Wearing skinnies and jeggings tucked into tall boots is an extremely practical combination for the dead of Winter because it’s warm and weatherproof. We end up wearing this uniform, season after Winter season, sometimes for weeks on end. So we’re bored and we need ways to shake things up. Here are six ways to do that. 

Chunky Knitwear

Although the tailored equestrian look with fitted top and blazer is a classic and always in style (check out this gorgeous street style shot of strict equestrian perfection), think further than that combination. Knitwear has exploded this year, and there are lots of new and interesting options to wear on top. By adding these on trend pieces to existing skinnies and tall boots, you’ll refresh the look.

You’re after fluid and oversized silhouettes with high-low hemlines in semi-chunky and chunky knits that make a statement on their own. Think mixed media and a little or very slouchy. 

The picture above is one inspiration, but by all means wear pullovers longer if you prefer to cover up part of the hip and bottom. Remember that roomy tops visually narrow the hips and thighs, creating an inverted triangle silhouette just like they did in the ’80s. No topper required other than a coat for when you head out to brave the elements. For more visuals refer back to yesterday’s sweater post, and check out this chic street style example with hectically oversized poncho. 

On Trend Outerwear

Matching skinnies and tall boots with on trend outerwear instantly refreshes the uniform. Think cocoon coats, round-shouldered styles, capes, maxi coats, and man coats. Look at how stylish this lady is in her Winter cape. 

Wearing a trapeze-poncho silhouette like the one below is another way to go. No need to wear bold patterns if that’s not your thing. Stick to solids and create a low colour contrast between all the pieces in your outfit for a more streamlined effect. 

Patterned and Colourful Bottoms

Sleek black ponte pants and blue skinnies are NOT your only options when it comes to bottoms. Think cobalt and burgundy skinnies, and patterned skinnies like tartan, camouflage, geometric designs and florals across a variety of fabrications. There is metallic denim for Team Magpie, and flocked and waxed denim for Team Texture. Moto jeans, leather jeggings, and white jeans are another way to go.

Recently I’ve been tucking last year’s gold jeans into tall black boots and finishing off the look with a fluid untucked black turtleneck, just to change things up.

Baggier Bottom Fits  

Wear bottoms that are looser than skinnies, like streamlined boyfriend jeans or slouchy skinnies. This combination is an acquired taste because it creates poufing, bagging and creases on the leg line. Skinnies are sleek and look like a second skin when tucked into boots creating a polished effect, whereas baggier bottoms create a more RATE (rough around the edges) vibe. 

My boyfriend jeans are too baggy to tuck into tall boots, so I’ve been going the slouchy skinnies route. You may remember this outfit from last year when I paired stripes with checks and an ink military coat. The skinnies are baggier all over creating an extra relaxed vibe. 

Try tucking slouchy, harem trousers into tall boots if the bottoms are adequately tapered. The vibe is much like wearing breeches with boots, as demonstrated by this lovely lady. By all means try a less slouchy version too. I like to tuck my jodhpur jeans into tall boots to create a similar silhouette without the dropped crotchpoint. 

Mid-Calf Boots

Wearing shorter mid-calf boots is the fifth way to refresh the uniform. The two pictures below showcase casual mid-calf boots, which is one way to achieve the vibe. Create a low contrast between the colour of the boots and bottoms if you’re concerned about the leg shortening and “stump factor” of shorter boots. Wear heeled versions for an even longer leg line. 

I plan to embellish these ideas in ensemble posts over the next few weeks so that we can break down the components even further. Do you tuck skinnies into tall boots? Have you felt a need to refresh this outfit combination because it has begun to feel stale?