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.
