I need help. I don't know how to dress :D

I am back to my weight before pregnancy, and I am still looking to loose more. I think 20 more pounds, or 15 before Christmas would make me very happy.

However, I have decided that I need to dress a little more mom- like, or wife-like, instead of the basic tom-boy-like. HA.
All my life, I have always dressed in jeans, and tshirts. I used to wear long baggy Ts, but now I wear more fitted Vnecks, skinny jeans, and more fitted clothing. I am trying to shop on Ebay for some decent deals, but I do not know what to shop for besides Ts. Weather here is cold, so I need warm clothes,etc. I would also like a few dresses for dates with my husband, but I dont know what would look nice. I have never worn heels or boot heels or etc, but would love to someday. I'm sick of being a tomboy, and I know my DH married me, but I want a sexy/woman side too.
Does this make sense? HELP ME!! I know there are ladies out there that can give me a few pointers.
Thanks!!

My fall look that I'm getting into is skinny jeans, boots, loose but no too baggy sweaters & blouses with a belt &/ a floral or animal print scarf. There are soooo many ideas on Pintrest if you have it? Forever 21 carries pretty much all the stuff for that type of look.

Watching because I need a more grown up look lol!

I always wear jeans and t-shirts, like ones from VS on casual days. If I wear a dress (in the winter) it's always black with black leggings and boots like this
I wear in the heels in the summer, but I don't like to in the winter. It's to icy and dangerous.
I would look for sweaters or nice tops you can pair a matching scarf with.

Skinny jeans, leggings, boots, chunky sweaters/sweater dresses, loose fitting shirts with a belt, colorful tanks/blouses under a blazer with jeans and heels. And you should really have a little black dress   I'm also getting a sexy red dress for Christmas time!

Posting a pic would help... or a description of your body type.

On a typical Fall day I wear skinny jeans, leather flat boots (brown, black, gray or cognac), a cute tank top, and an open front cardigan or loose sweater.
I wear my diamond studs everyday, as well as my wedding ring, and a simple monogram necklace, and then I switch up bangles, a watch, and a longer necklace usually.

Some things to skimp on (budget wise):
Everyday jeans.
Tees/ tanks and cardigans/ sweaters.
Scarves.
Trendy flats.
Cute costume necklaces/ bangles/ etc.

Some things to splurge on:
A few pairs of nice jeans. A-pockets are my personal favorites.
Leather boots in basic styles and colors - they are comfy, they will last, and the look of real leather is timeless.
A nice coat.
A good black blazer.
A good pair of diamond studs.
A little black dress.
Underwear. Seriously some seamless panties and good bras will compliment your entire wardrobe!

Quoting CerealMakerWife♥:" I always wear jeans and t-shirts, like ones from VS on casual days. If I wear a dress (in the winter) ... [snip!] ... like to in the winter. It's to icy and dangerous. I would look for sweaters or nice tops you can pair a matching scarf with."

I do like boots like those. I dont own any but think because I live in Alaska I need a nice "warm" look  
Basically I wear jeans and ugly shoes or boots, and it is nothing cute. I agree it is dangerous on the ice. Even with shoes, here you have to wear ice cleats during parts of the yr.  

Quoting Olive ♥:" Skinny jeans, leggings, boots, chunky sweaters/sweater dresses, loose fitting shirts with a belt, colorful ... [snip!] ... with jeans and heels. And you should really have a little black dress   I'm also getting a sexy red dress for Christmas time!"

What are leggings? LOL... Are they like tights? I think I know what they are but I dont want to assume something.
I agree, a black and red dress should be a must. I cant find anything I like though. It is because I have NEVER in my life owned one. Sad. I'm 34 yrs old.

Quoting nutmeg.:" Posting a pic would help... or a description of your body type. On a typical Fall day I wear skinny ... [snip!] ... well as my wedding ring, and a simple monogram necklace, and then I switch up bangles, a watch, and a longer necklace usually."

I'm looking for something. Im an odd shape. I have that getto booty, but a skinny top, bust is not large, but I do have a toned chest, and back if that makes sense. I'll add a pic to the Op soon, thanks for the suggestions!!

Quoting nutmeg.:" Some things to skimp on (budget wise): Everyday jeans. Tees/ tanks and cardigans/ sweaters. Scarves. ... [snip!] ... studs. A little black dress. Underwear. Seriously some seamless panties and good bras will compliment your entire wardrobe!"

I never thought about this before. I dont spend much time on those items and I just buy in bulk or on sale. I dont even know what type of bras to wear. I have some pushups but I am still BF right now and they tend to hurt. I normally wore sports bras ... Im so ashamed of myself. HAHA

Quoting *-PoisonIvysMama-*:" I never thought about this before. I dont spend much time on those items and I just buy in bulk or ... [snip!] ... some pushups but I am still BF right now and they tend to hurt. I normally wore sports bras ... Im so ashamed of myself. HAHA"

I feel you. For some reason, I always feel guilty buying nice undies/ bras... I guess because they don't feel as "essential" as other clothing items. But what's the point in a cute top if you can see every line of your bra and little rolls of skin right through it, you know?

I added a pic of Dh and I.

Quoting nutmeg.:" I feel you. For some reason, I always feel guilty buying nice undies/ bras... I guess because they don't ... [snip!] ... But what's the point in a cute top if you can see every line of your bra and little rolls of skin right through it, you know?"

This is true! I have tried on some tops and just hated how my bra showed through. Sometimes I want a strap-less bra, or something because the tops are cute, but the bra makes me look trashy.
Does that make sense?
The same thing applies to underwear, which can show through when you have a nice pair of tight jeans or a fitted dress.