Outfit Formula: Off-Kilter Skirt Looks

It’s more of a skirt season than I expected. Go Team Skirt! Lengths from micro mini to maxi, and every length in between are on-trend. There are countless ways to style skirts these days as wearers prioritize comfort, work with what they have in their wardrobes, stay warm in Winter, and do their own thing. The results are creative and interesting. 

Here’s a smattering of off-kilter skirt outfits. Combinations are unexpected, playful, interesting, and in many ways quite practical. Some looks are more structured than others.

Juxtaposing dressy items with casual ones is one of the defining themes of our current fashion era, so you’ll see a lot of that. Statement socks are on-trend so you’ll see a lot of that too. There’s pairing body warmers, puffers, and belted jackets with skirts. Wearing neckties with shirts. Bomber jackets with ball gowns. Cowboy boots with corporate skirts. Oversized layers with pleats, sweatshirts with bling, and plaid tops with sequin skirts. Any type of footwear goes. From heeled pumps, strappy sandals, and dressy tall boots, to booties, stompy boots, riding boots, western boots, flats, loafers, Mary Janes, mules and sneakers.

On to outfits that might inspire your styling techniques. Choose any colour palette.

1. Puffered Sequins

A sequin pencil skirt is paired with a fitted, sheer and tucked mesh turtleneck. A bright, short and fitted cobalt cardigan is buttoned through and worn as a top. Its V-neck allows the mesh top to shine through. Black opaque tights and pumps give the effect of tall dressy boots, and bookend the model’s black hair. The lot is topped with a very short and shiny black puffer jacket. It’s worn open to showcase the blue cardigan.

Puffered Sequins

2. Shirted Sweatshirt

Wearing fashion sweatshirts with all sorts of skirts is a way to dress them down. They can also be more breezy and comfy than a woolly sweater. This look combines two casual pieces with three dressy ones. The sweatshirt and sporty skirt are very casual. The button-through shirt, structured bag, and mules are dressy. I like how the white shirt picks up the white slogan on the sweatshirt, and adds a crisp and strict touch. I’d have left the sweatshirt untucked for a relaxed vibe. The black complement of shoes and bag works well with the model’s hair.

Feel free to leave off the shirt, and stick to sweatshirt and skirt. Add bling to dress things up.

Shirted Sweatshirt

3. Cosy Satin

A buttery and dressy satin bias-cut skirt is paired with a cosy, long and roomy burgundy pullover. I’d have scrunched the sleeves to create structure because “skin = structure”. That said, when it’s cold, arm coverage is fab. The long sweater gives the silhouette a dropped-waist integrity. Black fishnet hosiery adds a textural touch. Wearing sandals with hosiery is on-trend, although feel free to wear closed shoes. The gold sandals here work well with the buttery tone of the skirt. I see a gold necklace of sorts to finish off the look.

Cosy Satin

4. Maximal

This is genius outfit composition, and as maximal as a festive Christmas tree. It may not be your cup of tea, yet its creativity deserves appreciation. Wild, and to my eye successful pattern, colour, texture, and proportional silhouette mixing. A red and white button-through shirt is worn under a cream Scottie Christmas sweater. Those layers are worn over a billowing blue and green tartan taffeta skirt. Red socks are worn inside black and cream haute hiking boots with red laces to match. The cream vamps of the boots match the cream sweater and pearl earrings. The lot is topped with a short black sequin jacket, and red tartan scarf tied inside the shirt collar. The black in most of the outfit components helps pull the look together. The only thing missing is a terrier under the wearer’s arm.

Maximal

Weekly Roundup: Assorted Items

The ‘90s influence on fashion continues to be strong. Jewel tones are back, and red makes its trendy statement. This week’s roundup includes a bit of everything. Browse the colour and size options, and delight in the fact that some items are on sale. 

