Dress: Factory Classic Sweater Dress ($88)

From Left, Sunglasses: Michael Kors Aviator Sunnies ($98) Bag: Coach Legacy Rambler ($348) Necklace: Kara Ross Imprint Resin Bib ($198) Shoes: APC Brown Ankle Boots ($495)

From Right, Tights: Fleece Lined Tights ($35) Shoes: Women’s Faux Leather Cowboy Boots ($17) Ring: Orient Express Ring ($65) Rings: Multi-Coin Ring Set ($20) Belt: Lauren Western Plaque Belt ($78) Bag: Zara Leather Messenger ($169) Sweater: Bench Barely Boyfriend Cardigan ($89)

Polyvore Set Here.

For Casual Friday.  Sweaterdresses are the perfect fall/winter casual Friday look.  They’re warm, they’re comfortable, they’re easy and they look semi-professional.  All good things.

If I’m wearing a brightly colored piece, I often like to find an accessory to anchor it to the rest of the neutral pieces.  This necklace is a prime example of that.  It blends purple, rust and taupe and beautifully coordinates with the toffee-colored boots and tan bag.  It’s just one accessory, but it makes the dress and the boots an outfit instead of just separate pieces.

When it necklace is 50-percent-off, as this one is, it’s easy to think of it as a good deal.  Especially when it’s this gorgeous.  But that doesn’t mean your good deal is cheap.  If you want to achieve a similar look for less, this pale purple and brass chain necklace is $22, this awesome ombre fringe necklace is $28, and if you think simpler is better, this long purple pendant necklace is $58.

These boots are adorable.  And I usually don’t love ankle boots.  If you want something similar these flat boots are under-$30 and these prettyclose high-heeled Anne Klein’s are $139.

For the hair, I would wear it down in the style of your choice.  For the makeup, I would go with dark sheer lip (Clinique Black Honey) and a brown gel eyeliner (Bobbi Brown Long Wear).

For the Train.  The reason this look says train and not plane is two-fold: 1) that belt buckle plus sweater plus rings very likely to set of the detector will make you hated in the security line and 2) I’ve been doing more train travel lately, so I have Amtrak on the brain.

Layering is critical on train trips.  It’s always chilly in the cars, and unless you want to spend a miserable four hours huddling for warmth with your seat buddy, who you may or may not have met before, layer it up.  I chose this sweater because it had a relaxed chunkiness that I liked for casual attire, and because I thought the oatmeal color would pair well with the bright purple.  If you’d like something that isn’t quite as long, this sweater would drown a shorter person, this Kate Hill sweater looks nice and in a similar price point.

I chose grey shoes and grey tights.  For those of you not familiar with my trademark-pending Two-Out-Of-Three-Legwear-Rule, click here for my thoughts on wearing tights.  But in short, if I’m wearing tights I vastly prefer to match the color of my tights with the color of my shoes.  (You can also match the color of your skirt/dress with the color of your tights, thereby achieving two matching pieces out of three.)

I chose a belt with a silver buckle to pull the grey shoes in with the brown sweater.  In this case, I would probably wear the belt under the sweater.  This is because wearing it over the top would likely be too bulky and bunchy given the sweater’s thickness.

I chose some mixed-metal rings with coin detail (which is kind of a trend right now; see these earrings and this necklace).  They also help bring in the grey legwear and the silver buckle.

For the hair, definitely wear it up with a collar this heavy, unless you have short hair.  For the makeup, choose neutral, light makeup when traveling because your skin needs to breathe.  I like Laura Mercier’s tinted foundation and a light application of cream blush (I just dot it on with my fingers).