006 sunnies from us.

William Morris London SU10006


Slick in Sportswear


We are loving this look from Oliver! In this Insta shot, the model sports a short sleeved monochrome striped shirt, paired with some casual red tracksuit style bottoms. Slick black boots and some stylish shades finish off the look well, giving the outfit more of a formal vibe.

Take a look at these Oakley OO9013 FROGSKINS (Polarized) sunnies for a cool accessory option.

Oakley OO9013 FROGSKINS (Polarized)


Off-Duty Style


This is definitely more of a chilled look from Oliver! During a trip to the French capital, the model rocked a simple outfit consisting of a mottled tee and black skinny jeans. He styled the look with some blush pink trainers, which adds a sporty vibe to the outfit.

Other accessories include a Louis Vuitton bag and some blacked out sunnies, giving him that true A-list vibe.

Take a look at these similar Carrera CARRERA 6000 (Camouflage) shades, courtesy of us.

Carrera CARRERA 6000 (Camouflage)


If you loved this model inspired post, make sure to take a look at this similar post on ‘Top Male Model: Jordan Barrett‘.

Tag #SelectSpecsSelfie for a chance to be featured!