  • Lafayette 148 New York Cotton Pleated Midi Skirt: A gorgeous and interesting dressy denim skirt for Team Swoosh. It's well made and on sale. It's more grey than blue in person, and very long. It was almost maxi length on me, and I'm 5ft 6. Zero stretch.
  • J.Crew Long ruffle skirt in Black Watch tartan: A fun skirt with a cheeky ruffle that works on a range of body types because of a fairly forgiving fit. The front slit isn't too long, and can be sewn a little closed too.
  • Ann Taylor Geo Tie Neck Top: Pussy-bow blouses have their late '70s and early '80s appeals and are popular with my clients who enjoy wearing them tucked into skirts or wider pants. They work well worn untucked over slimmer jeans too. Packs a punch under a blazer.
  • Ann Taylor Floral Smocked Mock Neck Popover: Blouse that looks great worn untucked over pants and jeans. The smocked raglan sleeve adds an effective bit of interest and structure.
  • Loft Striped Cat Sweater: Black and white striped kitty pullover that is selling like hot cakes, and comes in petites.
  • Loft Belted Devin Slim Pants in Plaid: These checked cigarette pants have a fab '90s turn-up, and their rayon content gives them a lovely soft and comfy drape. A high stretch content ensures a forgiving fit across a range of body types. Size down.
  • Topshop Tilda Crop Denim Jacket: Zero Stretch Boxy Denim Jacket Fabness. On-trend, not too long, not too stiff, and no need to order a size down. I love the straight architectural fit. It's mine as a replacement for an ancient denim jacket that bit the dust. Comes in black.
  • Stuart Weitzman Sleek 60 Loafer (Women): '90s Dressy Black Heeled Loafer Fabness. Refined, and fits a narrower foot. Good for long toes.
  • Linea Paolo Wink Bootie (Women): '90s Block Heel and Square Toe Fabness. Runs short in the toe, although the toe box is on the roomy side. Quite comfy, neat ankle fit, and comes in black. Wear these with bottoms that showcase the hardware.
  • MONICA VINADER Alta Capture Charm Bracelet: A chunky modern chain link bracelet with a dainty integrity. The links can be removed so the size is adjustable. Wear it as is, or convert it into a charm bracelet. Comes in other metals. Versatile. A piece that can be worn daily, and with your watch.
  • Boden Canterbury Velvet Coat: Patterned Velvet Coat Fabness. Comes in a solid darker green. Quite fitted, and does not hang straight. Lightweight. Impeccable.
  • Boden Margot Velvet Midi Skirt: A straight velvet skirt in an unusual shade of silvery mid-tone green. Comfy with a bit of stretch. Moulds to the body and fits a range of body types. Comes in navy and a pattern.
  • Babaton forever sweater: A good sweater to wear with a flared skirt if you want to showcase a defined waist, and don't mind a higher neckline. Comes in pearl grey.
  • Babaton rennie satin blouse: A lovely teal blouse that's fab under a jacket, vest, or tucked into bottoms. Best on a smaller bust. Might run roomy.
  • Babaton process jean skirt: A pleated denim skirt that looks as classic as it does on-trend. Wear it year round with the right seasonal support act. Comes in a lighter denim. I tried it and hoped it would be longer on me than on the model. It was the same just-over-the-knee length. I passed because I wanted another 10 inches of length. Super cute on someone else.
  • Madewell V-Neck Button-Front Sweater Vest: A gorgeous and well-made sweater waistcoat. The front detailing is stellar if you look up close. It works well on petites and on a shorter torso. Comes in oatmeal.
  • Vionic Women's Charm Lani Lace Up Ankle Boot- Comfort Booties for Heel Pain, Plantar Fasciitis with Built-in Arch Support Orthotic Insole That Corrects Pronation and Alignment, Medium and Wide Width: Supportive, comfortable, soft, and with a sturdy sole. Chunky in a refined way, with a practical side zipper. No need to tie and untie the laces. Comes in many neutrals. The olive patent is unique. Best on a lower volume foot. Plenty of room for long toes. Lightweight. I nabbed the cream for $62.
  • Madewell The Alonzo Coat in Bouclé: Teal Cocoon Coat Fabnes. Textured, long, big, boxy, and great to wear over chunky knitwear, hoodies, sweatshirts, or jackets because it's roomy. Comes in a cool-toned light blue and black.
  • Ted Baker Emallly Branded Jacquard Knit Sweater: I was unexpectedly wowed by this and it followed me home. It's a GORGEOUS casual sweater. The front branding is hard to read in person, and looks more like a random abstract design. It's longer and more fluid on me than on the model, who does not do the item justice. The model needed to size up for a better fit, IMO. Stunning architectural straight drape, and a very neat and tidy neckline. Just how I like it! I'm wearing it with blue and ecru jeans, cream boots, pearls, and a bag in the same shade of tan.
  • J.Crew Brushed woven scarf in stripe: The trendy scarf of the season. Comes in solids, and the fluff does not irritate your eyes and nose. Not too long, and can do double duty as a fab wrap.
  • Ecco Sculpted LX 35 Bootie (Women): Extremely FAB boots with outstanding lower sculptured round heel. Very comfy, sturdy, robust, and chunky in a refined way. Grippy soles. Neat ankle fit. It has two sets of insoles that are removable so you can insert orthotics, or remove one insole to create a roomier fit. Fab for high insteps and arches. Can work with smaller bunions too. Comes in black and black patent.
  • AQUA Cashmere Skull Print Hoodie - 100% Exclusive: Cashmere Skull Hoodie Fabness. Comes in beige and is on sale.
  • Ted Baker London Hanaly High-Low Sweater: This versatile and dressy satin-front sweater was KILLER on my petite client. Works well on a larger bust. Dress it up or down. The welt blousons the top making it work fably with skirts and wide bottoms. Forgiving on the midsection
  • Ted Baker London Raychi Floral Pleated Midi Skirt: A moody floral skirt that works straight into the Dark Romance theme. Fab with a black sweater and shoes. Dress it up or down, wear it for the festive season, and beyond.
  • Nordstrom Macombs Water Resistant Moto Boot (Women): Reasonably comfy, room in the toe box, weatherproof, robust, and on sale for $60. Comes in black.
  • Maje Faux Fur Coat: Very pricey and very fabulous. A spectacular '70s poodle jacket that is SO MUCH FUN. I tried it on and was launched into orbit. Roomy, a forgiving fit, not too long, and very comfy. The fabric did not aggravate my eyes, skin, and nasal passages. It's a lot of collar, so you have to be good with that. Awfully dramatic and impractical. We only live once! Waiting for it to go on sale.
  • J.Crew Classic mariner boatneck T-shirt in stripe: Simple Classic Breton Stripe Fabness. Fab price.
  • Black Halo Coralia Tie Neck Tweed Jumpsuit: A SPECTACULAR dressy occasion jumpsuit that does not crease, and will knock your socks off if you like the fit and silhouette. Substantial fabric. The cape-esque sleeves are fully lined and drape like a dream. Genius design. Best on those who like to define their waist. Pants are easily hemmed shorter. It might feel fussy to wear, but remember this is NOT an every-day item, and you don't needy to run a marathon in it.
  • Rag & Bone Addison Wool Scarf: Versatile scarves that double duty as wraps are hard to find in this deliciously saturated shade of lilac. Luxe, substantial, and with a high longevity-factor. Comes in bubblegum pink.

