Thigh high boots have long been associated with Julia Roberts’ character in ‘Pretty Woman’ and while I would never mind being mistaken for her, (not gonna happen) ‘working girl’ looks will not be on my list of styles to channel in the immediate future! With this is mind, finding the right pair of thigh high boots is a very delicate operation. You may have noticed that celebs from Miranda Kerr to Theresa May – YES, the home secretary, have all been rocking this seasons must have footwear. The thing is, Theresa May carries them off well, so as long as you know how to wear them, there’s a style to suit everyone.

Theresa May and Miranda Kerr rocking the look.

We find the best and easiest way to wear thigh highs is with your most relaxed clothes, these boots do ALL the talking so the rest of your outfit can chill. Millie Mackintosh and Lily Aldridge, with her 3.1 Phillip Lim boots, nail it.


Millie Mackintosh and Lily Aldridge 

3.1 Phillip Lim boots £520 

Kate Hudson and Penelope Cruz wear a suede style which can make the look much softer. Get their look with these styles from Opening Ceremony and ASOS.

Kate Hudson and Penelope Cruz 


Opening Ceremony Boots £543 from and ASOS slouchy ‘Kayleigh’ boot with stud detail £75.

Kate Moss also fly’s the thigh boot flag for Stuart Weitzman’s new collection, which is available in a wide range of colours.


Kate Moss looking super glam. Stuart Weitzman boots £425

Whatever you do, make sure they’re a snug fit on the leg, these boots can make your pins seem endless and slim as long as you get the fit right. Get it wrong, and you will add unnecessary bulk.

Miley Cyrus has a tiny frame and these boots do nothing to flatter her, the lack of clothing is also a massive example of how NOT to wear thigh highs – even if you are a global superstar.


Christina Miliani and Miley Cyrus venturing into the ‘no go zone’.

We love RiRi and she does carry the look well with her body suit from her own collection at River Island, but it is bordering on fancy dress – sorry! If you did want to try this look may we suggest the simple addition of some opaque tights? It’s chilly out there at the moment!

RiRi on a night out with her thigh high numbers.

If your style is slightly tougher, take a leaf out of Gwen Stefani’s book and go for leather with a chunky heel against skinny jeans or combats for the ultimate in casual cool. We found a great version of Gwen’s from Topshop.


Gwen, as always looking fab and Topshop ‘Commander’ boots £150

For a completely vegan option without compromising on style, try Stella McCartney’s, perforated leather look, thigh high boots. Blake Lively strutted the red carpet in these at the beginning of the year and certainly made a statement. The really good news is that if you head over to Net-a-Porter, these exact boots are available to buy now and have been reduced from £715 to £429 a saving of 40%.


Blake Lively on the red carpet. Stella McCartney boots on the runway

Good luck venturing into thigh high territory and we’d love it if you tweeted us your pictures of you in your boots and how you’ve styled yourselves @BangTidyStyling .

Jemma x