Boots: Ciao Bella Tad Boots ($120)

From Left, Sunglasses: Michael Kors Oversized Sunnies ($99) Earrings: Pearl Studs ($50) Bag: Minkoff Mini-MAB ($495) Sweater: Club Monaco Diamond Cardigan ($160) Tights: HUE 3-Pack Tights ($39) T-Shirt: Scoop Neck Tee ($17) Skirt: Reiss Scarlet Skirt ($180)

From Right, Sunglasses: Sicily Aviators ($98) Earrings: Pyramid Studs ($18) Bag: Coach Candace Carryall ($398) Scarf: Burberry Merino Scarf ($505) Coat: Pringle of Scotland Cut Lapel Coat (sold out) Sweater: Acne Pinapple Sweater ($270) Jeans: Paige Premium Skyline Jeans ($158)

Polyvore Set Here.

I have no fear of flat boots when it comes to business attire.  I’ve even been known the wear my flat boots with my business suit if I don’t have anything critical going on that day.  But I’m lucky to be tall enough that I can do that, so if you’re a little on the short side, you might consider a heeled tall boot instead.  

Why tall boots?  They’re stylish, comfortable (if you find the right pair) and they keep my feet and calves warm and toasty all winter long.  So even if you don’t plan to wear them all day, I think flat tall boots are the perfect winter commuter shoe.

Casual Monday.  On Mondays, I want something simple and comfortable.  Because starting a new work week when the sun rises so late is hard enough without having to plan a glorious outfit.  I like this combination–pencil skirt with t-shirt and structured cardigan–because if the pieces fit you well, it looks really chic but is also pretty cozy.

If I haven’t convinced you that the black pencil skirt is the greatest thing since champagne was invented yet, then let this set add to the growing list of black pencil endorsements on this blog.  It’s a great basic that can be dresses up or dressed down and worn for nearly any occasion.  Need a cheaper one?  A friend of mine just purchased this MaxStudio wool faille skirt and loves it, and this Anne Klein pencil is a solid choice at ($60).

I added a black Rebecca Minkoff satchel, pearl studs (because the sweater has a bit of a prim quality to it) and oversized sunglasses to complete the outfit.  If you need a less expensive bag, this R & Em satchel is pretty close at $95  and if you don’t need it in black, this Halogen satchel in Taupe is even cuter (I think) at $149.

For the hair, I would wear it half up-half down with a light wave.  For the makeup, I would choose a cranberry-colored lipstick, pink blush and black eyeliner.  I’d also paint my nails a cranberry red like OPI Bogota Blackberry.

For a Winery Tour.  I don’t really drink wine, but somehow I am signed up for two vineyard tours in Virginia this fall.  So I guess either I’ll learn to love wine, or I’ll wind up the designated driver.  On second thought, given my driving skills (or lack thereof) I better start taste-testing some wines.

This outfit is like a dream.  The unstructured coat, the cozy sweater, the skinnies, boots and scarf are all to.die.for.  The waffle texture on this sweater is such a cool alternative to the traditional cable knit.  I found a similar sweater for $130 at TopShop, and another at ASOS for $68.  Similar scarves are also available at a lower price from Club Monaco ($90) and Lord & Taylor ($78).

If you’re looking for a similar coat, I came up goose egg on an exact match.  However, BCBG has two Ah-May-Zing long coats that are deeply discounted right now.  The first, the Alejandra ($159) has a similar slouchy shape to the coat above, but long.  The second, the Carlin, with a statement color and cool trench-like shape, is a coat that I have been lusting over for MONTHS, and it is discounted to $199.

As for the jeans, I tried on a pair of these Paige Premium jeans in the Skyline slim cut and loved them.  I’m just waiting for a pair to hit the sale racks somewhere before I pounce.

For the hair, I would probably try a French braid it to keep it out of my face.  For the makeup, I would wear a plum blush, lightly applied to the cheekbones with just a whisper of color on the apples.  I’d also apply a pale pink gloss, some brown eyeliner and fill in my brows for a natural but put together look.