Herewith, the Miles Standish Goes to Work Millennial collection. With just the tiniest bit of boomer street cred, And no blinkin’ irony.

Boring basics all French girls have, 100% cotton poplin, $55, ethically sourced from Everlane, a millennial-preferred company. See the factory:
https://www.everlane.com/factories/tailored-shirting
http://www.bintroo.com/10-boring-basics-french-girls-always-have-handy/
https://www.everlane.com/products/womens-relaxed-poplin-shirt-white

60% cotton, $30 on sale.
https://bananarepublicfactory.gapfactory.com/browse/product.do?pid=575647001&rrec=true&mlink=5050%2C12413545%2Cbrproduct1_rr_1&clink=12413545

classic bass weejuns, diane cut, in black. $89
https://www.ghbass.com/product/diane+original+weejun.do?sortby=ourPicks&from=Search&selectedOption=200391

with the white blouse, black pencil skirt, and bass weejuns, a farm to table ethically sourced scarf, with millennial provenance carefully spelled out. visit the rajasthan work shop.
https://www.blockshoptextiles.com/pages/process
$120, 75% cotton, hand printed, non-toxic dyes.
https://www.blockshoptextiles.com/collections/scarves/products/ribbon

a ring that looks like it hurts, again, farm to table from an earnest online artisan. with an earnest online statement.
https://www.lilarice.com/about
https://www.lilarice.com/all-products/break-ring

$6, pure poly, black lace footie with the bass weejuns
https://us.shein.com/Solid-Lace-Invisible-Socks-5pairs-p-769545-cat-1899.html

Riffing on reporter Mike Schmidt’s athleisure wear jacket worn with starched shirt and tie. Athleisure a huge millennial trend.100% poly shell, $29
https://www.fullsource.com/port-authority-1106801/?keywords=women%27s+jackets

$24 and 100% cotton chambray shirt, the blue version of which gave blue collar workers their name.
https://www.fullsource.com/port-authority-lw380-light-blue/

Levis 501s button fly jeans. Mens’. Black. 100% cotton. Because the women’s jeans industry is exploitative and basically bullshit. And you can fit your millennial ass into these.https://www.amazon.com/Levis-Mens-Original-Fit-Jean-Rinse/dp/B0006MZHZK/ref=sr_1_15?keywords=levi%2B501%2Bjeans%2Bfor%2Bmen%2Bbutton%2Bfly%2Bblack&qid=1561486433&s=apparel&sr=1-15&th=

A very hip redo of the Dr. Scholl’s platform sandals of the ’70s, frequently worn with rainbow toe socks. Birkenstocks are for revanchists. Dr. Scholl 4eva.
https://us.asos.com/asos-design/asos-design-foolish-chunky-flat-sandals/prd/10924022?channelref=product+search&mk=abc¤cyid=2&ppcadref=753857711%7C57945280935%7Cpla-656374336034&affid=14174&_cclid=Google_EAIaIQobChMIsaWr77aD4wIVhJ-fCh19ow9mEAkYCiABEgLpCPD_BwE&gclid=EAIaIQobChMIsaWr77aD4wIVhJ-fCh19ow9mEAkYCiABEgLpCPD_BwE

Millennials wear socks with their Birkenstocks. Hip ones wear these with their Dr. Scholl’s platform sandals.100% cotton, $12 for three pair
https://www.vermontcountrystore.com/buster-brown-ankle-socks-3-pairs/product/53880?utm_source=google&utm_medium=paid+search&utm_campaign=pla&sourceid=7SPFGPLA&gclid=EAIaIQobChMIvvHMiruD4wIVE8JkCh3BhwAZEAQYAyABEgISUvD_BwE

A little pizzazz, for God’s sake. Please. $15 pearls woolworth’s doesn’t sell, to go with the chambray shirt and and the 501s.
https://www.etsy.com/listing/620034149/30mm-ivory-pearl-necklaceplastics-pearl?ref=pla_similar_listing_top-3

You could dress like Elvis or Frank Sinatra or Fred Astaire or Louis Armstrong in the olden days and still get a job. Petticoats and plaids, not so much.
I think of Julia Louis-Dreyfus’ wardrobe on *Seinfeld* (1989-98) as the hip fashion template for ’80s working girls. It was very vintagey — the ’30s dits midi, two-tone swing-dancing oxfords, a jean jacket. No Tammy Faye shoulder pads or claw bangs.