Full-Length Flares and Heeled Boot Fabness

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.

Fashion News Roundup: November 2020

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.

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.”

Outfit Formula: Casual Sock Style

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.

Shopbop
Wolford Dylan Socks
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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.

Nuuly Nellie Corduroy Culottes

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.

Kule Houndstooth Sock

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.

Anthropologie Ines Shimmer Crew Socks

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.

Seasalt Trenwheal Coat

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.

Read More

Hints of Spring

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

Read More

Dressier Items

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

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Nordstrom Black Friday Top Picks

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.

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

Nordstrom
CLOUD Khia Bootie
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Team Pointy, Round or Square

This week’s poll is about footwear toe boxes, and whether you prefer pointy, round, or square toe boxes. All square toes count, including snip toes, round square toes, or very square toes. Almond toes can be pointy or round, depending on the shape. 

I like and wear all the toe box shapes, as long as the shoes are refined. My dressier shoes are pointy-toe with some snip toe and round square toe in the mix. My extensive collection of non-athletic sneakers are round toe and almond toe. But as an ‘80s gal with pointy feet, my heart is with the pointy-toe. They are a natural fit for my narrow feet and long toes, and look good with my dressy style. It was close though. These days I wear round and almond toe sneakers all the time.

I bat for Team Pointy-Toe. How about you? It’s tradition every Thanksgiving that you can bat for more than one team in the poll. No one is benched, and everyone can play. I would love to hear your preferences.

We will be slowing down blog posts this week as the US celebrates Thanksgiving. If you live in the US, we wish you a safe and peaceful holiday weekend.