Sweatshirt: Embellished Sweatshirt ($118)

From Left, Earrings: OdlR Cabochon Clips ($90) Bag: Arrayed in the Shade Bag ($128) Shoes: Kors Snake Effect Pumps ($110) Top: Tie-Neck Top ($110) Skirt: Telegraph Pencil Skirt ($138)

From Right, Earrings: House of Harlow Sunburst Studs ($55) Sunglasses: Kors Scarlett Sunnies ($99) Bag: IIIBeCa Reede Tote ($198) Shoes: Splendid Cannes Flat ($78) Top: AE Chambray Shirt ($35) Pants: Reiss Ross Slim Jeans ($170)

Polyvore Set Here.

For Casual Monday. The trick to being able to wear a sweatshirt to work is to wear it as if it were a nice sweater.  You can’t throw it on with a pair of jeans, you need to dress it up.  To lighten and lift the sweatshirt, I chose a fitted pencil skirt in the oh-so-hot peacock teal color and a light-as-air tie-neck blouse. 

Choosing a bag and shoes for this combo was a bit of a challenge.  I wanted something that was fall appropriate and work appropriate but not heavy.  The snake-effect pumps are what I would choose for a grey wool sweater, so I used them here as well.  I also didn’t want to choose a grey bag because I thought that would be too much grey, so I decided to use this muted-blue zipper satchel to complement the teal skirt.

If you like the skirt, Apt. 9 makes a similar version that is currently on sale for $27.

How you choose to wear your hair with this outfit determines the jewelry.  I like to wear my hair up when I wear tie-neck blouses, so I chose a pair of statement earrings.  If you want to wear your hair down, I would push up the sleeves on the sweatshirt and choose a brass bracelet that matches the sequins on the shirt.

For the makeup, I would wear a soft pink cheek, a light burgundy gloss or stain like Clinique Black Honey and a charcoal grey eye palette applied with a light hand.

For a Day Trip.  Weekend day trips to the countryside around D.C. are one of my favorite autumn activities.  If you haven’t been to Charlottesville or the Greenbrier, they’re both definitely worth a visit.  Some people are into Williamsburg, but I have an aversion to reenactors, so I stay away.

This outfit pairs a chambray casual shirt with a pair of colored-denim jeans and the sequin sweatshirt.  I chose the magenta jeans because of all the colors for sale this season, I think the purples and burgundies have the most versatility.  However, if I were buying a colored pair, I would look for something in a lower price point like these eggplant Rich & Skinny’s for $90 or these plum-colored R&J Couture jeans for $39.

I love these sunburst earrings, and since this is their third (?) appearance on the blog, maybe it’s just time to buy them.  I just bought this sunglasses to replace another Michael Kors pair that I’d been wearing since 2008, and they’re really nice.  And the shoes were chosen for comfort with a hint of style, or as the salesgirl explained it to me, “They’re stylish TOMS.”

I also just bought the bag because somehow I’ve gone all this time without a casual tote.  What sold me on the bag was the rigid construction, quality materials and the fact that the liner comes out so that it can be washed or used as a drawstring bag.  So if your shoes get wet/dirty and you don’t want to put them in your purse, simply dump the contents of your bag into the purse and use the liner to haul the gross shoes.

If you’re looking for a casual tote that’s less expensive, this one has contrasting fabric and is just $42.

For the hair, I would probably wear a curled, bouncy ponytail, teased at the crown.  For the makeup, I would choose a beige eye color with just a hint of gold shimmer.  I’d also paint my nails a deep, dark purple like Essie Wicked.