After reading all the interesting suggestions in this thread, I felt inspired to dress a little bolder today than I did yesterday. I've added photos to illustrate how (unfortunately low quality, but I hope you get the idea).

#1: Yesterday I wore a cropped mustard pant with a blue pinstriped shirt. I added a gray tweed blazer and red patent leather low wedges. All items are nice by themselves, but the combo felt meh.

#2: Today I wore a classic dark wash jean combined with a black blouse with ruffles. I topped it with a taupe leather jacket. I resisted the urge to add dressy shoes, and added blue Con's instead. The shoes made the outfit much more fun, and I got so many compliments today!

Lesson learned: I need to add an element of surprise to my outfits, either as an accessory, or a deliberate mismatch in color or style. Then it will feel more like ME. Outfit #2 works for me because the Con's are very casual while the blouse isn't. That makes the outfit more interesting and less predictable. See detail in #3.

What do you think?

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