Outfit Formula: Skirts and Stompy Boots

If you enjoy wearing rugged flat chunky boots, combat boots, or classic riding boots with skirts — as some of us did back in the ’90s — these looks are for you. The boots can be any height, with zipper or laces, and have lugged soles. They can be any colour and pattern, but solid black stompy boots are the most popular. Black boots also work well when you have black hair and/or wear a lot of black in general.

These outfits range from dressy to causal, and are neutral and earth-toned. Feel free to create similar looks in your own palettes. In most cases the dressy skirts create a jarring juxtaposition with the casual boots, which is the appeal of the combination.

1. Dressy Bomber

In this creative combination a dressy skirt is combined with a very casual graphic tee, which is semi-tucked to hint at a waistline. Tall, flat and black casual riding boots pick up the black in the tee. The sporty bomber is another interesting piece because it’s a casual item made of dressy fabric. The gold matches the skirt and the black cuffs match the tee and boots. The short length of the jacket lengthens the leg line. Beautiful!

Dressy Bomber

2. Columned Layers

This is an extra comfy combination because it combines three very fluid layers. A flared skirt is paired with a loose blouse in the same colour. A jacket in the same neutral is popped over the top to create an elongating column. Black riding boots and toffee cap finish off the look. I’d have preferred to see brown boots to soften the contrast, but the black boots make a dramatic statement. Why not!

Columned Layers

3. Ruffled and Sleeveless

This type of look makes sense in a warm Fall or Winter, when you don’t necessarily need a topper, and you can go sleeveless if you want to. I particularly like the contrast between the ruffled skirt and combat boots. The fluid sleeveless top is an elegant addition, and the semi-tuck hints at a waistline which adds some structure. You can create a low contrast with a darker top if that’s more your cup of tea. Or wear cream stompy boots to match the top.

Ruffled and Sleeveless

3. Sweater Vest and Pencil

Here’s a version with a pencil skirt or tube skirt. Combine it with a shirt, blouse, or tee and layer a sweater vest over the top that matches the top and skirt. Add a pair of stompy boots, a bag to match, and Bob’s your uncle. Here, the black boots match the black in the pattern of the skirt and the bag, thereby pulling things together. They also bookend the model’s hair. Add jewellery, watch and eyewear as desired.

Sweater Vest and Pencil

A Collection of Fun Skirts

Skirts are in great supply this season, and here is a collection of fun, fab examples. Some of them have worked well on clients and forum members, and others have good reviews online. 

It’s great to see skirts styled with a few more UNTUCKED tops at retail these days, because in my experience, that is how most people like to wear them. Many of these skirts come in multiple colours, so be sure to browse the items on their respective websites.

Abingdon Mini Skirt
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Long Satin Skirt
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Leather Midi Skirt
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Leather Midi Skirt
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BROGGER Sigrid Skirt
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Rachael Skirt
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Spotlight: Harper Wilde

Jane and JennaBra company Harper Wilde manufactures bras and panties sustainably, ethically, inclusively, and a lot more affordably than you would expect. Founders Jane Fisher and Jenna Kenner are committed to creating comfortable, high-quality bras that are offered at fair prices. You can read more about the brand’s compelling mission and story, as well as how they lift the leading ladies of tomorrow.

Items are well worth a browse if you’re shopping for simple bras and panties with a more utilitarian vibe. You can buy bra and panty bundles, and get help with the right sizes and styles. The smallest band size is 32, and the largest bralette size is 3XL. The brand is not as size-inclusive as I had hoped, but it’s a good start.

Bra Colors

Harper Wilde’s bra recycling programme is forward-thinking. Bras usually consist of at least thirty pieces, making them very tricky to dispose of sustainably. Most end up in landfills because it’s the easiest thing to do. So Harper Wilde developed a process that helps you recycle your bras more sustainably. Impressively, they accept ANY brand of bra (and underwear).

Click the “RECYCLE BRA” button on the site to start the process. Follow the steps, and you’ll help save the planet. Harper Wilde will send a recycling kit to send back your old bras and panties. Once they’ve received them at their recycling centre, they break them down. Some parts are upcycled into yarns and fabrics, while others are broken down and used for things like rugs, cleaning textiles, and building insulation. They will cover the costs of recycling your bras, but you pay the price of shipping your bras to them. If you choose to place an order with Harper Wilde, you’ll receive a pre-paid label which covers the cost to ship as well.

