Choosing Boots: 3-point checklist

1. The colour and style

A minimun boot wardrobe should include a pair of dressy leather (or suede) boots in a heel height you are comfortable with, in a neutral colour. Comfort, however, is not the only consideration when choosing a heel:

• Chunky heels are necessary to counterbalance an outfit with a lot of volume (either wide-legged pants, smock dresses, or billowy anything). They are also more comfortable for work.
• Leather covered heels are dressy, stacked (wooden) ones are not, more so if their colour contrasts with the leather.
• Petite caveat: very high heels on short women look out of proportion, medium height, slender heels are better.
• Blatantly equestrian or hunting styles should be avoided, especially if you are also wearing riding pants unless you are actually doing either: it will look like you have lost your horse.
• Avoid thick platforms, you are aiming at a fashion proof pair that looks good for work and play. 
• You may pull off mid-calf boots with just above the knee skirts (although not for work), but it is NOT a flattering length for the legs. Under trousers that's obviously not a concern.

Rembember that neutral (a colour that goes with most of your items) does not necessarily mean black. If your wardrobe is full of browns and grays, your neutral would be brown or beige, or even  some shade of gray.

Styling tips for boots: Basic black dressy boots by Caroline Grant. [Style: Modern Classic].

Nine West Justright Boots / Dolce & Gabbana Cropped Houndstooth Jacket / Somerset by Alice Temperley Tie Neck Blouse / Coast Hope Pencil Skirt / Hispanitas Handbag / Tory Burch Opera Length Gloves / Mercy Delta Exposed Branches Scarf / Indiska Rory Hat / Victorian French Jet Earrings at Trocadero (antique) / AK Anne Klein Round Dial Leather Strap Watch / NARS Lipstick Funny Face / MAC Nail Lacquer in Steamy.

Styling tips for boots: Basic black casual boots by Caroline Grant. [Style: Modern Classic].

Omar Knee High Boots / Phase-Eight Imogen Quilted Coat / People Tree Bridget Culottes / CC Pleat Edge Serape Cardigan / Ben Sherman Shirt / Totem Salvaged Leather Trimmed Cotton Tote / Battery Park Buckle Hat / Linea Pelle Sliced and Perforated Belt / Mango Cotton Printed Scarf / Mango Leather Gloves / Zara Voigt Flower Earrings / Iman Luxury Moisturizing Lipstick in Iman Red / Estée Lauder Nail Lacquer in Enchanted Garnet.

2. The fit

The most flattering boot length is above the widest part of the calf. Boots should mold to your ankles and calves, not buckle and sag, or create a gap at the top.

• If you have thicker than average calves, look for boots with stretch pannels, either on the sides or along the back. In general, avoid boots that are completely made of stretch material: it is better to choose a style that offers tailored lines in leather and stretch. Pull on versions usually allow for thicker calves. Avoid styles that dig into your flesh. Don't choose a style hitting at mid-calf, that shortens the leg and makes it wider.
• If your calves are thinner than average, watch out for excessive gap between your leg and the boot. Choose a narrow version or a completely stretch one.

Styling tips for boots: Basic beige dressy boots by Caroline Grant. [Style: Urban Tweed].

Baukjen by Isabella Oliver Romee Coat / Hobbs Unlimited Cloud Flower Velvet Tunic Dress / Burberry Orchard in Check Jacquard Handbag / Söfft Broadway Shoes in Snake Print Cognac / Black Lily Spar Jennifer Silk Scarf in Cinnamon / Kamene Leather Cuff Gold Tiger Eye Bracelet / Iosselliani Tiger Eye's Fringe Earrings / NARS Lipstick in Autumn Leaves/ Revlon Nail Lacquer in Valentine.

3. The comfort level

Before buying a pair of boots, walk around on the floor, also over a non-carpeted area. Check if the insole includes padding, the best brands do.

Check your silhouette in a body length mirror and ask for the shop's returning policy before buying!

Styling tips for boots: Mid Calf by Caroline Grant. [Style: Urban Tweed].

Clarks Lowrie Asha Brown Boots / Hobbs Corby Coat / Michael Kors Shimmer Sweater / Burberry Prorsum Tweed Trousers / Orla Kiely Punch Wallflower Handbag / Target Merona Brown Buckle Felt Hat / Aspinal of London Gloves / Mango Animal Print Scarf / Kate Spade Posey Par Statement Necklace / Estée Lauder Pure Color Lipstick in Red Tango/ Revlon Nail Lacquer in Valentine.

MORE?

• Essential boots you should own.
• Styling tips for boots with trousers.
• Styling tips for boots with skirts.