long sleeve tee (similar)  |  jeans (similar)  |  leather jacket (similar)  |  suede heels (similar)

I love this leather jacket… so why don’t I ever wear it? I have so many pins on my Pinterest style board reminding me of how cool I’ll look if I wear a black leather jacket, yet it sits in my closet. I tried it on to see if I could figure out how to wear it. I’m liking it. The jeans are ok. They’re soft and loose fitting. And the heels are probably my favorites. (They have cute like tassels on the backs.)

long sleeve tee (similar)  |  jeans (similar)  |  suede heels (similar)

The outfit sans jacket.

floral blouse (similar)  |  pants (similar)  |  flats (similar)

I’ve had this floral top from LOFT forever. It’s a winner. The much-worn chino/jeans from the Gap are very comfy and flattering. The shoes (and, again, every blog seemed to demand I own them) never get picked. I think they look good here. I liked this outfit so much, I wore it to a speaking engagement later that night.

button down  | pants (similar) |  clogs

The white button down! Everyone says you need one. I don’t think I really do need one, let alone two. It looks rumbled here. I can’t figure it out. The clogs probably aren’t helping. I think a black heel might be better. And a trench coat over top!

short sleeve sweatshirt (similar)  |  jeans  |  ankle strap heels (similar)

I love this Joie tee but haven’t found a reason to wear it. The jeans are new and I LOVE them! I bought them on a trip to the Gap when I had the kids with me and they said, “Those look SO good on you, Mommy” so obviously I bought them. The shoes are Madewell from Poshmark. I think they’ve been waiting for these jeans. This outfit feels very “me” and I feel Très Française in it.

tee shirt  |  jeans  |  ankle strap heels (similar)

The same but with my new favorite white tee!

striped tee (similar)  |  jeans (similar)  |  jean jacket (similar)  |  sandals (similar)

I somehow switched over to summer. Or maybe spring. This is an imitation of an old outfit from Sincerely Jules. Only she wore it with nude flats and I didn’t like how mine looked on me. I do like this J. Crew/St. James t-shirt. But, these white jeans usually get passed over. I have another pair of white pants I like better. I obviously cut them too short. The sandals (Steve Madden, $5 at Famous Footwear!) are my favorite although they’re quite platform-y. And, the jean jacket… I’m supposed to love a jean jacket. This one is flattering but I think I’d wear it more if it were more oversized, you know? It’s not comfy or cozy (and that’s what I look for in a second layer).

striped tee (similar)  |  jeans (similar)  |  sandals (similar)

This is how I’d probably go — jacketless. I tried tying it around my waist and that was a definite no. Maybe this post should be titled, “Why I Don’t Wear a Jacket” or “Layering—I’m Clueless”

tee shirt  |  trousers (similar)  |  heels

Okay, the black trousers. Essential, right? I’m feeling better about them with the plain white tee and of course, these black heels from Banana Republic. Maybe I’ll actually wear them out of the house.

sweater (similar)  |  trousers (similar)  |  sneakers

This look. All. Over. Pinterest. Just add a long menswear coat and crossbody bag. How I wish I liked these sneakers. I think they’re too clunky. I don’t know. The sweater is good. Very good. A black turtleneck truly is a must-have, for me.

sweater (similar)  |  trousers (similar)  |  heels (similar)

I’m liking this much more. All black and one other color. A heel looks way better to me, makes my legs seem longer.

sweater (similar)  |  trousers (similar)  |  boots (similar)

This is good too. I stole this look from Style This Life. I call it, “Black-Black-Brown.”

That’s it! I had a lot of fun putting together outfits. And enjoyed reconnecting with and appreciating my clothes more. Every time I do this I get a little closer to knowing what I like and being okay with just being me. It’s nice.