I love hearing about companies that are run by women who are doing good things for other women and the world. Harper Wilde does not currently make my bra size, but that might change. I also tend to prefer my undies with a bit of lace, but I can certainly recycle my bras with the brand.


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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Weekly Roundup: Hints of Fall

Most people I know enjoy dressing for Fall. I bat for Team Spring and Summer, but Autumn is magical in its own way. I enjoy the change of dress from Summer clothing, as well as the glorious fiery foliage. Onward to a stylish and fabulous Fall. 

Stock levels are low at most retailers, especially in brick-and-mortar stores. I suspect this has a lot to do with ongoing supply chain issues brought on by the global pandemic. That said, retail looks better than it did last year. I had a good browse at our Scotch & Soda last week and the items are incredible if you like earth tones and a sense of practical sporty chic with an edge. Beautifully made as always. Very proud of this Dutch label that continues to be fabulous. Browse the colour and size options.

  • SCOTCH & SODA Short tweed jacket: The cut of this short tweed jacket is AMAZING. The sleeves are works of art, and like origami. It is particularly good with skirts, dresses and high-rise bottoms. It glides over your figure like a jigsaw puzzle that fits. It would be mine if it weren't earthy.
  • SCOTCH & SODA Crewneck Sweater Vest: If you like slouchy vests, high necklines and coppery cinnamon - try this one. The high neckline and welt give it ample structure.
  • SCOTCH & SODA Houndstooth Check Blazer: An on-trend '90s inspired blazer that is more lilac in person, and has cigarette pants to match.
  • SCOTCH & SODA Classic crew neck sweater: Navy and cinnamon stripes are unique, and the fluid fit of this one is yummy. Silky to the touch, and with a retro '80s dropped shoulder.
  • SCOTCH & SODA Reversible printed bomber: Silky reversible bomber jackets are signature to this brand, and these are beautifully luxe. Click the link to see four pattern options.
  • SCOTCH & SODA Knotted relaxed-fit sweater: The slouch of this pullover is tempered by the front knot detailing, and the varied directions of the rib. It's less bulky on the body than you expect, and comes in oatmeal.
  • SCOTCH & SODA Padded wool-blend shirt jacket: This shacket is quilted for warmth, and graphically divine in the navy and olive windowpane. I like the way it hangs very straight and is beyond body type. STUNNING quality.
  • SCOTCH & SODA Relaxed fit printed shirt: This pattern is beautifully different, and so is the olive version. The blouse feels luxe, is textured, and LONG. Fab for Team Tall.
  • Everlane The Cotton–Merino Floral Crew: A graphic floral that looks as good and pretty in the grey and lilac. The sleeves are GORGEOUS, and are fab under a cape. The welt adds excellent structure. The yellow is more muted in person.
  • Zella Sleek Track Pants: If you like to wear streamlined joggers in a brighter shade of olive, try these. They are thicker than the norm, and run a little big. They mould to the shape of most body types.
  • OluKai Pehuea Li Convertible Sneaker: These are the best crisp and clean low-top earthy sneakers of the year. Comfy, rich, and neat on the foot. Fits a range of foot shapes.
  • Madewell Addition Quilted Packable Puffer Jacket: GORGEOUS quality lightweight puffer that looks more architectural than you expect. At first I thought the length was odd but the slight swing of the silhouette works well with the length. It might be a little roomy if you like a narrow fit. Comes in sage green.
  • KOBI HALPERIN Gianna Jacket: Cobalt jackets have been scarce, making this one all the more fab. Ruffled in an architectural way, and works particularly well on straighter and apple-shaped body types. Comes in black.
  • Liverpool Classic Denim Jacket: Earthy Denim Jacket Fabness. Stretchy, soft, versatile, and comfy.
  • HOBBS LONDON Martie Boxy Denim Jacket: A very clean and crisp olive jacket that is beautifully made. Good with dresses, skirts and pants. Nice fluid fit.
