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The Blazer
Actual men's blazers, unlike "boyfriend" styles for women, are always going to be a bit boxy and slouchy on a lady's frame. The secret to making that look good, rather than sloppy, is to balance the oversize fit with neatly tailored pieces beneath. Also: always, always, ALWAYS roll up the arms! Otherwise your outfit—no matter how perfect—will instantly seem stiff and uncomfortable!
Pair it with a girly dress.
So long as the waist is emphasized (all that extra fabric on top of a shift style will seem bulky and shapeless), anything goes. I especially like the prepster pairing of navy and white with grittier shoes, like a pair of suede ankle booties. Think Spencer Hastings...not Spence.
Give the distressed denim/lacy top combo some polish.
Although the two pieces alone already work in a folksy, outdoor concert kind of way, the addition of a long blazer changes everything. The outfit swings from Coachella to Paris Fashion Week in a second, meaning you'll be able to wear it to flower crown-free parties, too. This look would also work with flats, though we recommend wear these lace-up sandal pumps if you don't mind the heel! It really drives the Carine Roitfeld homage home.
The Collared Shirt

Because this one is pretty hard to mess up, it's faster for me to tell you what to avoid.

1. Don't wear it open, '90s boy band style, over a fitted T-shirt or tank top.

2. Always roll your sleeves.

3. If you don't want to tuck, pair it with skinny pants—or plan on belting your waist. Otherwise, all that baggy fabric will overwhelm your frame.

Click through for white collar shirt ideas now.

Juxtapose it with a flowing maxi skirt.
But instead of tucking it in, leave a few bottom buttons undone and tie the two ends in a knot. This will give your outfit shape and structure in a non-fussy way. You should also roll your cuffs, at least just a little at the ends, because it fakes a better fit.
Make your cutoffs less casual.
Just tuck it in, throw on brick red lipstick and accessorize with buttery leather accessories. And, again, because this is worth repeating: don't forget to roll up your sleeves! Everything will be ruined if you don't!
The Undershirt

To make this work in your everyday wardrobe, you can't can't layer it the same way dudes do. There's just too much material to shove under another top! Instead, think of it like a blouse or T-shirt dress and you'll be just fine.

Click through for undershirt outfit ideas now.

Turn it into in a tunic.
However, to avoid an "oops, I forgot get dressed" effect, wear it with really sturdy leggings made of heftier material. I recommend investing in a cashmere pair, but wool, silk or high-quality cotton options would work, too; just make sure they're opaque. Then throw a long grandpa cardigan over your tee, slip into loafers or brogues and you've got yourself the most perfect weekend outfit ever.
Give your fancy pencil skirt some street cred.
It hits that spot between loungewear and cocktail party attire that our favorite street style stars always seem to get right. Finish the Fashion Week-ready look with bold look-at-me accessories.