How I Pair Shoes With My Outfit

I get asked quite often what shoes I wear with different outfits, so I thought I’d write a post on all my tips and tricks for pairing shoes with your outfit. I didn’t realise how many rules I had until I started writing this!

Boots are my new shoe obsession – although I’ve always loved an ankle boot. I wear them with skinny jeans for a casual everyday look or a wide leg trouser if I want to look a little more polished. I never pair them with a straight leg, unlike a flat pump which I think goes with a straighter trouser as well as a looser skirt. I recently bought a leopard print pair from Aldo, which are my go-to flats at the moment. I’ll wear them with skinny jeans and one of my new winter jumpers.

I don’t have any flat ankle boots, as I find they are difficult to style and pull off.  But I do love a flat knee-high pair of boots. I wear them with short skirts, dresses or skinny jeans usually. I would steer clear of long skirts/dresses with flat boots as I think this looks a bit frumpy on me.  In a way, a small heel on a knee-high boot is more versatile. I wear them with skinny jeans (but with a baggy top/jumper so it isn’t all too tight!),  and longer skirts and dresses. I would also wear them with a knee-length skirt, but probably nothing shorter than that for fear of looking a bit ‘Pretty Woman’!!  Everything is about balance, especially when it comes to hemlines and heels.

Lisa Comfort - How to Style Shoes

When it comes to skirts, it all depends on where they fall whether I’m to wear a heel, flat, over or below the knee shoe. I’m 5’6 and I want there to be a good ratio of skirt, leg and shoe, so I usually keep the rule: above the knee – longer boots, below the knee – shorter boots. However, if it’s a skirt like Lizzie for example, then the rules are out the window and I love pairing her with a pair of knee highs that overlap. Keeping to the rule, if it’s a maxi I’ll wear an ankle boot with it in the winter or maybe even a white lace-up pump – sometimes with tights too.

Lisa Comfort - How to Style Shoes

In the summer you won’t see me in short skirts, as I don’t like my knees. I tend to get my psoriasis here so like to cover it up. I wear a lot of maxis and will pair them with the ultimate dresser-downer, flip-flops, which I love the look of –  so boho chic.

When I want to elongate my legs I’ll go for a court or pump, ideally nude but I always avoid a shoe with an ankle strap when I want my legs to look longer. The strap interrupts the leg line and makes it look shorter.

Lisa Comfort - How to Style Shoes

I love colour pink as you know and have loads in my shoe collection. Last season I splurged on a pink pair of Brother Vellies which I love (they were in the sale but still around £200!). I find navy goes really well with them. If I want to dress down an outfit, I’ll go with tan as I find it more toned down than black. And if I want to dress it up, I really enjoy adding leopard print to my wardrobe, I just keep the rest of the outfit really simple and wouldn’t wear any other prints.

Lisa Comfort - How to Style Shoes