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Winter Outfit Ideas with Heels

5-minute read

Heels are the ultimate outfit-finisher. Heels add polish to casual weekend looks and elevate office wear. Poppy Barley heels prove that comfort is anything but boring. Our heels are playful with details like square-toes, exaggerated buckles, metallic grommets and sporty pull-tabs. They are designed to be versatile and work for 80% of your life.

We asked fashion stylist Julianne Costigan to show us how to style our heels to transition from fall to winter. Build your outfit from the ground up (heels, first!) with these great tips.

Julianne Costigan Poppy Barley Heels Styling

Meet Julianne

Based in Toronto, Canada, Julianne is a fashion stylist known for her effortless ability to combine the quality and aesthetic of luxury brands with the ease and accessibility of mainstream fashion. Julianne’s sophisticated approach to style is known throughout the industry, as she focuses her work on personal and celebrity styling as well as advertising and editorial projects. The Julianne Costigan team forges trustworthy, female-empowering relationships with risk-taking, rule-breaking, glass-ceiling-shattering clients, bringing their values, stories, skills and goals to life through style.

What are your favourite ways to wear heels in the fall?

Look 1: The Power of Red

Red is a powerful colour, and when applied to a great heel? Magic happens. The Daily Heel in Poppy Red allows you to inject personality, and interest into the simplest of outfits while complementing and enhancing more elaborate looks. For this outfit we paired a bold patterned blouse, charcoal denim and a beige clutch, allowing the red shoe to take centre stage. For a more casual work look, try pairing your red heel with a great high waisted denim, a striped tee or white button up and your favourite classic blazer or leather jacket. Take the look from day to night by swapping out your denim for a leather trouser or great mini skirt and add a coordinating red lip and handbag. (P.S. For a bold statement, pair your red heels with bright pink, blue or orange).

Look 2: Talking Texture

Christian Dior shares that “You can wear black at any time. You can wear it at any age. You may wear it for almost any occasion” and we couldn’t agree more. It is undoubtedly the most classic and versatile shade when it comes to our footwear. But how do you keep a black heel interesting? Firstly, look for styles with added details—i.e the crocodile texture and gold buckle detail of The Buckle-Up Mary Jane. Secondly, it’s all about how you style them! We’ve paired this heel with trendy tights for even more texture (and a bit of warmth), a black mini skirt, cozy brown knit and a bold statement patterned coat. Try this look for work or weekend or switch it up by pairing the heels with a crop trouser and gold button embellished jacket.

What are your tips on transitioning heels into winter?

The key to transitioning your outfits between seasons lies in layering and fabrics. For Fall/Winter, add a turtleneck under a button-up or crew neck sweater; tie your knits over your shoulders on top of a blazer; add patterned, coloured or textured tights under your denim, trousers, dresses, skirts and shorts or throw on a statement coat.

Avoid linens and light summer fabrics and lean towards big knits, wool or cashmeres, velvet and corduroy. However, the most important way to transition your heels other than adding a sock or tight is by taking the right care precautions to protect them from the elements. This can involve protectant sprays, getting them resoled and taking them to be properly cleaned (this can help your shoes last 10+ years).

Julianne Costigan Poppy Barley

What heel styling trends are you seeing for Fall/Winter 2021?

This Fall/Winter season we are seeing heels being styled with socks and tights of all sorts. Ruffled, patterned, colour blocked, sheer and opaque, adding a layer underneath your favourite heels can be a great way to not only keep your feet a little warmer but presents an opportunity to reveal your unique personality and infuse your look with colour, pattern or texture.

Another way we are seeing classic heels taken to the next level through styling is with accessories. Try adding a chunky or delicate chain or pearl anklet to your ankle—this creates the appearance of a detailed heel strap. A shoe brooch added at the front or back of a heel is also a trendy way to add a little glam to your classic shoes.

Follow Julianne: @julianne_costigan
Learn about Julianne’s Digital Style Guides here.

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The Harley Heeled Sandal Ankle Size Guide

How To Measure:
The Harley Heeled Sandal: Take a tape measure and wrap it around your foot, right below your ankle bone as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 26 cm
5.5 26.5 cm
6 27 cm
6.5 27 cm
7 27.5 cm
7.5 27.5 cm
8 28 cm
8.5 28 cm
9 28 cm
9.5 28.5 cm
10 28.5 cm
10.5 29 cm
11 29 cm
11.5 30 cm
12 30 cm

The Esther Heeled Sandal Ankle Size Guide

How to Measure:
The Esther Heeled Sandal: take a tape measure and wrap it around your ankle, above the ankle bone, as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 23 cm
5.5 23 cm
6 23 cm
6.5 23 cm
7 24 cm
7.5 24 cm
8 24.5 cm
8.5 24.5 cm
9 24.5 cm
9.5 25 cm
10 25 cm
10.5 25.5 cm
11 26 cm
11.5 26 cm
12 26 cm

Belt Sizes

Natural Waist Measurement Typical Jean Size Belt Size for High‑rise Pant Belt Size for Mid‑rise Pant Infinite Belt Size
23-25" 23/24 26" 28" 1
25-26" 25 28" 30" 1
26-27" 26 30" 32" 1
27-28" 27 30" 32" 1
28-29" 28 32" 34" 2
29-30" 29 32" 34" 2
30-31" 30 34" 36" 2
31-32" 31 34" 36" 2
32-33" 32 36" 38" 3
33-34" 33 36" 38" 3
34-35" 34 38” 40" 3
36-37" 36 38" 40" 3
38-39" 38 40" 42" 4
40-41" 40 40" 42" 4
42-43" 42 44" 46" 4
43-44" 43 44" 46" 5
44-45" 44 46" - 5

Sizing Note: For the most accurate fit, measure around your body where you plan to wear the belt. Choose the closest belt size to that measurement.

Belt Diagram Accent Belt and Complement BeltThe Accent Belt, The Polished Belt and The Complement Belt size measurements start from the beginning of the leather to the middle hole.

Belt Diagram Infinite BeltThe Infinite Belt size measurements cover the entire length of the leather.

Belt Measuring Guide

Belt Measuring Guide

A - High-rise style:

If you plan to wear your belt around your natural waistline, wrap a measuring tape around the narrowest part of your midsection. Then, add 3” to determine your high-rise belt size.

B - Mid-rise style:

If you plan to wear your belt lower than your natural waistline, you will require a dierent size. If you have a particular pair of bottoms you intend to wear your belt with, wrap a measuring tape through the belt loops while in a relaxed position.

When wearing your belt in your preferred style, it should fasten in the middle hole. The belt will relax with wear allowing you to cinch it tighter, as needed.

If you plan to wear the belt in both the high and mid-rise styles, you have two options:

  1. Select your high-rise style and fasten it more loosely when worn in the mid-rise style.
  2. Select your mid-rise style and fasten it more tightly when worn in the high-rise style.