I love this time of year for the opportunity it offers us to reflect and to consider where we want to go in the year ahead. Thanks to Angie and others who have started posting your thoughts about this. Your thoughts spur my thoughts and that is a gift.

Here are some of my favourite outfits of 2016 and my reasons for picking them. I apologize in advance for the photo quality of some and also for the length.

#1 is a spring outfit showcasing my new blue moto jacket, a long sought item that has become a workhorse. It's very soft and pliable, which makes it a good jacket for indoors and out.

#2 Most of my photos date from after my hair transition. Switching to a silver pixie was the best and most important style decision of my year. As Angie often says, everything follows the hair. I like this outfit because I adore the feel of the dress against my skin (silk) and also the cut.

#3 As with #2, I love how the hair brought new life to an older item. I learned that black and white patterns are now my friend as long as the scale is right.

#4 This outfit combines new with old (something I love) and showed me that with my natural hair colour I can do higher contrast than I used to find flattering. It was super comfortable in sticky heat.

#5 I owe LisaP thanks for finding this fun top at the Bay. It was such a hit for me this summer. The over-layer was its own "3rd piece."

#6 I adore CoH jeans and these are no exception. Silver has become a core neutral in my closet. Grey is very flattering, of course, but I find I need to combine it with white or ink, or else I feel "lowered" in it -- however kind it is to my skin tone. I need some contrast or brightness to feel like myself. Silver amps up the "bright" in grey.

#7 How could I not feature the controversial denim culottes? They're actually a bit more like a wide leg flare than a culotte, I think. Anyway, I enjoy them. I have successfully worn them with tall boots in the cold as well. Score!

#8 This may not be high fashion but it is so, so me, and pretty representative of my "at home" or casual travel style. Super comfy CoH jeans (cropped), super comfy Ecco sneakers (walked 10 miles in them that day), older LL Bean Mariner sweater, great bag. Love.

#9 Hard to see, but I'm wearing a silk shirt (again, the feel against the skin!), burgundy Dres (fit is sublime!), great bag, great booties. Silver belt. Simple but a bit luxe. I had a Theory trench to top it. The day was rainy.

#10 Aforementioned CoH white crops and Ecco sneakers and a denim shirt in dark blue -- much more flattering now than muddy chambray.

#11 This was an Annie Lennox inspired outfit that I wore to a WritersFest event -- so much fun. With my grey hair, black has earned a new place in my closet. I still plan to keep it quite minimal, but I won't be shying away from it as much.

#12 How could I neglect the famous gilet? Love this piece so much, although I have to confess it has not yet had many wearings. Our climate and my casual lifestyle are largely to blame. I'm not worried, since it will have long wardrobe longevity. Wore it with a fave pair of jeans and a silk shirt here.

#13 This outfit showcases my love of new trends. Finally found a pair of wool culottes that work well. Also combined with older pieces and great new red booties.

#14 Here's what I wore on Christmas Day -- glammed up denim, as per Angie's ensemble. With my grey hair I find I can wear a wider range of reds, from burgundy through to cranberry (my old favourite), true red and even bright tomato. This one is a bit on the blue side but close to true.

Overall...short grey hair adds a bit of drama/ boldness, which seems to call for greater drama/ boldness in kind — either via contrast, depth/ brightness of colour, or cut. So my favourite outfits usually showcased one or more of those elements.

I feel like I need a new style moniker but I haven’t had much luck developing one yet. “Urban prince” seems a bit tomboy for this leg of my style evolution. I considered “glam gamine” (Viva’s) but it seems off, too. I’m more 60s mod than 70s glam. I do love me a great flare jean and a midi skirt, but the old romance of the boho dance has never really been mine.

I'm still tweaking the hair a bit. I haven't quite found the exact style I want for it. A bit longer than its first iteration, and a bit shorter, maybe, than I've been wearing it of late. The most recent cut is close, but not quite right. Suggestions gladly taken.

Thanks for reading and looking! I'd love to hear your thoughts. And I look forward to reading about others' style journeys.

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Gingham Shirt
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Club Monaco
Norra Silk Dress
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