Transitional Dressing: Make Your Wardrobe Work

We’ve officially reached that awkward time of the year where wardrobe dilemmas are becoming a daily occurrence. Summer’s not quite over just yet but the weather can’t make up it’s mind (here in the LOVE ALICE office we’ve usually got the heater running in the morning and by the afternoon we’re taking breaks to stand outside and bask in the sun) and our outfit decisions are only getting harder with the temperature being so temperamental.

If you, too, find yourself lost every morning wondering just what the heck you’re supposed to wear, then have no fear! We’ve got you covered with staple pieces that will work come rain or shine.

Midi Skirts

The favoured length of 2020, midi skirts are still highly sought after — and for good reason! They’re just so versatile; pair with a slouchy tee and trainers for a dressed down look, or toughen it up with a pair of stompy boots, and throw a cozy jumper on top when it gets a bit chilly. Or, if you have a patterned midi dress lying around, you can still get the look with the tried and tested fake sweater tuck.

Depending on what you pair them with, midi skirts can go from hot to cold and day to night effortlessly. Try this tan wool pencil skirt by Christian Dior with a structured blouse for the office or trainers and an oversized knit for the weekend, or team this swishy layered black and gold skirt from Alice & Olivia with chunky boots and a leather jacket for an edgier look.

Jumpers & Jackets

Thin knits are your best friend at this time of year. Not only are they soft and cosy, but they’re perfect for layering either over a dress or skirt as above or under a jacket when it gets chillier. A plain coloured cashmere cable knit will last you well into the winter, while leopard print (practically considered a neutral at this point) can be casual with jeans or a little more dressed up with black cigarette trousers and heels.

As for jackets, they’re no longer solely an office staple — a bright, lightweight vintage Jacques Vert blazer can work in casual settings too when paired with a plain t-shirt and comfy jeans while denim jackets, like this Helmut Lang biker jacket, are easy to throw on and go with practically anything.


One of the simplest ways to guide your wardrobe through the seasons is to let accessories take the lead. Take a beautiful silk scarf, for example — rather than just draping it around your neck, the opportunities are endless depending on how you tie and fold! Wear it tied around your head as a bandana or headscarf, around your neck as a choker, or wrapped around a wrist or bag strap as a chic accent to your outfit. If you’re feeling really adventurous, transforming a scarf into a bandeau top has been all the rage this year and truly show how to carry a single piece from summer into the colder months.

A good pair of boots is another option that will be wearable year-round. Brown leather boots, like these structured chocolate riding boots by Fratelli Rossetti, will pair with skinny jeans and trench coats and easily stomp through puddles when necessary, while these floral detailed boots from Miu Miu can also be worn with tea dresses for a pretty seventies look.

So, that’s it — a basic introduction to transitional dressing for the annoying weeks in-between seasons. It’s all about versatility, choosing pieces that will work in a variety of settings, and those all-important extra layers you can throw on top when it gets chilly that only elevate the outfit further.