We got this request a little while ago from one of our readers…
Can you help suggest what to wear with a boyfriend blazer? I just got a slim, one-button wool boyfriend blazer (from Iisli – love it) and am not sure what would look best with it.
This is a great question, and we loooove Iisli. First, let’s have a brief review of different terminology — all of these types of blazers can be worn at the office, but very different rules apply.
Boyfriend blazer - So named because it’s as if you stole your boyfriend’s coat, this typically means a voluminous, boxy fit — see the picture of Mary-Kate Olsen, at left. This is actually the hardest look to pull off at the office, because you need to balance the boxy-ness of the jacket with every other element. We’d suggest it a pencil skirt or a tight shift dress — or perhaps even skinny trousers. Play around with layers, if you can — try a man’s shirt underneath it, with all sleeves rolled up. (These blazers never really attained “in” status — they’re a bit hard for anyone who isn’t MKO to pull off — which means that if you can do it you’ll be cutting edge. Work it!)

Boyfriend cardigan — This is an easier look for the office. The fit should be roomy on you, and the buttons will start lower down your body — generally rising no farther than your breasts. The length of the cardigan is long, also — certainly past your hipbones and sometimes even the top of your thighs. Unlike the boyfriend blazer, this kind of covering will be slim-fitting because of the fabric, typically a lux cashmere or thin cotton. These are great at the office over sheath dresses, or even trousers (when your top is otherwise slim). (If anyone is in the market for one, check out the $54 boyfriend cardigan from the Gap, pictured at right (click on the picture for the link). Play around with belts worn on top of the cardigan, also — either go very very skinny or very very thick and see how they work with you. You can also try using a brooch to close the cardigan in the middle, a la Michelle Obama.
Schoolboy blazer — Popularized by Balenciaga a few years ago, the schoolboy blazer is a cropped blazer (the idea being you stole it from your younger brother) that looks like it could be part of a private school’s uniform. Contrast on the lapels, sometimes even insignia, et cetera. These seem to be on the way out, in terms of fashion — we couldn’t find any of-the-moment examples — but if you’re still inclined, we’d suggest pairing it with high-waisted trousers (or regular trousers will do if you don’t have high-waisted ones — the wider the better).
Cable Blazer – In all honesty, we’re most familiar with wool sweater blazers from Iisli, which don’t really fit into any of the above categories — they’re slim-fitting and can be cropped or long. (We’ve seen them recently on HauteLook and Gilt Groupe, but can’t find them in any online store at the moment — which makes us sad because seriously, our two Iisli sweater blazers are two of our most favorite pieces. You can also try eBay, which is where the picture, at left, came from.) We’d suggest wearing these with pretty much anything you want to — trousers, pencil skirts, A-line dresses, et cetera, et cetera. We always like the look on the weekend with jeans — it dresses up a casual t-shirt, and it dresses down an overly sparkly/revealing camisole.

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That was my question, thanks for answering!!
The boyfriend blazer is actually slim fit and not boxy, so it is more flattering (I hope) than the MK-type ones. But given the longer length I still think skinny trousers look best.
I now share your love of Iisli! I bought a black boyfriend blazer and a sample regular blazer (shorter cut but not cable-knit) at the sample sale and loved them so much I mail-ordered the boyfriend blazer in grey as well. Only downside is that the sleeves come way too long, and the knit doesn’t alter very well (at least not with my tailor).
http://alltheprettybirds.blogspot.com/2010/01/smooth-operator.html