1. Get a great fitting pair of pants for the middle of your journey. Very few people actually enjoy trying on pants so it is tempting to just "make do" with belts and long shirts to cover ill-fitting bottoms. Don't do it. In a workplace, ill-fitting pants make you look unprofessional and in your personal life, they make you look sloppy. All you need is one pair of black work trousers and one pair of denim to get you through a transitional phase.
2. To subsist on just a few basic pieces of clothing, accessorize and pair pieces in creative ways. For example, one day you can wear a black knit sheath dress with a cardigan and a bright scarf. The next day you can wear that same dress layered over your white oxford shirt and with a belt defining your waist. Then you pair the belt, oxford, and cardigan with your black pants for work and then again on with denim for a weekend look.
3. Don't give away/throw away all your clothes the second your body shape/weight changes. Less tailored blouses and sweaters will probably still be wearable for a longer time than your pants, so make sure to try everything on before it heads for the door. Also, keep in mind that there will often be unforeseen fluctuations. So while you may be tempted to purge everything in a now-too-big side, I would suggest keeping a couple basics folded away on the top shelf of your closet.
4. Shop for lower quality pieces. This is the time to head to Old Navy and H&M instead of to Banana Republic and J. Crew. Although the pieces won't last as long, you won't feel bad about retiring them after you get to your final goal size.
5. During a transition phase you will probably be able to wear the same size for several weeks, if not months, at a time so you want to make sure that you can still put together appropriate outfits for all your professional and personal obligations. Here is my list of "the basics" that will keep you looking stylish:
-1 pair black work pants
-1 pair dark wash denim in your favorite cut
-1 black sheath dress
-1 patterned skirt
-1 button front oxford shirt
-1 cardigan in a solid (not neutral) color
-1 long sleeve tee (not black)
-1 patterned scarf
-1 neutral belt
Don't think you can look stylish with only 10 pieces in your closet? I will be posting all the outfit combos later this week!