Street Sneakers - How Do You Wear Them?!

Street sneakers. You know everyone else is wearing them, and you know you want to, but you are not convinced that you can do it, too.

Now first of all - YOU DON'T HAVE TO.

We don't all have to do what everyone else is doing - NOPE, we really don't.

But if you would like to give them a try and you think that a challenge is just what you need in your life right now - give it a go, why not! Just start with baby steps by cuffing your jean fabric as far away from the shoe as you can.


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Street sneakers are not going to be everyone's cup of tea, they are not going to float everyone's boat and even if you have jumped on board the street sneaker train, you may not be ready to wear them with a skirt - even harder still, a leather skirt.


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If you are wondering why I went for a bright white street sneaker, well it is because I don't own anything else in bright white, all of my whites are actually off white, ivory and light greys so they will always pop in comparison.

This means that nothing I own will ever match (or blend in with) my bright white street sneakers allowing them to stand out as the single statement feature on their own. So when popping into the shops to try on a pair for yourself, have a think about which colour would stand out the most against your wardrobe.

If you are going to do it - go all the way baby!


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  1. A&H Mickey Bomber Jacket
  2. FANE Urbanette
  3. Adidas print bomber
  4. Tan pencil skirt
  5. Warehouse Faux Leather Pencil Skirt
  6. Black sneakers
  7. White sneakers

Just a little hint when trying out those very masculine bomber jackets. Just pop a print tee underneath to break up the boxy boyish feel or buy your bomber jacket in a print which will do the same thing.

The video below will show you how different jackets behave, and why if you can only afford one jacket this season, grab a bomber jacket in a print or a boyfriend blazer in one of your best neutrals or a best colour.


Have you joined the Boss Course yet? Sign up on the wait list to be the first to know when it does! You can join the first to know group < HERE >.

If you are not ready to go out and buy a pair of street sneakers just yet or any boots for that matter, you may need to read my Ultimate Boots Guide first. BOOTS ARE EXPENSIVE!!!

Now, for those of you waiting for the next round of the Boss Course - can you please register by clicking here so that I can send you the link to come in on the next launch, thanks guys.

Got questions for Da Boss? Just leave a comment below.