How To Build A Comfortable, Stylish Winter Wardrobe For Under $500

You don't need tons of cash to be warm, comfortable and hott (with two t's) this winter. Just a few key pieces will complete your winter wardrobe needs for both workdays and weekends, because you probably already have some basics to fill in the gaps.

The secret to easy dressing without spending a ton of money is to choose a main color scheme and stick to it with everything you buy. You can do either black/grey or brown/tan tones. (This fall I got a raise so I'm branching out into brown/tan, but I normally stick to black and grey as my basic scheme.)

The 7 basic, key pieces

1) a pair of boots 
2) a pair of leggings
3) a pair of colored jeans
4) a sweatshirt hoodie
5) a few sweaters and tees
6) a scarf, and
7) a coat

Get it in your head that you don't need a closet stuffed full of clothes to dress well; in fact, the simpler the better. I promise it's way easier to get dressed when you aren't overwhelmed by too many choices, clothes that don't really fit, aren't in style anymore, are worn out or in disrepair, or that you just don't wear anymore because you don't feel great in them.

First off, treat yourself to a new pair of boots this winter. Depending upon the weather in your location, you can go with either ankle, calf, or knee high boots.
Here in the Rocky Mountains, we are boot-crazy. So yes, I own about 8 pairs total, but that is totally unnecessary.
If you are going with a black/grey color scheme, you want to choose black or grey boots. They will go with everything you wear.

Next, get your leggings and pants. For the black/grey scheme, a pair of black leggings are a must. You can also get a pair of black stretchy jeans or jeggings if your budget allows, and then I would add a pair of colored jeans in another color that pops with black, like the fuchsia jeans I show here.

Basic black/grey winter wardrobe. I show all three boot options here, but you really only need one pair.
For tops, I recommend three sweaters, with one of them being a long cardigan that you can layer over tees. Stick with greys and blacks. Then add a white tee and a black tee--these can be long or short sleeved. And finally, a fuzzy-warm-on-the-inside sweatshirt hoodie for weekends.

For accessories, I recommend getting a scarf that goes with everything, like the black-and-fuchsia leopard print one I show here. Or, a basic black/grey/white patterned scarf will work as well. You need a black belt and a black/grey bag, and you're all set.

Now Let's Make Some Black/Grey Outfits

Outfit #1 - Long sweater over leggings

Outfit #2 - Colored jeans and sweater

Outfit #3 - Black jeggings, tee, and long cardi

Outfit #4 - Colored jeans, black tee, scarf and coat

Outfit #5 - Leggings and sweatshirt

Now, I could keep going with these basic pieces, making different outfits--these are just a few of the options. You can also build on these basics with items you already have, or things you find on sale here and there and want to add in.

The Cost of the Black/Grey Wardrobe

Black calf-high Aerosoles boots: $75 on sale, bought about 3 years ago
Fuchsia scarf - Claire's boutique: under $10
Long black/grey marl sweater - Eddie Bauer outlet: $30
Grey sweater with white shirt tail - Calvin Klein outlet: $48
Long black cardigan - Target: $20 or less (don't remember)
Black leggings - JC Penney: $15 on sale
Black jeggings - Macy's I think: $20 on sale
Colorado Sweatshirt hoodie - $30
Pink Arizona skinny jeans - JC Penney: $20
White tee - JC Penney: $10
Black long sleeve tee - Target: $10
Nautica stretchy black belt - Steinmart: $10
Black Skechers tennis shoes - $40 at the outlet
Puffer coat with faux fur trim - Eddie Bauer outlet: $90
Backpack purse - Calvin Klein outlet: $66

Grand total: $494 (not bad, but you could reduce it even more by getting a less expensive bag and coat.)

And Because I Can't Stop, Here's the Whole Wardrobe Again in Brown/Tan

If you want to go with a brown/tan color scheme, obviously you want your boots to be in the brown/tan color family. I'm adding in a heather grey legging, an olive skinny jean, and a denim jacket. I couldn't get away with just one scarf with what I currently own, so I'm using a light grey as well as a warm brick red one. For tops, a leopard sleeveless sweater, a basic cream cable knit, a plum sweater dress, and a long oatmeal cardi, plus a greenish-grey tee.

Outfit #1 - Plum sweater dress over leggings

Outfit #2 - Olive skinny jeans, cream sweater, and grey scarf

 Outfit #3 - Long cardi over leggings with red scarf

Outfit #4 - Sweatshirt hoodie and leggings

Outfit #5 - Leggings, tee, scarf, and coat (except I forgot the scarf, but either the red or the grey would look great here)

The Cost of the Brown/Tan Wardrobe

Olive Arizona skinny jeans - JC Penney: $20
Grey infinity scarf - H&M: $20
Cream cable sweater - H&M: $20
Plum sweater dress - Athleta: $138 (yikes - this will put me over)
Grey heather leggings - Athleta: $80 (and this too)
Oatmeal long cardi - American Eagle: $24 at the outlet
Oklahoma sweatshirt hoodie - $45 online
Tan Baretraps calf boots - DSW: $80
Organic cotton greenish-grey tee - Whole Foods: $6 on clearance
Red infinity scarf - "Wrapables" on $12
Puffer coat with faux fur trim - Eddie Bauer outlet: $90

Grand total: $490 (and you can get way less expensive leggings and sweater dresses at places like Target and JC Penney. Also, I'm not adding in the Dooney & Bourke tote, which I got at Dillards on sale for $150 I think, this past summer. You can get similar bags for way less.)

Feel free to invent your own color scheme and to shop at the stores you love, but if you get my 7 basic, key pieces (Recap:
1) a pair of boots 
2) a pair of leggings
3) a pair of colored jeans
4) a sweatshirt hoodie
5) a few sweaters and tees
6) a scarf, and
7) a coat should have an amazing core winter wardrobe for the cold months ahead. And if you're like me, nothing helps me say "Bring on winter!" like warm, comfortable, stylish new clothes.