The combination of wearing full-length flared trousers and jeans with heeled boots might take you back a decade or four. By flared jeans and trousers, I mean silhouettes that are bootcut, bell-bottom, or wide leg. The all important details of the combination are:

• Hems that skim or almost skim the surface of the ground
• Heeled footwear, even if the heels are a low one and a quarter inch
• The refinement and dressiness of the boots

Although it’s not a must, pointy-toe and snip-toe boots work particularly well because their long toe boxes effectively peek out from under the hems, thereby elongating the leg line. Heels further elongate the leg line and allow the breakline of the hems to fall in a tidier drape instead of a crumpled mess. Footwear can create a low or high contrast with the trousers and jeans.

Here are some visuals:

Over the last ten years, we’ve seen every iteration of skinny and tapered bottoms at ankle (and shorter) cropped lengths make a trendy statement with flat and heeled footwear, while this combination of full-length flares with heels took a backseat. More recently full-length flared pants and jeans made a comeback but at a new and shorter full length. The new shorter length is a lot more practical, weather-friendly, looks equally good with flats, and is maybe a dash more playful. But it’s not as elongating, elegant, conventionally flattering, and dressy.

The sleek, streamlined and vertical integrity of full-length flares worn with refined heeled boots continues to be a hit with many people so it never went away. It was especially popular from 2000 to 2012. Some of my clients swear that the combination makes them walk taller, and with better posture. Unfortunately, the need for dry weather can put a damper on the vibe because soggy hems are awful, and heeled footwear is not for everyone. But a sunny climate and commuting by car helps, and low-heeled footwear works well.

Today, I think of full-length flares worn with heeled boots as a Trendy Classic combination that is always sensational, especially when the wearer feels like a million bucks sporting it. When a person’s ease and confidence comes through in an outfit combination, nothing can beat it. So if this was, or is, your look, milk it.

A more size-inclusive line from Jason Wu, strong reactions to a coat shown on a TV show, and more news from the fashion trenches in November.

• Jason Wu is bringing out a more size-inclusive line – with sizes from 0-32 — in collaboration with QVC.
• People are reacting very strongly to the green coat that Nicole Kidman is wearing on TV show “The Undoing”.
• Former Zappos CEO Tony Hsieh has died at age 46.
• Prince Charles and Net-a-Porter have launched a sustainable fashion collection to support textile students in the UK and Italy.
• Stores in China are facing backlash over inappropriate label for large clothing sizes.
• Slovenian inventor Peter Florjancic, who created the compact perfume spray that is still in use today, has passed away at age 101.
• Thanks to the current season of TV series “The Crown” about the British royals, “Sloane Ranger style”, aka the “Diana look” is back.

Fashion Quote

I really liked what Allison Rhone said about her relationship to beauty in her My Beauty Uniform interview on Cup of Jo:

“As I approach my 40s, I feel the best I have in my life. It makes me think of how much time I spent hating what I looked like. For years, I felt too Black, too big, that my features weren’t right, that I just wasn’t inherently right. The last few years for me have really been about acceptance. I find the more I shave off societal ideals, the more beautiful I feel. Being in digital media is such a joy because there are places to go that are not society’s mainstream idea of beauty. I’ll get more from a Twitter thread of Black women showing what they look like, more than a popular magazine. It’s a radical act for a Black woman to love herself. I try to be radical every day now.”

These looks are for those of us who like to showcase a bit of fun sock in their cold-weather casual pants and jeans outfits. Visible socks can add warmth, a maximal touch, textural interest, and comfort. They often make a look more casual. But in some cases, a sheer trouser sock that resembles hosiery can make an outfit dressier. 

1. Lightly Gauzy

Sheer gauzy socks with self-colour patterns that look like hosiery can add a polished and interesting touch to an outfit. These types of socks usually come in black, which is problematic when you don’t wear a lot of black. But they’re coming through in white and occasionally other colours, so keep your eyes peeled.

Here, sheer white gauzy socks are worn with white oxfords for a tonal effect. They match the white pullover and create a lovely low contrast with the pale pink casual corduroy pants. A micro-checked jacket in the same palette tops things off. Alternatively, switch all the white to black, and add a darker pair of pants if that’s more your thing.

2. Maximally Matched

This outfit is neutral and maximal. It’s all about creating a perfect match between a patterned item of knitwear and pair of socks. If you knit, create your own set in any colour and pattern. Throw in a layering top if it’s a cardigan, a pair of bottoms, and footwear that showcases the socks like loafers or oxfords.

3. Birkenstock Pretty

Here’s a cosy, soft and sparkly take on wearing socks with Birkenstocks. Pair a pretty tee or sweatshirt with a pair of distressed cropped jeans. Finish things off with sparkly socks and Arizona Birkensock sandals. The light-coloured Birkenstocks work well with the pink palette, but you can choose a darker palette. Like a black, navy or grey top with sparkly grey socks and black Birkenstocks.

