Outfit Formula: Plaid Skirts and Riding Boots

We see plaid skirts in a variety of lengths every season. One way to make them more wearable in cool weather is to pair them with insulating footwear like booties, dressy knee-high boots, western boots, or stompy mid-calf ‘90s boots. Since equestrian boots are having a fashion moment, the idea is to pair flat black or brown riding boots with solid and patterned skirts too. 

Plaid (tartan or check) skirts in heavier fabrics have an autumnal and wintery vibe. If you have a pair of tall riding boots and a plaid skirt – try wearing them together. Onto some outfit inspiration:

1. Greys, White and Black

A grey and black flared and handkerchief hem plaid skirt is combined with a tight white tee and grey pullover. You can see the white tee peak out from underneath the pullover to create layering interest. A slouchy black bag matches black riding boots and the model’s hair. A slouchy grey beanie works with the palette. A silver pendant necklace adds some shine.

Greys, White and Black

2. Berries, Browns and Cream

A soft and flowing cream and brown plaid skirt is paired with a taupe turtleneck, which picks up one of the browns in the plaid. A guave pink barn jacket with burgundy trim is thrown over the top. It’s mismatched, yet complements the palette. The gingham trim on the sleeves adds a pattern mixed touch. Chocolate riding boots match the brown in the skirt. Add a bag in a shade of brown or burgundy.

Berries, Browns and Cream

3. Sage, Black, Red and Cream

A sage, black, red and cream sequin plaid skirt is combined with a cream welted polo sweater. Its bejeweled buttons add bling to the look. Black riding boots match the model’s hair and the black in the plaid. Add a bag that works with the palette.

Sage, Black, Red and Cream

4. Navy, Grey, Black and Red

A navy, red, gold and white tiered plaid skirt with asymmetrical hem is combined with a cropped charcoal pullover. Black stompy lug sole boots are the shoes of choice instead of tall black riding boots. Visible pearl grey socks peek out from the top og the boots, which match the beanie. A big bag works with the boots. Add jewellery, eyewear, topper, watch and eyewear as desired.

Navy, Grey, Black and Red

Of course, feel free to wear tall riding boots with plaid dresses too.

Fab Finds: Brogue Boots and Hosiery

This week’s fab finds are very specific, and you can wear them together if you fancy the idea. Wearing casual boots with dressy tights creates juxtaposition, or outfit tension. Juxtaposition has become a key styling strategy of our current fashion era. That, and relaxation of dress codes. 

1. ECCO Olso Wingtip Boots

This has been a comfortable and easy to-pull-on-and-off casual boot for everyday wear for clients who have smaller bunions and/or wider feet. The boots come with two footbeds. The thinner one for wider feet, and the fatter one for narrower feet. You can remove the footbeds entirely and put in your own orthotics too. The brogue detailing is particularly on trend. The black soles on the ruby pair make the colour familiar to wear when you’re used to wearing black footwear but feel like a variation. Equally great bookending with black hair, and works well with a black belt. Their high shafts make them great to style with cropped pants. Their streamlined silhouette makes them easy to style with skirts, dresses, and shorts too.

2. Patterned Hosiery

Patterned hosiery can be festive, texture-rich, and insulating to add to skirt, dress and shorts outfits in colder weather. These days, black is not your only option. There are berry tones, all sorts of browns, navy, and Winter whites too. Match the colour of hosiery to shoes, and feel free to mismatch them. Some styles have reinforced toes, making them a more robust option to wear with sneakers and boots. I usually wear nude-for-me hosiery with my dresses and skirts in the colder months, although I fancy a patterned cream pair and might try those to change things up.

Outfit Formula: Plaid Coat

For those who enjoy wearing plaids and would wear the pattern in outerwear, this post is for you. Plaids (or checks and tartans) come in all sorts. The colours of the plaid can be bold, muted, neutral, non-neutral, two-toned or multi-coloured. The scale of the pattern can be larger or smaller. The length of the coat can be shorter or longer. The longer the length, bigger the plaid, and brighter the colours, the bolder the coat. Conversely, some plaids are as subtle as false plains, and almost look solid.

The collection below shows examples of plaid coats.

A plaid coat seems limiting because it’s patterned instead of solid. Although these days, the idea is to just wear it over anything. That might be harder to do in practice because of clashing colours and patterns. Rest assured that if the plaid is in your neutrals, or its colours are well represented in your wardrobe, it will seamlessly work with many outfits. Feel free to pattern mix with a plaid coat too.

