Transitional Fall Style For Simple Dressers


Fall in Toronto this year has been quite unexpected. Here I was hoping for a cold breeze every morning when I leave the house and so far it's still been in the mid 20s for the majority of the week. I am not a fan of the warm weather so now that it's finally cooling down I can start thinking about my fall wardrobe and the outfits I plan to wear during this transition. 

As I've mentioned countless times on my blog, I am a woman of simple taste, so I will always opt for something I can easily throw on and run out of the door instead of some elaborate outfit that'll leave me feeling insecure and uncomfortable throughout the day. Since I've mentioned outfits that include jeans a lot thus far, I thought I could incorporate some dresses into my wardrobe and discuss them for today's post.

TOBI was kind enough to send me some beautiful dresses from their site as part of a collaboration and I couldn't be happier with them. It was fun to style some new pieces instead of re-styling all my old ones over and over again. I also needed some new dresses to add to my wardrobe as I had a major clean out before the summer and was only left with a few. 

T-Shirt & Dress Combo


The first outfit I am excited to wear while it's still a bit warm enough to expose my legs is this spaghetti strap dress and t-shirt combo. The t-shirt was one I picked up from the Gap this past summer and it's the perfect pinstripe to go with the wine colour of the TOBI dress. Seeing as this dress is a bit too low on me (because I'm short), I opted to save showing my skin for a more sultry look and make it a bit more casual by adding the t-shirt.

This is more of an every day look, but without the t-shirt it can easily be dressed up. I'd even do a long sleeve stripe shirt if it's a bit too cold. For a night out, I would throw on my H&M faux leather jacket, just to give it a bit of an edge and not have it look to feminine. I like my outfits to have almost a boysih look to them, and the leather jacket is perfect for achieving this. Raiding your boyfriend's closet, as I often do, is also a good tactic. 

For this look I would do a simple winged liner with my NYX liquid liner pen and leave the lips bare as I don't want the colour to clash or overpower the beautiful colour of the dress. Of course, this is also paired with the rest of my minimalist makeup routine

The Oversized Sweater Dress


When TOBI emailed me for this collaboration and let me pick out a few dresses, this was the first one I saw and wanted. I'm all about oversized sweaters, so to have an oversized sweater dress is the best of both worlds. Again, because I am short, it was a bit too long on me, but that's something I can easily fix seeing as I love playing around with my clothes and adjusting hemlines. One feature I love are the wide sleeves; they are very trendy now and fit well with the chunkiness of the dress. 

This outfit would be finished off with my high heeled H&M booties and an up-do for that casual, yet edgy look. I'd probably also throw on a pair of tights for when it gets a bit colder and to add to that autumnal vibe. I could also see myself wearing my glasses with this dress just to complete the tumblr-esque look I often try to evoke. 


A Simple Shift Dress


I've already decided that I'm going to be wearing this shift dress to my boyfriend's office Christmas party. It's a beautiful emerald green colour (that I think really suits me) and a flattering fit on my somewhat curvy figure. I'll probably be wrapping my boyfriend's brown leather GAP belt around my waist, just to accentuate the silhouette and again, give it a bit of a boyish look. My thought process has always been, when in doubt if an item looks good on you, throw on a belt and see how you feel after. I find that belts always add the final touches to any outfit. 

I'd probably also wear my H&M boots with this one as well as a pair of black leggings to stay warm on winter nights. My initial thought was to wear a red lip, but then thought better of it and my tacky ways. Instead, Lolita II by Kat Von D is the perfect shade to add some dimension without clashing with the dress colour. 

What are you transitional fall outfit pieces and how do you style them?