  • HOBBS LONDON Hackness Tailored Blazer: I have two of these from a couple of seasons ago, and they are high-quality versatile pieces for my style. They fit beautifully, and are a wonderful shorter length. I've worn them on long flights, they are that comfy and do not crease. They will be on the narrow side if you prefer a roomier fit. Good on narrow shoulders.
  • KUT from the Kloth Quinn Faux Suede Moto Jacket: Machine Washable Suede Moto Fabness. Might run a little big. Comes in more neutrals.
  • COS Colour-block Fine-knit Top: This is a beauty if you like to remix earth tones with a saturated pink or peach. Fluid, long, and very cosy.
  • CeCe Clip Dot Long Sleeve Blouse: An easy boho-inspired blouse that's fluid but not baggy. Good on a larger bust, and forgiving on the midsection. A Swiss dot is pretty and refined, and this comes in many colours. No need to semi-tuck.
  • Boden Charlotte Cardigan: A unique navy cardigan with a collar and white buttons. It's long so great for Team Tall or Long Torso. A knit with some weight, and a bit like a sweater jacket.
  • SCOTCH & SODA Printed high-neck slim-fit T-shirt: These slim-fit tees come in an assortment of unusual earthy patterns. They are great to layer under toppers, vests, and dresses too.
  • SCOTCH & SODA Cowl Neck Sweatshirt: Fashion sweatshirts are the bomb and give knitwear some competition. Pumpkin spice and all things nice, although there is a cream version. The sleeves make the sweatshirt unique, and the T-neck collar can be folded down.
  • Everlane The Sleeveless Turtleneck: This can be worn as a top and layering item under a topper. Or as a vest over a top or dress. It's fluid and looks elegant.
  • Banana Republic Sweater Hoodie: I got this in the cream to wear under my new sandy windowpane Hugo Boss pants suit with hybrid gold wing top sneakers. or cream boots. The cream is rich, and the fabric feels yummy and substantial. It's mostly made of an eco-friendly viscose, which is a natural fibre. I love the higher neckline of the hood. It also perfectly matches my new cream combat boots so it will get lots of wear.
  • Boden Phillipa Rugby Top: If you enjoy rugby stripes, this one comes in unusual colour combinations.
  • SCOTCH & SODA Printed scarf scrunchie: Try a scrunchie with a scarf if you pop your hair into a low or high ponytail.
  • Whistles Denim Pleated Midi Skirt: An interesting denim skirt with fun front and back basque detailing. That's the part you can showcase by tucking or semi-tucking tops. Fab twirling potential. Looks great with tall flat stompy boots too.
  • Boden Cashmere Sweater Vest: A classic and more fitted vest to wear as a top, or pop over a blouse or shirt. Lots of colours.
  • Cole Haan Women's Zerogrand Wing Oxford Closed Hole Ii: A Cole Haan iconic classic that is half sneaker and half oxford. Very soft, comfy and ligthweight. Comes in more neutrals.
  • Converse Chuck Taylor All Star Berkshire Water Resistant Sneaker Boot: I tried these and almost kept them because they are VERY comfortable, warm, and water resistant. The fleece lining is sublime. The white is more cream in person. I returned them because I want the outer fabric to be leather. Comes in black. Extremely lightweight.
  • Boden Elizabeth Coat: A statement coat in navy velvet paisley. DELICIOUSLY different. It's a versatile length and fit, and I like the back boxy pleat. Dress it up or down.
  • Gap Organic Cotton Joggers: These thick and substantial cotton joggers come in Tall, Petite and Regular lengths across five neutrals. They are partly made of Reribra which is an ecological fabric made of upcycled cotton scraps from pre & post consumer cotton waste. They have a half elastic waist, and the cut moulds to most body types.
  • Banana Republic Leather Hobo Bag: A fab light neutral bag to wear as temperatures drop. Lies flat against the body and anchors well on the shoulder.
  • Miz Mooz Dylan Sandal: These can work really well in a hot and warm Fall and Winter, and come in other neutrals. Soft, buttery, comfy, well-made, and a little rugged.
  • Everlane The Modern Breton Tee: An earth-toned Breton striped tee is a rare find, and this one is great. Lovely quality, and nice slouch. Comes in two more stripes.
  • Talbots Terrier Brooch: I'm not a big brooch and earth tone person, but HAD to have this Yorkie brooch because it looks like our little Jo. A completely emotional purchase, and I am high fiving all Terrier lovers!

