Great casual boots needn’t cost hundreds of dollars. If the boots fit well, look great, and are kind to your feet — wear them. With that in mind here’s a selection of casual boots that won’t break the bank. Be sure to look at all the size and colour options. 

• Trotters Blizzard Boot: This Chanel-esque and comfortable weatherproof boot comes in wide widths and goes up to a size 12. Here’s the shorter version if this style is too tall. 
• Sole Society Delma Wedge Bootie: A dressy desert bootie in earth tones. Great in casual settings with jeans, stretchy pants and sweater dresses. Read the rave reviews. 
• Sperry Top Sider Falcon Rain Boot: A rare brown boot for slush and rain.
• Naughty Monkey Chaotic Boot: A quick and stylish pull-on-and-go over skinnies and jeggings. 
• Sole Society Aileen Boot: A vegan moto boot that works well with flirty dresses and slim-fit pants.
• BP. Trolley Leather Ankle Boot: A streamlined casual bootie that goes up to size 13. Read the rave reviews. 
• Dolce Vita Krynn Bootie: Casually perforated, super soft and streamlined at the ankle. 
• MIA Odette Bootie: A slouchy and rugged combat boot that runs half a size large, so size down. 

Remember that suede and leather can be insulated with weatherproofing spray, and that adding cushioning insoles can make a pair of boots a lot more comfortable. I add $2 drugstore bought insoles to all my boots and booties. A couple of dollars that are very well spent.

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?

I went shopping with a long legged, curvy hourglass client last week and she was especially thrilled when we put together this outfit from Banana Republic for casual days at work: tailored striped tee, trouser jeans, and knitted moto jacket. She loves to wear bootcuts, create a tailored silhouette, and feel extra comfortable at the office. She also realized how great she looked in ink blue because it’s a softer alternative to black. 

• Mini-Stripe Timeless Tee: Tailored but not clingy, which is rare to find in T-shirts these days. The low boat neck is flattering on a larger bust and there is a good amount of length. 
• Quilted Knit Moto Jacket: This item has made my top picks lists before. It’s super cozy, streamlined, and can be layered under a coat. Looks fab zipped or unzipped. 
• Indigo Denim Trouser Jeans: Plenty of length, even in regular sizes. Stretchy, but not too stretchy. Great fit over the thigh, tummy, and waist area. I found these too high rise for my own tastes, only because I prefer low rise jeans and trousers. But they are fabulous if you enjoy a girdling fit. 

We finished off the look with black patent tote, low-heeled black booties, and deep red coat. Sizes do come back into stock, so keep rechecking online. Also there was still plenty of stock of these items in brick and mortar stores. 

Some women don’t like to wear three quarter sleeved tops and toppers in Winter, whereas others are happy sporting “cropped sleeves” all year round. Of course, living in mild Winter climates like Southern California, Florida and Texas makes wearing cropped sleeves easy, but I’m talking about wearing this sleeve length in colder climates. 

None of my Seattle clients object to wearing three quarter sleeve knitwear in Winter as long as the pieces are warm, and woolly, and can be worn under a jacket or coat. Some of my clients layer long sleeved T-shirts, turtlenecks, shirts and blouses under cropped sleeve knitwear for forearm coverage. 

Some of my clients wear flimsy three quarter sleeve tops in Winter, especially when they run warm and spend all day in a heated environment. Some will wear them under long-sleeved blazers and jackets, and pop a coat over the lot when heading outside to brave the elements.  

Outerwear is a different story. There is often resistance to three quarter sleeve outerwear styles for practical reasons. You generally want arm coverage when it’s cold enough to wear a wool coat, so baring forearms makes little sense. That said, I do have clients who run very warm and welcome a breezy three quarter sleeve coat. I also have a client who likes to wear opera length gloves with her cropped sleeve wool coat. And I have clients who enjoy wearing lightweight three quarter sleeve coats, cropped and longer lengths, indoors at the office. 

Despite feeling cold at the drop of a hat, I wear cozy and warm three quarter sleeve cashmere and merino wool pullovers in Winter. I layer a camisole underneath and generally feel warm enough indoors. I add a blazer, jacket and/or coat layer when I’m heading outside. I often scrunch the sleeves of long sleeved pullovers, so I’m creating a three quarter sleeve effect with full length sleeves anyway.

I don’t wear blouses and shirts with three quarter length sleeves in Winter. That’s a Summer look for my style. I also don’t wear three quarter sleeved outerwear in Winter. I love the idea of opera length gloves, but haven’t tried that look because I worry I’ll be too cold. I do have three quarter sleeve wool coats that I wear in late Spring when it’s much warmer. 

Over to you. Do you wear three quarter sleeved tops and toppers in Winter?