I bat for Team Dressy, but typically wear very casual clothing on a Sunday when I work from home, run errands, catch up on stuff around the house and take our doggie Rosie for a walk. This is a typical casual outfit when it’s not too cold outside. On a colder day I’d have worn a turtleneck and boots, and popped on a scarf, hat, gloves and possibly a puffer coat. 

I have a very hard time feeling fabulous in a t-shirt no matter how I slice and dice it. But I fancy a black and white graphic striped tee and believe it’s a true wardrobe classic. I have precisely one T-shirt (if you don’t count the ones I sleep in) and this is it. Occasionally I’ll wear it layered under a blazer or jacket with a scarf so that just a hint of the stripe is visible. For the rest of the time I prefer to wear my striped T over a crisp un-tucked white button down shirt like a pullover. 

I like a boat neck T layered this way because it exposes more of the white shirt. I either pop the collar leaving a few top buttons undone, or I’ll completely button up the shirt as shown here. Sometimes, I button up and pop the collar because my giraffe neck enjoys the extra coverage. I’ve been treating my shirt collars this way since the ’80s and it still feels right.

I know I’m in the minority with my preference for a strict and buttoned up look, especially when it comes to wearing stiff button down shirts for casual wear. So I totally understand that the combination is not your cup of tea. But wearing a T-shirt this way makes it feel more like my style, and I’m extremely comfortable in the pairing. I also like the look of untidy cuffs, so I leave them to do their unbuttoned thing most of the time. 

For my casual style, I’m perfectly happy to wear uber casual items on the bottom half of my outfit like  faded jeans, rugged flat boots and fashion sneakers. But the top part has to stay fairly tailored and dressy. Layering the button down shirt is one way of achieving a dressier vibe, but I take it a step further by adding in a structured jacket like a blazer or cropped jacket. Here I’m wearing a short military jacket with a double zipper and fun printed satin lining. It’s made of a knitted fabrication so it’s soft and cozy like a cardigan. 

Although I bat for Team Skinnies, I still love to wear my bootcuts, keeping the hems as long as possible, just sweeping the surface of the ground. I also adore basic Chuck Taylor Converse sneakers and have several pairs in different colours. I find their white soles and laces absolutely magical and just don’t tire of the look. Also, I think it’s phenomenally cool that the exact same style of shoe can still look hip after many, many decades. I totally want to keep on supporting the legacy of the style. I do make my Chucks more comfortable by inserting an additional cushioning insole. 

I do not wear accessories with my casualwear other than a watch, wedding ring and specs. I’ll carry a handbag if I need to carry a wallet. A wool coat goes over the entire outfit and boy am I all bundled up. I’m wearing five layers on top and feeling adequately toasty. Yes! I like to wear jackets under coats for two reasons. First, the added warmth is fab when you have little resistance to the cold like I do. Second, when out and about, it’s nice to take off your coat and still feel pulled together because you’re wearing a structured jacket. 

I bat for Team Flats. One reason is comfort. My feet do not like to arch so flats or low heels are by far the most comfortable options. Another reason is practicality. I often dash around town all day at a fast pace braving the Seattle elements. All that said, I still like to wear heels because of their magical ability to elevate an outfit. I just have to be extremely careful when I select them. 

It’s amazing how many women share similar heel wearing challenges, most of which are rooted in some form of foot discomfort. Some find heels higher than one and a half inches agonizingly uncomfortable on the balls of their feet. Others get cramps in their arches. Some pinky toes are severely squashed no matter how wide the toe box, while bunions can cause immense all over foot pain. Well, between the needs of my own fussy feet and those of my clients, I could write a book on this topic. 

The good news is that there are great heel wearing solutions for Flats Fashionistas if you’re extra mindful about the design details of the shoe. I’ll run through those details so that you can prioritize according to the needs of your lovely feet. Since this is holiday season you may be thinking about buying a pair for someone else. In that case you might be able to use this as a guide.

Cushioning Comfort

It’s essential that all my heels have soft, spongy, cushioning insoles built into the foot bed of the shoe because that design feature relieves some of the pressure on the balls of your arched feet. For extra cushioning comfort, add a separate insole from your local drug store. The Sofft Ramona’s have been a life saver for ladies who have to wear heels all day. The Stuart Weitzman Forsures are even more comfortable because along with a cushioning footbed, there’s a soft width of elastic along the top of the shoe that stretches as you stride. It’s such a clever design detail! I suggested them to my client Karen who is wearing them with her leather dress, and she is thrilled with these pumps. 

Manageable Heel Height 

Heels don’t need to be super high. Unless I’m at a fancy function and can sit all evening, I like a one and a half to two inch heel because that height causes less pressure on the balls of my feet. I find that I can still walk fairly fast in a comfortable low heel, especially when it’s fairly chunky. Stuart Weitzman’s Puffystuff kitten heel is an example of a stable, dainty low heel, while Nine West’s Newkimmie is casual with a chunky low heel (Loafers are making a pretty strong statement next year just in case you were wondering about this particular style). 

Heels with Straps

Some of my clients complain that pumps fall off their feet. I usually suggest heels with some sort of strap to keep the ped in place. Mary Jane styles are a super solution, as are T-Straps like BC’s Big Country pumps. For something a little different, try a hybrid between a pump and an oxford, like Stuart Weitzman’s Midtime. Gorgeous shoe.

