So I have been a civilian now for about a year. One of the oft stated challenges of those transitioning out of the military is figuring out what to wear every day. Not me! I love picking out my own clothes. Uniforms were convenient, no doubt, but were never made to fit a body shape like mine (aka girl shaped, with hips and stuff).
Assembling a civilian work wardrobe can seem spendy, and since I was going to a job as a contractor for a federal agency (meaning, potentially vulnerable to budget cuts), I wasn't willing to invest significantly. So here is what I did (over time, not all at once :-)):
1. Check out the closest outlet mall. Stores like Back and White, Chicos, Ann Taylor and Talbots are usually there. Most of the stores at the one by us give a 10-15% military discount :-) and have great sales on holiday weekends.
2. Find an awesome TJ Maxx (or similar). I am not sure if this is a fact or not, (since I have checked out a total of 2 locations) but I found the inventory varies somewhat depending on the store. The TJ Maxx in ritzy Georgetown had lots of great stuff.
3. Find good consignment/thrift stores. Really. There is a chain called Buffalo Exchange where I have found some great stuff, and we have a local thrift store that my daughter loves that occasionally has a rack of blazers and jackets that I have pounced on. A $8 wool blazer that you spend $8 to dry clean (thus removing any stranger cooties) is a way better deal than you'll find at the mall.
4. Always, always scour the sales racks. And don't overlook the BX, they carry a couple work-appropriate-but-not-old-ladyish lines that are great. I have a dress I grabbed off of the sale rack at the BX for $24 that ended up fitting perfectly, is super comfortable, and I get complimented on every time I wear it. (Was I there for a dress? Of course not.)
5. Shop in your own closet. There are quite a few things that I hadn't worn very much that now make great work clothes. I have a top I bought at Target I think in 2004 that still looks great and with black pants and a cardigan is totally work appropriate.
6. Take someone shopping with you that isn't afraid to give an opinion. My 15 year old is good in this role - and she has about a 90 minute shopping trip tolerance that suits us both. My friend Susan is also a great shopping partner - she knows her stuff! She is great at paring down a full shopping cart into an acceptable (affordable) amount.
So you all might be shopping pros with a carefully curated closet to whom all of this is obvious, but I am not. I hope this helps!