Dress: H&M Jersey Dress ($25)

From Left, Earrings: Marc Jacobs Octi Bolt Stud ($45) Tights: Donna Karan Super Opaque Tights ($15) Bag: Ralph Lauren Newbury Satchel ($268) Jacket: Mango Belt Jacquard Jacket ($130) Boots: Nine West Getta Boots ($120)

From Right, Earrings: Fossil Orange Studs ($20) Bag: BR Parkside Satchel ($220) Shoes: Ann Taylor Perfect Leather Pumps ($128) Scarf: Sole Society Exotic Stripe Scarf ($25) Jacket: Mango Crepe Blazer ($80)

For February.  It’s so chilly right now, I find myself reaching for a jacket or blazer nearly every time I have a meeting.  This is odd for me because I usually wear my sleeved dresses without a blazer or sweater on top.  So this look takes a short-sleeved dress with a defined waist and adds a tweed jacket with a defined and belted waist to top it.

Like the look of a belted blazer?  It can be tough to find jackets that are suitable for belting, because it works best when they don’t have buttons.  This grey open blazer from Shoptiques would look good belted, as would this square neck Anne Klein blazer.  Plus-size?  Try this Nipon Boutique blazer with scalloped edges.

To complement the hints of blue in the tweed of the jacket, I chose a navy satchel.  This Newbury satchel is a sleek work bag with separated pockets and a shoulder strap.  It’s a great style.  If you’re looking for a chic navy satchel under-$100, try this City Satchel from Zara.

I chose these boots because a sleek high-heeled boot will keep your calves warm on cold days.  I think they can be professional as long as you keep the heel under-3.5″.  If you have a bit of money to spend, I cannot recommend the Loeffler Randall Viola boot enough.  My only complaint is that they’re pull-ons, but with a ball-of-foot insole, I can walk in them for hours.

For the makeup, I would wear a subtle cheek color (rose or plum is usually best) and choose a bolder lip (red, raspberry or burgundy would all work).  For the hair, if you want to wear it up, keep the updo low and loose.  If it’s too tight, you’ll look severe.  If you wear it down, choose a style with some curl or movement to lighten the look.

For Mid-March.  When I buy a new piece of clothing, I like to know how I’m going to wear it tomorrow and weeks from now.  This dress is winter perfection with tweed, but add a softer white crepe for a look that’s perfect for the winter-spring transition.

This inexpensive crepe blazer from Mango is a great choice, but if you have a bit more to spend, try this blazer from Theyskens’ Theory.  I also like this more relaxed Helmut Lang jacket.  Plus-size?  Jones New York makes a basic white blazer.

If I wear a scarf that has a colored pattern, I like to find a piece of jewelry to coordinate with it.  The interplay between the two pieces pulls the outfit together.  For this look, I chose a scarf with an orange print and a pair of orange studs.  If orange isn’t for you, try this black and white scarf with a green accent and this beautiful stack of Carnet de Mode rings with green stones.

I chose black and white for the purse.  This combination lightens a bag up for summer, but could be worn in any season.  If you’d like something less expensive, have a look at this structured Steve Madden Btalia satchel for $88.

I’ve talked about the Ann Taylor Perfect Pumps before, but if you’re looking for a very comfortable shoe at a good price, this is a great candidate.  I prefer the lower heel myself, but this 3.25″ heel is also a good choice.

For the hair, I would wear it up in a twisted bun.  I like my hair up when I wear a scarf.  For the makeup, I would wear a black eyeliner with a pop of color on the cheeks to combat the starkness of the white.  When I’m looking for a pop of color, I head for Bobbi Brown blush in pale pink or nectar, but any brightly hued blush will do.