You can see the pictures alongside the items on the collection page.

Charlotte Cardigan
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Phillipa Rugby Top
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Cashmere Sweater Vest
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Elizabeth Coat
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Organic Cotton Joggers
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Terrier Brooch
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Your Personal Figure-Flattering Priorities

Style is art, not science. Opinions about it are subjective. What makes an outfit flattering is in the eye of the beholder. Also, there is no one way to be stylish, and an outfit has to feel right in order for you to wear it with joy and confidence. Body type dressing guidelines and traditionally flattering outfit proportions can be helpful as a starting point, but they are by no means essential. Not at all.

Instead, I suggest creating a PERSONAL set of figure-flattering priorities. These are guidelines about fit and outfit proportions that are unique to you. They empower you to dress the way you want to, instead of being boxed into a so-called look that is based on your body type and someone else’s benchmark of beauty. After all, you’re wearing the outfit, so how you perceive it and feel in it is most important.

When I work with my clients, we establish their personal figure-flattering priorities. I listen closely to what types of fits and proportions makes them feel great, and I apply that knowledge to their style. That way their outfit creation process is set up for success, and their style is authentic. When clients are unsure whether a look is flattering or unflattering, I offer my two cents. Often the look in question IS flattering, but they aren’t yet used to the new proportions.

I’ll start the ball rolling by sharing my own set of priorities. They have evolved over time and adapted to my changing needs. I am a stickler for perfect fit, and will go to a lot of effort to create it. I do not need to look my narrowest in an outfit. I will surrender my waist, and wear boxy and baggy items if I like the look. Creating height is also not a priority.

1. Fluid Fits

I do not like to wear clothing items that are too form-fitting and constricting. I’ll define my waist and wear tailored items, but there has to be ample fluidity in the outfit too. I’m energetic and active, and need to move in my outfits (with doggies in tow). So my tailored fits are on the fluid side. Functional flow is key.

2. Oversized Structure

When I wear oversized items, like big and breezy Summer shirts and shirt dresses, I do so with structure. I tuck or semi-tuck the shirts to create a bit of a waistline. I also scrunch the sleeves of the shirts and dresses to reveal forearm skin, because showcasing skin creates structure.

3. Knee-Covering Dress and Skirt Lengths

I do not like showing my knees in skirts and dresses anymore. To my eye the look on me is better when the lengths are midi, midaxi, or just covering the kneecap. There is nothing wrong with my knees, but just because you can wear something, doesn’t mean that you need to. I enjoy the elegance and fun factor of skirt and dress swoosh, so its knee-covering lengths for me.

4. Neck Shortening

I have a very long neck, and my short hair makes my neck look even longer. So I wear high necklines and shirt collars that visually shorten the length of my neck, and stay away from scooped necklines, boat necks, low necklines, and most V-necks. I will also effectively fill the gap of a slightly too wide neckline with a pearl necklace.

5. Strong Shoulder Line

I am small framed and have narrow shoulders, so I like to keep my shoulder line structured by wearing items that are tailored on the shoulders, and by wearing a neckline with ample coverage. I can wear dropped shoulder silhouettes as long as the style has a high neckline, or shirt collar.

6. Long Enough Leg Line

I don’t have a naturally long leg line, and do not feel the need to create one by wearing heeled footwear. But I don’t want to feel overly short in the leg either. So I strive to create a leg line that looks long enough to me. I create one without high heels by semi-tucking or tucking tops into high-rise bottoms that lengthen the leg line from the hips upwards. I wear untucked tops that aren’t too long so the torso is visually shortened. Or I wear long untucked tops with diagonal hemlines.

7. Tailored Boots

I have narrow ankles and calves, which makes most booties and taller boots gape at the opening. Think of a stem in a flower pot as a visual. I do not find this flattering on my body, so I’m extra fussy about how my boots fit. They need to be tailored, streamlined and neat around my ankles and calves. Very little or no gaping is key.

8. Pant Lengths

And last, pant lengths are my thing. I will nitpick about their lengths, and how the type of footwear worn with them and the silhouette of the pants itself is affected by creating just the right length. To my eye, half an inch shorter or longer can often make a visually important difference.

Over to you. Care to share your personal set of figure-flattering priorities?