After starting my career in ill-fitting, stuffy dress shirts (similar to this “before” top), I swore off collared button-downs for a while. Only in recent years did I discover how the right material or details -think pretty silk, chambray, or prints – can make these shirts stylish and fun to wear.
I got this top for 50% off thanks to Elle‘s helpful sale tweeting last month, and love the plaid crested pocket (pictured further below; possible DIY idea), contrast collar/cuffs, and textured fabric. The site describes these shirts as chambray, but I feel the material is more like an oxford weave. It’s a good shirt for wearing un-tucked over jeans, or to work tucked into skirts or slacks. An XS fits casually loose on me, and the sleeves are not excessively long. Measurements of an XS: 17.5″ across armpit, 13″ across shoulder, 16″ across waist, 22″ approximate length, 22″ sleeve length. 
This custom map skirt from the talented SewPetiteGal remains one of my most special pieces. I can’t wear it too much as it’s such a recognizable piece – but every time I do, it manages to garner new compliments. I hope she has time in the future to open up her Etsy store again, so we can access more of her beautiful creations!
I love the versatile camel color of this J.Crew blazer, but these photos illustrate one of my biggest issues with it. The wool and lining are very thin, especially on the sleeves, and always looks crinkled from the slightest arm movement. The wrinkles don’t stay, but are just present. I’m not sure if other owners of the wool schoolboy blazers have experienced the same issue. 
I wore this outfit a few weeks back on a warmer day, and have been looking for the right tights to stretch it into another season. I’m thinking dark navy hosiery paired with same-colored pumps will be a good alternative to the standard black with black. Now if only I can find a shade dark enough so I won’t look like a smurfette!
PS – Ann Taylor’s current promo is 40% off all full-priced shoes, no code needed. For those who already own their classic “perfect pumps” (loving the seasonal dark jade in suede) and want the same comfort in a varying style, I’ve become a big fan the block-heeled pumps (closer photos here). They are sturdy without looking too matronly, and I’m enjoying not having to pull stuck thin heels out of sidewalk cracks.
Thanks! Just got some from Talbots with their 40% off sale, but will check out F21 if these don't work out.
Elissa – The cobbler can "patch" it with leather paint or something to make it look better from afar, but it never really is the same again.
Janki – Shirt tucking isn't usually an issue for me, but sometimes I've tried keeping it inside underwear or more fitted shapewear (but then you do run the risk of the top of the shapewear or undies getting pulled out above the skirt/pant waist line…eeks!).
Thank you – I sleep with it in a loose bun, and it's hit or miss in the morning!
I love your style! And your clothes fit so well, I'm inspired to start getting my clothes tailored and DIY easy alterations. Does your blog have an instagram account by any chance?
You are so gorgeous. I saw your video on Youtube once about styling hair into a bun and today, I happen to land on your blog page. I call it divine intervention. I will stay tune to your blog from now on. Love lots!
love the schoolboy blazer
supermodeltall.blogspot.com
jean, are you picking up anything from the ann taylor 40% sale items event going on right now? just made my haul and was wondering if you knew about it too! 🙂
What a stunning skirt! I've been looking for a map-print skirt for so long – so happy to see they actually exist!
Kate xo petite-adventures.blogspot.ca
Your hair looks amazing in the photos! Besides the wrinkly sleeves you pointed out, thus is one of my favorite outfits on you!
I love how you matched our jacket to your bag, Jean! Very stylish!
Just curious, what is the building that's in the background of the shoot? 🙂
Hue makes a dark navy tight that is very nice. I wear navy to work quite often, and this one is the best I have found!
In Canada you can find the brand at The Bay and Legs Beautiful… not sure about in the US!
Blazers get my MVP petite pick. Good find!
Gorgeous! Love the hair too.
Very chic blazer, the detailing is very nice!
Amazing outfit, that skirt is so unique! Love the colour of the shirt as well, really nice combination!
Jean, I noticed the wrinkle issue on this jacket as well, and didn't keep mine because of it. I have 2 schoolboy blazers. One is red in felted wool from last year, and I don't see the problem; the other one is the navy jacket which comes in a different texture. No problem there either. I think this jacket looks wrinkly because of the fabric (felted wool) and the color combination. The jacket I bought (twice) both had a problem in the front – one flap had trouble laying flat, and i think they were both on the same side. I really love the color of this jacket though despite all the issues.
amazing outfit!!!!!!
♥The fashion witch
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That is a fabulous skirt! SPG is super talented and love the fabric print. I like how youve paired it with the blazer and the purse matches too!
That skirt is fabulous, and matching your bag to your jacket looks well-coordinated and less expected than matching it to your shoes. Love it!
