The strong influence of ‘90s fashion has brought back square-toe footwear. Trends stick around for years and items seldom date these days, so we’ll be seeing square-toe footwear for a while. Another contribution to fashion’s gigantic melting pot of sartorial choices. 

There is a wide variety of square-toe footwear. Toe boxes range from VERY square and chunky shapes, to more refined versions, with less square snip toes or round square toes. Snip-toe styles are pointy toe boxes where the tips have been “snipped off” to create a square shape. The collection below shows examples of square-toe footwear.

Here are some outfits worn with square-toe footwear, and most of the examples are boots.

I’m an ‘80s pointy-toe footwear gal at heart, but I like square-toe footwear too. I especially like square toes on those who find the style comfortable because the shape matches the contour of their feet. Some of my clients and friends wear square toes with the best of them. I’m thrilled they can stock up on their favourite look because happy feet are stylish feet.

For my own style I like refined square-toe closed shoes, and love a snip toe. Extremely square toes are generally too short for my long toes. Long snip toes tend to be a better fit. Long snip toes are also visually more elongating in outfits. I seldom like wearing open shoes with square toes because I have pointy feet. The shape of my pointy feet — which is on display in open shoes — doesn’t follow the shape of the square soles. Sometimes this looks odd to my eye.

Over to you. Do you like wearing square-toe footwear? Do you find it comfortable and flattering?

Here’s a selection of winners for those who are setting aside their sneakers and slippers for casual and smart casual boots, and their Athleisure jackets for very soft and cosy toppers. Some of the items are going for a song on sale. 

1. Sam Edelman Daysi Kitten Block Heel Booties

These are one way to go if you like a refined and on-trend square toe. The colours and patterns are interesting and a little different from the norm. Both snake prints are unusual and maximal. The block heel is manageable and chic. Lovely on the foot. They are fairly comfortable, although a little stiff at first. The footbeds are not super soft unless you add a cushioning insole. Not a wide boot. Personally, I found them too wide for my narrow ankles, but I am sensitive to the “stem-in-a-flower-pot” effect. You might not be. Some of the colours are going for $53 and $64.

2. Nic & Zoe Toppers

Nic & Zoe toppers are frequently soft, knitted, texture-rich, and semi-structured. For that reason they are very comfortable, and tend to mould to the contour of your figure and work on a range of body types. They are often available in extended sizes – thank you – and are easy to layer. If structured, stiff, and sharp woven toppers are not your thing, check out this brand.

3. Boden Clarendon Knitted Jacket

This navy darling earned a place in my wardrobe because it’s super cute in a Modern Retro way. Click the link to get a better sense of the style because this photo does not do it justice. I LOVE the casual glam vibe, the drama of the faux fur collar, and the gold trim. The lantern sleeves are pretty, and the fit is fluid. Very comfortable, and my version of a cardigan that I can also wear at home. The fur collar is high so it’s best on a longer neck, but it can be removed. I hope it does not pill soon.

4. Bernado Ecoplume Lust Packable Icon Jacket

I haven’t seen this in person yet, but the fit and colour look delicious and unique. Bernardo makes great outerwear so I do trust the brand. Ecoplume is a recycled-polyester insulation that is made from 100% recycled plastic bottles, so eco-friendly too. Soft, semi-structured, sleek, modern, fun and goes up to 3XL.

5. Miz Mooz Louise Slightly Slouchy Bootie

This bootie is for Team Stompy Steampunk Lite. Miz Mooz is an Israeli brand that is head-quartered in NYC. We met the team in Manhattan ten years ago and it was a lot of fun. The brand makes very comfortable and good-quality casual footwear in fun colours with a polished dystopian edge. The footwear wears well and is robust. The leather is very soft and moulds to the foot. I have found that their sizes run short in the toe box for my long toes, and sizing up does not always work. But it’s worth taking it style by style.

