Now that I’m done with my company’s Strategic Plan (hence the blog hiatus), it’s time for some real planning – fall wardrobe planning!

The end of summer. To some, those words bring sadness, nostalgia for long summer days, and jacket-less nights.

Not for me, I love Fall! (and that statement is unrelated to the fact that my summer actually arrives in “Fall”). I especially love the wardrobe options. Lots of opportunities to accessorize with layers. While Summer  is not over yet, stores are brimming with sweaters, boots, booties, scarves, jackets, and suede shoes.

I’ve already seen so much that I love, so I’m going to write a few posts about my “Fall Obsessions”

Fall Obsessions #1: Comfy weekend wear.

Some of you have heard my opinions about weekends spent in yoga, or other workout, gear. Well, to each his own, but it’s just as easy to throw on an oversized button down or “boyfriend sweater”, riding pants or leggings, and a pair of flat shoes (or, for some of us, “semi-flat”)…and you look so much more put together and presentable. And appropriate. Unless you are truly spending your entire day working out.

Last year, I became so obsessed with a pair of black riding pants, I ordered 3 pairs for backup. Perfect to pair them with? The “Perfect Shirt” by Madewell. Inexpensive, oversized, casual. I will wear this one to death.

I also love their other Chambray options which can be found here. Such a steal! Most are long enough to cover your butt so don’t worry about wearing them with tight pants. Madewell loves Chambray… and so do I!

Sweaters.

I love drape-y, comfy sweaters. No one can argue that these are less comfortable than a fleece (gasp! unless you’re hiking, or legitimately post workout).

A summer night in San Francisco was the perfect time to debut my new over-sized sweater from Joie. I want this in every color.

Vince: You continue to make my favorite “I’m stylish, but I’m not trying too hard” sweaters. Loving the bulky cowl neck this season. Unless this looks like a dress on me, it will be mine! Found at shopbop, and many other online stores.

And a slightly different style.

I’m a little embarrassed about how many booties I have in my closet (and more so by how many more I still want!). But they are just SO great. Cute, often comfy, don’t require socks, and super stylish. Some picks.

Kors Wayland. Casual (but good) wooden stacked heel, in 2 beautiful browns. I love the Whiskey color, pictured on the left.

More from Madewell. Both the Barnwood bootie (left, flatter heel) and the Zipcode bootie (slightly larger heel and rounded toe) are super cute.

Rag and Bone’s newest version of their Harrow Booties. LOVE. LOVE. LOVE. Thankfully, I’m not tempted because they were terribly uncomfortable on my feet (but according to reviews, very comfortable to some)

I decided to embrace the wedge bootie this year. I needed a new go-to weekend shoe and what is more practical than a wedge??? I treated myself to these Chloe wedge booties and I’m so excited to wear them! The lighter color was amazing…just not on me.

For more bootie options, you can see my old blogpost here.

Skinnies + oversized shirt/sweater + booties = stylish and comfy weekend wear. You can definitely go 100% flat on the shoes (not me!) to make it even more casual and comfortable. More Fall Obsessions to come…and in the meantime, enjoy those summer days!

With the warm temps this week, I’m getting ahead of myself thinking about summertime. One of my favorite simple pieces is the tee shirt dress. It’s literally one of the easiest things you can put on and you look SO much more put together than if you wore a tee shirt/tank top and shorts, or jeans. Also, one of the greatest things you can pack on a vacation because you can dress it up or down so easily.

However, I have seen way too many faux pas with this style so pay attention to:

The material! Thin jersey is so unflattering and shows off lines (and anything and everything else you don’t want people to see). Only super toned celebrities can get away with a really thin jersey dress (and they know better than to wear them). Make sure the material is substantial.

The shape! Anything baby doll-ish should have left your closet in junior high. If the tee shirt dress is a loose, shapeless style, belt it. Otherwise go for something with some fit, that will show you have a waist. This doesn’t mean it needs to be tight. In fact, for the warmer months, stay away from tight  – it looks like you’re trying too hard. Here is an example – looks very effortless and loose, but not too big and shapeless. This dress is Soft Joie, which makes great, wearable dresses.

What I like about the next dress: Stripes. Always great; really great in the summer. Fitted bottom (because the top is a bit drapey). Even though the top is drapey, its not so loose that you lose your shape. Ruching on bottom=flattering. Looks like a thick material. This dress would be so cute with a leather wrap bracelet

Can’t go wrong with simple black. And this one has potential to be dressed up more. James Perse. Great, flattering cut and neckline.

If you want to be a bit more covered up, try this James Perse style.

I love this simple maxi, also Soft Joie (that, and James Perse are my go-to’s when searching for tee shirt dresses). Great detailing around the hips should make this more flattering than a straight down tee.

  
Not a tee shirt dress, but same idea (plus, I just love it). DVF teamed up with denim designer Current Elliot to make this chic denim wrap dress that I know I’d have in my closet forever….if it was not sold out in my size already.

In terms of styling, keep it simple. Flip flops, flat sandals or wedges (great for night instead of heels which I would stay away from). Think about adding a more fun belt than the dress may come with, to add color, or a pattern to your outfit. Use jewelry and clutches to quickly change the look. Next time you’re packing for a vacation you won’t regret owning one of these!

The easiest way to look put together, or to hide an overindulgent weekend??? The Blazer! Wear it over a top, wear it as a top, pair with a dress; the blazer is ALWAYS in style.

Blazers are not a place to skimp, unless you’re just buying something for fun, like a bright, trendy color or style. For the perfect classic, I love Theory. They’re not cheap but they will last. And while they last, they keep looking good. They’re perfectly tailored and don’t lose their shape. Here is the Gabe B Blazer in simple black. I love the one-button look of this blazer.

Or, in this picture (a grey version of the Gabe B), you can see the pinstripe detailing when you roll the sleeves. Being able to roll the sleeves is important to me because it makes the blazer more fun, and less formal (and allows you to display a bracelet!)

Buy it at Bloomies or Nordstrom. Or, Shopbop for no tax or shipping!

If you want to feel less traditional or formal, try a cropped version like this DVF.  Dark or bright cropped jackets look great over a printed dress.

DIANE von FURSTENBERG Reiko Knit Suiting Blazer

Available here.

Or, try more of a schoolgirl look like this super cute navy Madewell, with gold buttons.

And this very similar Juicy Couture.

Club Monaco is another good source for stylish, moderately-priced Blazers.

Blazers-as-business-formal are so a decade ago! Leave it unbuttoned as a jacket, over a tee. Button up with a lacey cami underneath, or wear with a simple sheath dress. Throw on a scarf and you’re polished and ready to go!