4. Tonally Cosy

Create a tonal effect from top to toe with shades of a similar colour. This version is blue and grey but choose any colour. A greyish oatmeal pullover is combined with a flecked blue-grey coat that picks up the light neutral of the pullover. Fair Isle socks in the same palette pick up the colours of the pullover, coat, and jeans. Importantly, the roomier jeans are rolled to showcase the socks. Grey boots and a navy bag complement the palette. Add jewellery, watch, eyewear and headgear as desired.

Black Friday discounts are abundant as retailers try to clear stock and get a start on the holiday gift-giving season. There is lot on sale, so if bargain shopping is your thing, be sure to take a peek. I’ve seen some of these items in person, some just caught my eye, and others have been winners on my clients or forum members. Be sure to browse the size and colour options.

• SOREL Lennox Lace-Up Bootie: Very comfortable weatherproof boots with arch support. Might need to size up. Swish and different in the white.
• J.Crew Leopard Print Chino Crop Flare Pants: Cropped flares that can work on a curvier body type. Room on the thighs and hips.
• Gallery Long Quilted Parka with Faux Fur Trim: Chic Long Puffer Fabness. The diagonal stitching is visually slimming and the length is GREAT for skirts and dresses. Removable hood. Comes in black.
• Pendleton Park City Water Repellent Down Puffer Coat: Fab water-repellent Winter Woodsy coat for Team Earth Tones. Runs big.
• SCOTCH & SODA Marbled Jacquard Sweater: A casually glam sparkle sweater in a swirly brown animal print is rather unique. Refined and lovely quality.
• ELOQUII Slit Hem Jeans: These work well in mild weather because the slits are very breezy. Works well on an hourglass and apple-shaped body type.
• CLOUD Khia Bootie: A brown tailored shootie in a subtle animal print for Team Brown. Nice neat fit around the lower ankle. Might run a little small.
• Cole Haan Check Coat: A fun coat with an oversized collar for Team Checks. Lovely quality. The large collar works well on square shoulders. The single-breasted style is great on a larger bust.
• Cole Haan Faux Fur Trim Wool Blend Coat: A casually glam coat in a unique shade of antique pink that looks as good unbelted, as it does belted. I don't think the collar is removable but the belt is.
• Alice + Olivia Elaina Tie Neck Paisley Blouse: A bit of pretty and refined '70s Fabness. Best worn without layers, unless it's a coat for outdoors.
• Bernardo Quilted Hood Water Resistant Parka: Streamlined and classic parka fabness. Great colour for Team Green.
• Karen Kane Taylor Long Sleeve Tie Neck Dress: This frock is available in a burgundy and bronze metallic and can work well on petites with a broad shoulder line.
• Kendra Scott Deanna Fringe Earrings: Glam it up at home with these darlings.
• Veronica Beard Ashlynn Floral Polka Dot Stretch Silk Blouse: A pretty blouse for Team Long Neck and Arms. Gorgeous stretch silk.
• Madewell Sidewalk High Top Sneaker: White hi-tops with an earthy rubber sole look fresh. These are canvas and comfortable. Run big and quite wide.
• Lucky Brand Tie Dye Cotton Sweatshirt: Earthy tie-dye looks fresh against a cream backdrop. Cosy up in this sweatshirt, which will take you most places these days.
• Bernardo Knee High Boot: If you have narrow calves and longer legs, and are looking for a dressy tall heeled boot, try these.
• Madewell Dispatch Jacket: A classic utility jacket in a lovely shade of toffee with a streamlined fit. Lots of good reviews, and runs roomy.
• Leith Tiger Stripe Midi Skirt: A tiger patterned tube skirt is unique, and this one is more tailored than body-con.
• Via Spiga Three-Quarter Packable Puffer Jacket: Aqua Puffer Coat Fabness.
• BLANKNYC Meant to Be Moto Jacket with Removable Hood: A faux leather moto that runs small, but has a nice fit. Good on petites. Comes in black with rose gold hardware.
• Rebecca Minkoff Chain Hobo Bag: A classic tote that looks as glam as it does casual. Comes in other neutrals.
• Blondo Cayla Waterproof Chelsea Boot: Waterproof Burgundy Patent '90s Bootie Fabness. Runs a little short in the toe box.
• Blondo Camila Waterproof Bootie: Weatherproof, well-made, and feels very substantial on the foot. Wider feet might need to size up half a size.
• Sanctuary Skip Pump: A fun pump for lower volume feet. Not for fussy feet. Comes in black with a wooden heel.
• Longchamp 'Medium Le Pliage Neo' Nylon Top Handle Tote: A classic Longchamp tote with a handy and comfortable nylon crossbody strap. Comes in colours.
• Rebecca Minkoff Julian Nylon Backpack: If you like this repeat Rebecca Minkoff backpack style and enjoy black and grey, this one is in a '90s nylon.
• Pedro Garcia Lacey Footbed Sandal: A well-made sandal for a higher volume foot in double animal print for Team Brown.
• Tumi Devoe Sterling Backpack: One of the best luxuriously casual backpacks I've seen. Beautifully made and chic. Click the link to get a visual of the fabulous compartments.
• Dolce Vita Bel Bootie: Quite comfortable if you can manage the pointy toe and heel height. Neat ankle fit. Visually crisp and modern.

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