What to wear with a T-shirt dress

Since this is a blog geared toward women of a certain age, I've had a few requests for postpartum-friendly outfits. I haven't personally been in that situation, but my weight has certainly fluctuated over the years, and I feel you. So here's one of my comfiest outfits; these pictures were taken on a Sunday—and I pretty much live in loose-fitting dresses on the weekend—but I added a few dressed-up elements, so you can wear this look to work or wherever the week takes you.

In this case, I couldn't go to Sunday Wine Church because of the fires up in Northern California, so instead I went to the next-best place, Grace Cathedral, which sits at the top of one of my favorite areas of the city, Nob Hill. This part of town is quite fancy—it houses the Fairmont, Intercontinental, and Scarlet Huntington Hotels, as well as some of the more tony high-rise apartment buildings in San Francisco—and on a clear day, it has amazing views. The park across the street also has amazing dog-watching.

This dress is from one of my favorite stores, COS, which is owned by H&M and until a few years ago only had locations in Europe (they're now in NYC and LA with more to come). COS is basically a Gen X woman's dream: the clothes are artfully draped, well tailored, generously cut, and quite affordable—most items are under $200. Expect to see a lot of pieces from them here. As for this dress, it's basically like a nightgown—it's probably one of the most comfortable things I own. (I'm wearing a medium and probably should have gone with a small, but alas.) It's also under $50!

Of course, the key to not looking like you're wearing pajamas is to throw a blazer over it. As you may have guessed, I own quite a few blazers; they make me feel instantly pulled together, and a well-cut one really does wonders for your look. This one is actually knit, like a sweatshirt, and so not only does it make me look polished, it too is incredibly comfortable. Double win!

Want to hear what else is comfortable? These boots! Now, they are an investment (I bought mine with my tax return last year), but you can wear them with literally everything—jeans, trousers, skirts, shorts—and they just completely step up your look. Also, I've gotten compliments on them from so many people, from TSA agents to my friend's retired schoolteacher mom. If you're considering buying a pair (and you should!), just note that they run a full size small. I sized down and still had room for insoles (making them extra extra comfy).

This bag isn't comfy per se, but I've had it for ages (if you look closely, you can probably see a few dangling sequins), and it's great for running errands on the weekend because you can just throw everything in it. I use it for traveling a lot too, but I'm looking for something a little bigger, with a zipper.

I work for a jewelry company and the weekends are my time to wear OPJ—other people's jewelry—so these are some of my favorite pieces. The screw cuff was a self-treat a few years ago when I got a big promotion; I call it the poor woman's Cartier Love bracelet. ;)

Back to Sunday Wine Church, I hope to be able to visit my favorite Napa and Sonoma wineries soon; it seems like most of them are reopening this week. But in the meantime, I'm channeling my dollars to the North Bay Fire Relief, as 100% of the proceeds will go to fire victims in Northern California. If you have anything to spare, I'd encourage you to donate as well—as signs spotted in Sonoma say, the love in the air is thicker than the smoke. 

OUTFIT DETAILS: COS striped dress || Topshop jersey blazer || ChloĆ© Susanna boots (in gold here) || Vanessa Bruno sequin tote || Giles & Brother Archer cuff || Miansai screw cuff  || Catbird mignon ring || La Soula rings via the Zoe Report Box of Style || Stella & Dot Luna pendant || Quay Australia Odin sunglasses 


Patti said...

That's a terrific COS dress, Cheryl! I like the brand too and own one of their solid black dresses. The boots are indeed special. Thanks for linking up, xo


Edwige said...

I love this look! The booties are so fab, and the striped dress is so perfect on you!

Edwige | http://www.hypnozglam.com

Joy @ The Cafe Scholar said...

The comfiest dresses usually don't have enough definition/structure to be flattering on me, but I love how a jacket with a little structure can give definition to the dress - comfort + style!

highlatitudestyle said...

Thanks for linking up to Top of the World Style. Great dress!

Julie said...

What a cute look! I love a comfy dress, and tee shirt dresses are the best!

Betsy Ramsey said...

I LOVE, LOVE, LOVE everything about this look! The stripes contrasting with the marled texture of the jacket and those amazing boots! Great outfit. Thanks for joining our blog hop this week.

Elizabeth | http://nattygal.com

Shelbee on the Edge said...

Cheryl, I love this look so much! I have never tried a blazer over a tee shirt dress, but I think I must! And those boots are spectacular! Such a great look, for sure. Thanks so much for sharing at my link up!


Clairejustine said...

Lovely outfit, great dress. Thanks for sharing at Creative Mondays last week. Pinned and featured this week at the blog hop :)

Unknown said...

realy girl looks so fabulous...love your stylish blazer wonderfull pictures dear have a nice day.. :)
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Ruth said...

You look amazing! i love the striped dress!


Michelle said...

Love the booties! These have been on my wishlist for a while