You can see the items alongside my descriptions on the collection page.

Ann Taylor
Geo Tie Neck Top
View Info
Top Pick
7
Loft
Striped Cat Sweater
View Info
Top Pick
4
Nordstrom
Maje Faux Fur Coat
View Info
Top Pick
6

Exploit the Versatility of Modern Classics

Fashion showcases modern classics decade after decade, for good reason. They are simple, versatile, easy, and can be transformed into almost any style or vibe. Sometimes modern classics enjoy a fashion moment and become trendy for a while. 

Claim the Classics

Banish the idea that modern classics are boring. Refresh them to keep them current. Wear them in non-neutrals for extra punch. Adapt them in fresh ways. Pick them when the trends aren’t for you. Hold onto them, making your wardrobe more sustainable.

Striped sweaters, moto jackets, Dr. Martens, cowboy boots, Birkenstocks, button-down shirts, Wayfarers, tailored blazers, trench coats, sheaths or hoop earrings. Modern classics are comforting, familiar, and take on the personality of the wearer.

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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Playful Patterns in Navy

A new outfit from Sabra Johnson of My Style Is My Brand, whom we introduced to YLF in May 2022.

Leave it to Sabra to create an elegant head-to-toe navy look with loads of visual interest. They’re all slightly different tones of navy blue, and work splendidly together. Our blogger has dressed up wide-legged tuxedo-striped pants with a meticulously tailored blazer and a satin pussy-bow blouse. There’s playful pattern mixing going on with the on-trend pinstripe long blazer and the white and blue polka dot blouse. Tucking the top lengthens the leg line from the hips up, and showcases a thin silver metallic belt. The structured satchel amps up the dressiness, and juxtaposes cleverly with fun, oversized hoop earrings and statement arm candy. Sabra’s blue and white striped pointy-toe pumps peeking out from under the full-length pants are the icing on the cake for me. They add a touch of whimsy and echo the pinstripes, tying everything together.

Sabra Johnson - 2

Sabra Johnson - 1

Team Change or Team Same

You are on Team Change if you like to change up your look. You are on Team Same if you prefer your look to the stay same from day to day, season to season, or year to year.

As I picked a team for this poll, I enjoyed reflecting about how my style has changed daily, seasonally, and yearly. I also thought about my style through the decades. The result is that I can’t pick a side. I like change, but not too much change, and not at all at once. 

Some components of my look have stayed the same for decades. Sour brights, white bottoms, pearls, blue denim, shirts, polo shirts, high necklines, statement bags, blonde hair, classic silhouettes, classic patterns, short jackets, dressy looks, flats, refined footwear, minimal jewellery, and a certain amount of structure — these are all part of my signature style. I enjoy wearing outfits that are pretty, playful, practical, polished, and a little retro. This is reflected in my day-to-day style. My make-up routine has  stayed the same for forty-five years.

Other components of my style have changed daily, seasonally, yearly, and through the decades. Weather permitting, I like to switch up between pants, jeans, dresses, skirts, and the occasional jumpsuit frequently. That way, I don’t feel bored with my style. I wear as many non-neutrals as neutrals, and am perpetually combining colours in new ways. I tend to keep my bottoms and eyewear trendy, so those aspects change the most frequently. I change outfit proportions and fits as I adopt trends that tickle my fancy. My hairstyle goes through big and small changes. I used to wear solid black, but switched to solid navy. I go through stages of wearing more solids than patterns, and vice versa. Some seasons, I’m more in the mood to pattern mix than others.

I like to change up my look, and keep it the same. The changes pander to my need to feel refreshed, current, modern, and energized. The sameness keeps my style grounded. I am benched.

Over to you. Do you bat for Team Change or Team Same? Tell us why, and no batting for both teams. Feel free to join me on the bench where I’m serving Beyond Beef meatballs in sundried tomato sauce, baked broccoli cheese casserole with a cayenne pepper kick, cauliflower mash, and a flourless brownie with chocolate sauce and ice cream.