Flip flops or boots?

Angie Says:
Help Ali! I see people wearing flip flops still .... and the boots are already out. In fact, the stores are full of them. When and how are we supposed to be wearing boots? Should we be buying them, wearing them, or both?

Ali Says:
The shoulder season (the transition from fall to winter) creates wardrobe challenges for even the savviest fashionista. Take a look out the window for proof that no one is really sure exactly what to wear at this time of year. Today’s debate: flip flops vs fall boots. I’d say they are both okay. Depending on the day, depending on your look, the unpredictable weather means you can go with whichever you prefer. Here’s how:

First let me reiterate that we are not talking about one dollar rubber shower shoes one picks up at the discount store. Rather, we are referring to actual footwear that has a flat sole and a narrow strap typically between your big toe and the rest of your toes.
At this time of year the clock is running out on days that one can actually get away with wearing flip flops (or open toed shoes of any kind). Soon it will simply be too cold. Avoid wearing them with shorts and skirts as you run the risk of looking over exposed (or feeling overexposed which leads to goose bumpy skin which is never in style!). If you aren’t ready to let go, make sure you balance your ‘skimpy’ shoes with warmer layers on top. Think jeans and a long sleeve top with possibly a pashmina.

Boots are one of my FAVOURITE things to collect. Leather, suede, tall short, black, brown, beige, green navy, I cannot seem to get enough and I feel no need to justify! A great pair of boots is always in style. That being said, it’s tough to make a pair of boots work during the hot summer months. Now that the temperature is markedly cooler it’s open season to bust out your boots and get struttin! Take my advice from above and do the opposite. Temper your excitement by pairing your ‘heavy’ boots with something lighter on top. Boots look awesome with dresses (in denim, or knit as opposed to a cotton sundress), capris, or even shorts (in heavier fabrics like wool). Even though our winter season can seem too insufferably long, I always take solace in the fact that we have the perfect excuse to buy more and wear more boots. Game on!!