Wearing a denim shirt casually is pretty straight forward because that’s how we expect to wear it. Match it up with non-denim casual bottoms, add a few accessories and you’re good to go.  Flop proof.

But I like my denim shirt best when it’s matched with dressy items. That way I’m dressing the denim shirt up AND dressing the rest of the ensemble down. This is also a great way to stretch the wear of dressy pieces in your wardrobe.

So over the next couple of days I’m going to push the boundaries with some unexpected denim shirt ensembles. I enjoy the contrast that this creates. The interpretation feels new and fresh compared to the way I wore denim shirts back in the 90’s.

For this particular outfit I’ve matched a Gap denim shirt with a fancy sparkly cream skirt, casual studded belt and dressy baubles. I pop the collar and scrunch up the sleeves for extra textural interest. A black camisole picks up the black of the booties and fishnet hose. I tend to feel naked without a pop of colour, but a citron wristlet does the trick.

I wear this outfit on a normal work day, adding a coat, trench or jacket when it’s chilly outside. It might be too dressy for some, but it totally works for me. I guess it’s a smart casual outfit because of the denim element, but in my line of work I’m allowed to break the rules so it will pass for creative business casual.

It’s fun to watch styles filter down from prêt a porter collections to mainstream fashion. Remember how denim shirts started surfacing as fringe fashion 6 months ago?  Well, true to the resurgence of 90’s fashion, edgy denim shirts are popping up everywhere in all sorts of styles, weights, washes and price points. Sister to the denim shirt is the preppier, blue chambray shirt and that’s making a big comeback too.

This might not strike a chord with you immediately, but I’m making the denim shirt a “must have” for Spring. It’s versatile once you’ve got your head around how to wear the item both casually and with more dressy pieces. It also double duties as a great layering piece for Autumn.

It starts with selecting the right style for you. For some this means a regular shirt, and for others it means a tunic or empire cut style. It took me ages to find the right denim shirt because I was fussy about the details. It had to be soft and lightweight like a shirt and not feel heavy like a jacket. It also had to be in the right wash and fit just so. I didn’t fancy the more clean-cut chambray shirting styles either, feeling that they’re too preppy for my fashion persona – but again, this might be a nice option for you.

I eventually found the perfect denim shirt at the Gap (top left in the pictures above). It happens to be very similar to a Levi’s denim shirt that I wore to death in the early 90’s. I fell in love with my new shirt’s pearlized snap-buttons which, of course, are a great match with my unending assortment of pearl necklaces.

Once you’ve found the denim shirt that’s right for you, try wearing it in these easy ways:

• With black bottoms or micro check pants: Matching a denim shirt with a casual bottom in a different colour or fabrication is a no-brainer. Black jeans, Ponte knit pants or woven cigarette pants are the easiest options. Create outfit interest with items like a belt, lacy camisole, scarves and a jacket. Julie showed us how to wear this look with sass and style a few months ago.
• With white denim bottoms: For an effective fresh edge, substitute black bottoms for white jeans or a white denim skirt.
• With a dressy skirt: Adding a dressy spin to a denim shirt is my favourite way of wearing the item. The J Crew outfit (bottom left above) is a fabulous example of this concept.
• Over leggings: You’ll need a denim tunic like the Esprit style above for this look. Add boots or ballet flats and you’re set. So easy for gals on the go.

For years it’s been a fashion faux pas to wear denim on top of denim (for example, a blue denim shirt with jeans in a similar wash). Believe it or not, it’s this very faux pas that’s become all the trendy rage. (I love it when fashion reinvents itself to make old faux pas stylishly acceptable). I believe that denim on denim can work when the rest of the outfit variables are right. You’ll need to pick your denim items carefully and add in a good amount of additional textural interest to the outfit – a topic for another day. I’ll be sporting both mainstream and more daring denim shirt looks over the next few weeks so stay tuned for examples.

In some situations, wearing business casual skirts and dresses in the workplace has drawbacks. Several reasons were mentioned by readers in their comments on a recent post about business casual beyond skirts and dresses:

“A skirt says: Hey, I´m a woman!! Sometimes that´s not the message you want to send in a professional environment.”

“For me, my limited wearing of skirts/dresses is about fitting into an environmental norm. I live in an area where many men still feel that woman should not be in position of high authority — and often it feels as though wearing a skirt/dress draws attention to the fact that I am a female, which distracts them from focusing on the point I am making or the work that I am doing.”

“I struggle with looking professional in skirts/dresses. I don’t *try* to look sexy, but my curves just always do.”

“I’ve been wearing dresses more frequently lately, but I’ve also been getting unwanted attention from men more frequently as well. Maybe this is one of the reasons women sometimes feel more comfortable in pants? I feel feminine and pretty in a dress, but I do have to put up with more stares, honks, “compliments” from strange men, and so on.”

“I do agree with previous posters that skirts and dresses make you stand out more as a woman if you work in a male-dominated field (like I do, in technology.)”

“In a science world women just do not wear skirts and dresses. Ever. Anything feminine totally undermines your credibility.”

“Some girls in the office wear the trendiest skirts and dresses, but I just don’t think it’s professional.”

“Last time you brought this up, I mentioned that I work in tech, and that wearing skirts or a dress is so huge a divergence from the office wear norm that I might as well be wearing a prom gown.”

I found these comments very interesting. And I’m familiar with the territory. I dress clients who work in male dominated fields like technology, science and engineering, and who will wear skirts and dresses to work without giving it a second thought. They are completely comfortable wearing ultra feminine clothing items and standing out as a woman. But I also dress clients who feel that they won’t be taken seriously by their peers and superiors when they wear skirts and dresses. So we build a work wardrobe around dress slacks and trouser jeans instead.

As someone who has only ever worked in the dressy and creative fashion industry, I never had to think about whether I would be taken more seriously in a pair of slacks. As long as I look trendy, professional and modest, I’m free to wear what I like.

Do you think that women can be taken seriously when they wear skirts and dresses in male dominated professions? If the answer is no, to what extent do you rebel against the environmental norm and stand your feminine ground? Or is it best to stick to slacks so that you’re dressed more like your male peers.

Today is sandal day on YLF! This strappy sandal style is less trendy and more casual than the styles I posted earlier this morning, but just as fab.  If, like me, you prefer less strain on the balls of your feet when you wear heels, the two and half inch on this little darling might be the answer.

It’s no secret that I’m a Clarks fan. The British brand holds my attention because it usually offers great foot bed comfort, a sturdy sole and heel, and pretty good arch support. At times, the styles can look quite dowdy. But there are always hip and cool options within each collection, with this season being no exception.

The Country Meadow Wedge Sandal is simple, casual, versatile and delicious. Soft leather and a walkable two and a half inch wedge heel make it a practical and comfortable hot weather solution for skirts, walk shorts and dresses. I’ve seen all the colours and they are equally lovely, but the raspberry probably gets my top vote. At $90 the wedge sandal isn’t cheap, but Clarks make a long-lasting, good quality shoe and unfortunately that comes at a price. Available in sizes 5 to 12, do yourself a favor and try them on. There is no substitute for happy feet.