I’m still debating with myself about the over the knee boots.  It’s now moved on from ‘should I get some?’ to ‘which do I get?’.  It’s a tricky one.  The choice rests between two Stuart Weitzman styles – the Stuart Weitzman Highland or the Stuart Weitzman 50/50.  Both over the knee but VERY different.  I actually could make an argument for both – which is the problem – because now I want both.  The Highland is long, sleek, heeled and sexy – definitely a going out boot, and the 50/50 is a low heeled boot, more practical looking, but still a gorgeous riding boot that could be worn during the day too.  My heart says the Highland, my head says the 50/50.

If I go for the 50/50 another multitude of decisions needs to be made – suede or leather, print or plain, and then what color? I love both the black suede and the topo suede.

Then look what arrived on the Bloomingdale’s site the other day!  This nubuck pair is divine – imagine them with bare, tanned legs and a dress.

So that’s what I did – imagined myself with OTK boots and a dress.  Fatal.  That vivid imagination of mine led me straight to the ASOS site.  ASOS are killing me.  They are my new go to site when I am on the hunt for something.

For me the critical features that a dress must have to be worn stylishly with OTK boots are:

1. Slightly loose or flowy – nothing tight – way too hoochy mama with boots – think Pretty Woman.

2. Not too dressy – for the same reasons as above – let the boots do the talking.

3. Don’t show too much skin up top – no boobs or cleavage for Pete’s sake.  We’re looking at the legs not the tits.

4. Slightly shorter than the top of the boots – let at least an inch of flesh show between the boots and dress, either bare legs or opaque tights.  If you wear tights – make sure they are a slightly lower denier or color from the boots – you want people to see where the boots end – they are thigh highs and supposed to be a little sexy! (again just not Pretty Woman style)

Okay those are the rules – fairly easy to follow and easy to apply.  All I did was search for ASOS brand black or grey dresses and here are the all the dresses that I now cannot live without.  Especially once I have my OTK boots – whichever pair I end up with.  If I procrastinate any longer they will be sold out.  These first few dresses are lovely casual dresses that contrast brilliantly with the decadence of thigh highs.

I love this dress – I’ve seen a few sweatshirts with similar print.  This would be perfect with suede Highlands.

I’ve just ordered this sweatshirt dress – again perfect for wearing with a dressy heeled boot – I love the juxtaposition of the two together.

This jersey nepi dress is the PERFECT shape as far as I am concerned for thigh highs.  Nothing too OTT about the dress – it’s all about the boots.

I love this skater dress for the same reasons.

Remember what I said about no flesh up top.  This dress takes it to the extreme – gorgeous with short hair or long hair in a high pony tail, with the boots of course.

Now this one bends the rules slightly – but there’s always one isn’t there?  With the flat 50/50s this would be perfect – here the top of the dress compensates for the lack of heel on the boots.

This crack print dress fell in the mix purely because I adore the print – very Mint Velvet.  A perfect party dress with high or low heeled OTK boots.

Finally a drop waisted dress.  Pretty, flirtatious and no hoochy mama in sight.

So now the conundrum – which boots is it to be?  Choosing the dress will be easy then no?

As I head off to dream about thigh high boots here’s what I’ve been wearing the past couple of days.

I bought these Steve Madden boots so long ago that at the time it completely escaped me what fabulous Marant tributes they are!

Boots – Steve Madden Carlsen (old) // Trousers – Zara (old) // Sweater – Off Duty sweater Boden // Coat – Mango

Jeans – H&M (old) // Tank – H&M (old) // Sweater – Zara // Boots – Isabel Marant pour H&M via eBay // Scarf – H&M (old) // Jacket – Zara

Related articles

• The Stuart Weitzman Highland Boot
• My boot obsession.
• Jeans and Jumpers.
• Dress down Friday.