Onto some plaid coat outfit inspiration.

1. Statement Plaid Squared

A maxi coat in a navy and toffee plaid is worn over a plaid co-ord in a mismatched plaid. The blouse and trousers co-ord are in a matching green, navy and toffee plaid. The toffee and navy in each of the plaids unites them so that they work together. Bordeaux loafers add a touch of red. A cherry red bag adds more red. A chocolate brown hat adds a trendy touch.

Statement Plaid Squared

2. Sporty Luxe

A pair of very dark blue, dressy flared jeans is combined with a white tee. A black zip-through sweater hoodie is the next layer. A coat in a grey, black, white and red plaid tops the lot. The hood is worn outside the coat for a great visual effect. White sneakers match the tee. A dressy black bag matches the hoodie.

Sporty Luxe

3. Subtle Plaid Squared

An olive, cream and black bias cut flared skirt is combined with an olive V-neck pullover. A black belt is added for waist definition. An olive and black plaid coat tops the lot. The mismatched plaids live in harmony because they share black and olive components. Tall black boots match the belt and the black in the plaids. Plaid coats can work equally well over dresses.

Subtle Plaid Squared

4. Berries Jubilee

Last, black flared jeans are combined with a tucked ombre sweater in black, cream, and cranberry. A back western belt and chunky heeled black boots discreetly match the pants. A conversational berry-toned plaid coat tops the lot. Add jewellery, watch, bag, headgear and eyewear as desired.

Berries Jubilee

It’s been years since I had a plaid coat. I have plaid jackets but no plaid coat. I like bold and subtle plaids. I find them energizing and quite versatile. If the right plaid coat found me, I’d snap it up. How about you?

Roundups

Simpler Items

This week's list of top picks list is about basic pieces.

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Assorted Items

Items for Summer, both in and out of air conditioning.

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Casual Summer Vibes

This week's top picks are good for a casual Summer vibe.

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Summery Earth Tones

These items are for those who like to wear casual earth tones in warm and hot weather.

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Hints of Spring

Some tried-and-tested winning items to refresh your style for Spring.

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Dressier Items

An assortment of dressier top picks might be just what the doctor ordered.

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Fab Find: Dansko Delphine Boots

These waterproof Dansko boots are on sale and have worked for my clients who have fussy feet. They are comfortable, versatile, and quite supportive. You can remove the footbeds to insert orthotics, or add a cushioning insole for extra comfort. They work well for higher arches, but might be snug for high insteps. The heel is less than two inches, and the leather is soft.

They come in two colours. The dark brown version you see below is an inaccurate reflection of the colour. They look more like the taupe you see in the other pictures. The boots can work well with midaxi skirts and dresses, shorts, cropped pants or jeans, and full length pants and jeans. A reliable causally classic style.

Team Metallic or Team Animal Print Footwear

The last poll for 2025 is about a YLF favourite, SHOES. Metallic and animal prints are iconic classics that are having an on-trend moment. That’s why we’re seeing an abundance of the patterns in footwear at retail. Of course if either look is your thing and signature to your style, ignore the trends and wear them for as long as they make your heart and feet happy.

For this poll, any type of metallic footwear counts. Think gold, silver, pewter, or bronze in any style of shoe. Any type of animal print footwear counts. Think snakeskin, leopard, cheetah, tiger, cow, pony, croc, zebra and giraffe patterns across any style of shoe.

I am moody about animal skin prints. I wear them occasionally, so they aren’t a constant in my style. I don’t have animal print footwear at the moment, and haven’t had a pair for a while. On the other hand, I am always in the mood to wear gold shoes. I’ve been wearing gold shoes forever and hope to do so forever more. They hold a permanent place in my wardrobe, and work particularly well to bookend my honey blonde hair. Gold is my metal and I don’t mix metals. Gold shoes are a handy neutral for my style. Weather permitting, gold flats and loafers are “everyday easy shoe choices ” for me. I bat for Team Metallic.

Currently, these are the gold shoes in my wardrobe.

I’m curious to see the outcome of this poll. Do you bat for Team Metallic or Team Animal Print Footwear? Tell us why, and no batting for both teams. If you can’t pick a side, or wear neither, you’re on Team Bench. I’m serving a creamy and comforting leak, fennel and chicken stroganoff over cauliflower and jasmine rice. Baked artichoke and spinach dip for appetizers, and chocolate mousse for dessert.