Boots Instead of Pumps

Heels can be made even more comfortable when you wear them with cozy socks. This is one of the reasons that I prefer to wear boots and booties than any other form of footwear. My Frye Taylors are wardrobe workhorses because of the manageable chunky low heel and brilliant fit. When I wear them with thicker socks, they are all day city walking shoes. But if you’re after a dressier and more classic ankle boot for the office, a simple sleek style like Stuart Weitzman’s Parttres are ideal. 

Oxfords and Shooties

These high vamped styles provide less coverage than ankle boots but more coverage than pumps. Heeled oxfords like Clarks’ Palmyra Erin and shooties like Fidji’s Alea E872 can be worn with skirts and dresses as well as jeans and trousers. I really enjoy these types of heels because they tend to look more playful than a classic pair of pumps, AND I can wear them with comfy socks and under jeans.

Wedged Heels

Some of my clients find that they can wear a higher heel height when the style is wedged. I have definitely found this to be the case and can wear up to two and half inch wedges, whereas I often battle to traipse around all day in a two and half inch chunky or narrow heel.  Gentle Souls Ridgual wedged booties are as cute as they are comfortable because there is lots of room in the toe box. Amalfi by Rangoni’s Dante style wedge is narrower and more streamlined, but has the added benefit of an elastic upper that moulds to the shape of your foot.

Platforms

Platforms often allow you to wear a higher heel because they minimize the arch of the foot. For example, the Marlo from Kork-Ease has a high three and a quarter inch heel, but it’s one inch platform makes it feel more like a low two and quarter inch heel. La Canadienne Geralda’s two and half inch heel is platformed by five eighths of an inch, so it feels less than a two inch heel on the foot. The wedged style makes it even more comfortable.

Arch Support

Some of my clients also require arch support to prevent foot pain. Footwear brands like Taryn Rose and Dansko provide substantial arch support, but if that’s not sufficient, adding in your own supportive orthotic will probably do the trick. Size up half a size when inserting an orthortic. Taryn Rose’s Kelly is a particularly great choice because it’s wedged with an elasticated vamp, while Dansko’s Rhianna has a platformed advantage. For the longest time, I couldn’t understand why these footwear brands do not work for my feet. I eventually realized that my arches do not require that much support, and over supporting them is actually uncomfortable. 

While the specific examples I have used might not be to your taste, hopefully they illustrate the important design features that will help you find comfortable heeled footwear. In addition, remember that soft leather and a roomy toe box make a shoe more comfortable straight off the bat. And that some shoes can be stretched if they are snug in a particular area.

I’ve mentioned a few brands here that generally make comfortable and good looking heels, but there are plenty more. Brands like Chi Mihara, Anyi Lu, Fitzwell, Reiker, Paul Green, Miz Mooz, Cole Haan, Fly London, Tsubo, Fluevog, Aerosoles, Aquatalia, Naya, Born, Naturalizer, Dr. Marten, Pikolino and Donald Pliner are often worth trying because there is a good chance that they will keep your fussy feet happy. 

Please use the comment section to suggest other brands that make comfortable heeled footwear. Also mention what it is about their designs that makes those heels comfortable. This Flats Fashionista is always interested to hear more about comfortable heeled footwear options.

You have your set of “go to colours”, but at the same time you’re also very attracted to a “new” one. It’s like you suddenly discovered the brilliance and flattering effects of that colour and now you’re deliberately looking out for wardrobe items that use it.

For example, I have always loved, and continue to love bright tomato red, citron, lime green, shocking pink, and turquoise — along with black, white and cream. But over the last 18 months ink blue and rich navy blue have been growing on me. In the last 6 months I have been head over heels for these colours. The blue is by no means a replacement for black. In fact, I adore ink blue together with black. 

When was the last time you had a new favourite colour?

More and more designers are mixing it up on the runway with wildly clashing patterns. Some of the patterns are in the same colour palette, which helps create a harmonious visual, and then there’s the rest. The trend is what I call the “chopped salad look”. Whether that tantalizes your taste buds depends on your stylistic preferences. 

The two outfits above from Zara are particularly advanced examples of pattern mixing. To my eye, these patterns clash in such an extreme way that they actually work. The more muted colour palette helps gel the patterns together. This is not a look that I would wear, but I can see it working quite well on a few of my clients and some of our forum members.

The second two examples aren’t as crazy as the first, but they are still bold and daring. For myself, I prefer the more graphic vibe of these mixed pattern outfits because the effect is more crisp and simple. I adore the combination of the rugby stripe and nubby tweed in the J. Crew outfit and would happily wear that with a pair of flat oxfords. 

I wholeheartedly believe that advanced pattern mixing is a brilliant and fun fashion forward concept that allows you to flex your creative and daring style muscles, AND make the most of your wardrobe. Think of all the extra outfit combinations you could sport if you fearlessly mixed up most of the patterns in your closet. But in the same breath, much like messy hair, advanced pattern mixing is hard to pull off. There is a risk of looking unstylish and clueless about patterns. The outfit components have to be just so, making the overall effect chaotically cohesive. 

Does advanced pattern mixing work to your eye, if not for you but on someone else? Can it look attractive in an arty and dramatic way? When does the effect work, and when does it flop? Or do you find the chopped salad look distasteful, no matter what.