I've been following your blog for a few weeks now, and I consistently adore your outfits and tailoring tips! I've gotten a bit lazy in my work attire (all of my favorite pieces seem to need a hem here, a button there, and I can't stand the thought of taking such simple fixes to my tailor when I have a perfectly good sewing machine), so this has been the perfect kick-start for me to put some thought into my outfits again 🙂
I feel terrible pointing out a little typo the first time I leave a comment, but it's the only one I've ever seen in your writing, and since you seem so attentive to detail and precise in crafting your entries, I thought you might like to know: "managers" ought to be "manages." Cheers!
Amazing outfit! I love everything about it!
I've had a cobbler fix them. I tend to get the back of the heel nicked a lot. I must be a clumsy walker. It's not that pricey, about $10 or so.
These block heels are great! I have stayed away from them since they remind me of the heavy heels I used to wear in the late 90's. With my scrawny calves I must have looked silly. These look very stable and fun. One of the things I don't like about thin heels is that often I get comments from male coworkers (if we are walking somewhere) about my feet hurting. They usually don't, but still I don't want it to LOOK like they do.
Question: How do you keep your shirt so well tucked? Mine always bunches up.
Funny you mention dark navy tights since I just solved the same problem! (I used to have bright blue tights from Delias…but never knew what to do with them). Forever 21 60 denier tights in navy are opaque but quite dark and classy.
You look great! The first time I saw this skirt, you wore it with the peplum attachment and I thought it was a fabulous piece then; today's ensemble showcases this cool skirt very well. Great look!
Tese
afashionforwardmommy.blogspot.com
Amazing skirt!
Check out my blog where I already posted my second issue of my magazine!
Blog:www.gemmamonclus.blogspot.com
Love,Gemma
A very academic outfit! Lovely, as always!
*whoops meant geography
You look like a very chic geology professor! I love it!
So cute! I wish they still had the color combo of your top! 🙁
-Stephanie
@LaminLouboutins.blogspot.com
Such a cute outfit! I think your brown AV booties + mustard tights would look great with this outfit.
You look so classically chic! I love this skirt, SPG is so incredibly talented! 🙂
xo, Yi-chia
What an awesome skirt! Super clever design and you matched it perfectly with the rest of the pieces!
http://fashionedible.blogspot.com
Absolutely head over heels for that skirt! How cute! Is she going to be selling them?
xx Lynzy
http://www.sparklingfootsteps.com
Beautiful! Looks like Harvard campus in the background 🙂
Such a classy look! What a great skirt!
http://www.beautyandbows.com
While short, I'm not particularly petite but I simply MUST follow your blog as I am so impressed at how well everything is tailored to fit you. I really must start investing in items that do the same for me!
Awesome skirt!!!
Xo-L
simplylowcountry.blogspot.com
Love your outfit!! That skirt is too pretty!
With Love,
Ashley
ASassyWoman.com
Beautiful, love the styling and the photos are perfect!
Your last line actually brings up a question I have – when you get your heels stuck in cracks, does the leather ever come off/get ruined on the heel? (It's happened to me a few times) If yes, is there a way to fix it or do you just retire the shoe for good?
Thanks!
Great skirt you look,great.
Xo
Rachelle
http://pinksole.com
such a cool skirt!!!! you really pull off this smart look!!!
xoxo jenna
http://thepetiteblog.blogspot.com
Awesome skirt and I love that camel blazer! 🙂
http://www.iamalexa.biz
I love the skirt on you. Sewpetitegirl is so talented!
http://www.petitestyleonline.com
Preppy style at it's finest! Love this look, Jean!
Also, about the schoolboy blazer– I have noticed the same issue with mine, but it's less noticeable on my navy blazer. I'm just grateful that the wrinkles don't stay. I have definitely been considering a camel colored one… but my goodness, does that color ever go on sale? haha!
Wow!!! What a unique and gorgeous skirt! Love the way you styled this outfit! You look beautiful my dear!
Love this outfit! One of your better ones. How did you do your hair like that? Its got the perfect amount of swoop lol.
i love this skirt every time you wear it! and the backdrop in these pics is so beautiful!
xoxo, jenn
the stylish housewife
You have the world on your skirt! How awesome is that? Genius combination too. It's academic chic with a touch of whimsy. Love it.
-Nathy
http://earnestyle.blogspot.com/
Such a fun skirt! Love the print 🙂
You look gorgeous!
xoxo Alison
http://www.stylingmylife.com
You look amazing, I love that skirt! Your blog post is reading my mind as I'm thinking of wearing a skirt tomorrow to work for the first time! 🙂