I see this practical layering combination quite often and think it’s clever. To my eye, it can look interesting and swish too. Layer a VERY thin puffer vest, jacket, or coat under another item of outerwear for warmth. That way you’ll stay insulated, create layering interest, and cover most of the puffer part of the outfit if sporty puffers aren’t your cup of tea. You’ll need an extremely compact, soft and light puffer, like something from Uniqlo’s Ultra Thin Light Down Collection, or ThermoBalls from The North Face. Here are some examples.

The layering strategy is highly effective at keeping out the chill when wool coats, raincoats, and the like aren’t warm enough. Of course, you could simply choose one layer of outerwear that suits the outside temperature and leave it at that. But it’s good to have options. At some point, the layering combination might strike the right note.

For comfort, you’ll need to layer the compact puffer under a sufficiently roomy jacket or coat. If hoods aren’t your thing, choose a puffer without a hood. That said, in the wet Pacific North West, the addition of the hooded puffer means you will always have cover in the rain. If puffers with sleeves are too warm, try layering a puffer vest under a jacket or coat. That way you’re insulating less of the body on the off chance that you’ll overheat. The vest means you don’t need to worry about tightness on the sleeves either. Here are some examples.

You don’t need to keep the lengths of the layers the same. You can wear shorter puffer jackets and vests layers under longer coats. Look how well these gents sport the look. And for a more avant-garde effect, layer shorter outerwear over longer compact puffers. You can choose to keep the colours between the puffer and the next layer of outerwear tonal or high contrast. Low-contrast and tonal layers will look more like you’re wearing one coat instead of two.

Here’s a Sporty Luxe and high-contrast example of layering a puffer vest under a black suit. Of course, you can create a low contrast with the puffer vest if that’s more your cup of tea.

I sometimes wear my bright red ThermoBall compact puffer under my bright yellow Paddington Bear rain coat because although the raincoat is perfectly waterproof, it isn’t warm. The combination is MUCH warmer. The layers are very comfortable, although I do resemble hotdog fixings. That’s why I’m toying with the idea of getting a cream or navy ThermoBall.

Does this type of outerwear layering appeal to you?

Everybody & Everyone is a casual and smart casual clothing brand that takes its sustainable and ethical practices extremely seriously. So much so that you can shop for items online under categories like “100% Recycled,” “Organic,” “Biodegradable” and “Eco-Innovative.” You can also shop from categories like “Odor + Spill Proof,” or suitable for “Friday Night In” and “Work From Home.” Their category of “Little Eco Things” is worth a look too.

The brand offers a fairly size-inclusive assortment that runs from US00 to US24. They specialize in offering elevated and great quality everyday essentials that aim to make life easier, while at the same time better for our planet.

Everybody & Everyone uses material science and smart design to maximize the life of clothes and minimize our negative impact on the planet. Each of their raw materials is measured for its sustainable footprint. For example, in order to reduce carbon footprint, most of the fabrics used are produced near the factories that makes them into clothing in order to save energy and resources.

The brand also teams up with other eco-conscious companies to produce their items. (Coincidentally, Naadam, who we spotlighted last month, makes their knitwear.) They also work with a tree planting project to offset unavoidable carbon emissions. For every one of Everyone & Everybody’s shipments, the company that ships their products purchases one tree for $1 from a non-profit organization called “One Tree Planted” on their behalf. This raises awareness on why trees are so important, and reduces their carbon footprint in a more subtle way.

Items are made of organic cotton, linen, silk, hemp, viscose, eco-friendly cashmere, tencel, fermented sugar fibres, biodegradable trims, and recycled polyester and nylon. The brand also offers a way to recycle our own unwanted clothes if we send the items to them. They pay for shipping in the US, and make sure your items are turned into things like insulation and carpet padding instead of clogging up a landfill.

I see the brand working particularly well for a casual, minimal style. The simplicity is versatile and has a quiet presence. Items are well-made, and intended to last longer than regular essentials, although they are pricier.

If you want to cosy up for Fall, work from home in eco staples, or upgrade your loungewear, take a look at this brand. Their novel odor + spill proof collection is awfully practical. The Little And A Lot Pants look fab because they have an adjustable waist and length, are made of stretchy fermented sugar fabric, and are crinkle-free. Sweet! If they came in a pattern or colour other than black, I’d be trying them.