Late to the party, but I hope I can share the few things I've learned and noticed since deciding to dress like *me* at the office.
There is one particular woman I work with - she is client facing and and always looks professional yet stylish. She is NOT an UWP, but I think the basic, formulaic principles or her work outfits can still apply:
- Suits. Fun suits. I swear she has a closet full of them, like any normal banker, but they are all current and feel fresh. Gray with white pinstripes. Textured black. Double lapels. "Corporate" colors, but cheeky in either cut or fabrication (MaryK hit on this, too). I don't think hers are greatly expensive, because I get the feeling she refreshes often.
- Blouses. I don't think this person ever wears a crisp shirt. She doe scoop necks, soft and silky blouses. I think this also helps take away from the "stuffed shirt" feel of the banker look.
- Jewelry. I don't know about your clients, but even older, conservative ladies in BH can appreciate some fab jewelry without thinking the wearer will funnel their estates into pork futures.
My own strategies:
- Boots. Tall boots, short boots, booties. They carry a lot of personality for me.
- Jackets. I've always loved jackets, and now they've largely replaced blazers for me. I still have some blazers, too, but my AT jacket with the leather throat latch, for example, feels more right.
- Prints and textures... tiers, stripes, dalmatian hair... even though I'm still technically wearing a pencil skirt and button front, it feels more soulful.
- And I think the most helpful thing to me has been to look at the whole picture and ask myself if it feels UWP. Do I need more warrior? Should I swap the blazer for a leather jacket? Is it professional enough? Should I wear a button front instead of a knit top?
- The other thing I like to do recently is have professional "stand ins" for my favorite casual items. Blue BB shirt stands in for denim shirt/jacket. Skinny cords stand in for jeggings. Aviator jacket stands in for utility jackets.
I love the idea of your bespoke suit, too. Perfect fits are always stylish, and I think the menswear vibe transcends trends because it is truly your style. That will be the Urban Professional part of the outfit. Add a little warrior and perhaps some princess color, and you'll be in business (so to speak).