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Transitioning your Fashion for the Seasons

As you may know I have a partnership with thredUP that involves me playing a lot of dress-up. Read all about why I partnered with the world’s largest online thrift store, here. If you hate clothing then skip this post and come back Monday for design content, but if you find yourself sitting, wondering ‘how does Emily Henderson transition her striped dress from winter to summer’ then you can check that box off your bucket list because that answer is FINALLY going to be answered (keeping in mind, I’m “transitioning” here in Los Angeles, so there’s not a heavy snow jacket in sight).

We all know that layering is key both in home and fashion, so that’s pretty much what I do here. First up – the pink shift dress – for work and play.

Emily Henderson Transitional Fashion Pink Dress

This whole experience was great for me because I rarely curate my outfits and I mostly just throw things on as soon as one of my two kids lets go of my legs, 2 minutes before I should be out the door. For this first outfit, I tucked a short and fitted chambray underneath this thick pink shift and wore my no-longer-available blue menswear duster with some booties.


Then I de-shirted, added my go-to mules (which I wear almost every day) and spring sprang.


That bag is from Fashionable, and it’s a b-corp company (meaning that they are invested in making the world a bit better) so if you are interested in that bag, I highly suggest it. It’s just so pretty. Most of the clothing is no longer available but you can troll through thredUP to see what similar pieces you can find. Meanwhile we put together a get the look (tip – the chambray shirt we chose I love but I just realized that it probably isn’t fitted enough to work underneath a dress, so make sure to get something stiff and fitted to layer).

Emily Henderson Transitional Fashion Get The Look Pink Dress


Fall/Winter: 1. Navy Duster | 2. Wave Necklace | 3. Pink Shift Dress | 4. Chambray Top | 5. Suede Booties Spring/Summer: 1. Pendant Necklace | 2. Pink Shift Dress | 3. Leather Purse | 4. Nude Mules


Below is the outfit that I would say is the biggest risk for me, and in many ways not me. I mean, I love a culotte on those fashionistas but I fear that they don’t look nearly as good on most of America as they do on models. HOWEVER I do kinda like these electric blue mom pants. The sweater is not something I would normally gravitate towards but heck, we were in a playful room so lets put on something playful, no?

Emily Henderson Transitional Fashion Floral Sweater

I do, however, love a boxy top on a fitted short/skirt or skinny jeans (and yes those are shorts, I’m not wearing THAT mini of a mini).


That is the first time in SBEH history that I’ve worn my hair up in a bun. Don’t know if I’ll rotate it into my constant ‘wavy loose hair down’ or ‘unmade hair + hat’ repretoire, but even I was like oh man, it’s nice to see her doing something different with those locks. 

Emily Henderson Transitional Fashion Get The Look Floral Sweater


Fall/Winter: 1. Rosy Lip Color | 2. Floral Sweater | 3. Navy Culotte | 4. Platform Boot Spring/Summer: 1. Blush Backpack | 2. Floral Sweater | 3. Scallop-Hem Shorts | 4. Platform Clogs

Now to a more typical ‘me’ outfit – the old striped boxy top + wide leg jean combo.


These jeans were pre-Elliot jeans, and while my post-2-baby body may not be rocking them as well as I used to, I LOVE them and feel good in them. If I could duplicate that sweater I would. I love the fit, despite the 9 stains it now has that I pretend to not notice.

Emily Henderson Transitional Fashion Jeans

Winter = sweater/closed toe, summer = blouse/open toe. It’s not rocket science but it is kinda fun to see, right?

For those of you not interested in non-design content, here! I’m holding flowers! They are for you to forgive me for a fashion post.


For those of you interested in fashion, here are some get the looks:

Emily Henderson Transitional Fashion Get The Look Bell Bottoms


Fall/Winter: 1. Striped Sweater | 2. Pendant Necklace | 3. Leather Crossbody | 4. Wide Leg Jeans | 5. Chunky Platforms Spring/Summer: 1. Blouse | 2. Pendant Necklace | 3. Wide Leg Jeans | 4. Open Toe Platforms

Lastly, and maybe my most favorite – The ‘playfully outdoorsy neutral flea market’ outfit.


Fun fact, I’ve had that Old Navy jacket since I was 23 – which was like FOUR YEARS AGO (jk) and I still wear it. This one was about the dress (which was actually a maternity dress, that I still wear) and how I wear it in winter and spring.

Emily Henderson Transitional Fashion Stripped Dress

Fall/winter = pants, boots, jacket, and hat. Spring/summer = jean jacket, colorful bag, and mules. My I’m having so much fun in that outfit! And my how very short that skirt is . . . I don’t typically rock a colorful bag, but this outfit kinda wanted it and it’s making me start to rethink my ‘only camel, nude, and black leather bag’ subconscious rule.


There you go. Again with this dress make sure that it’s thick enough to go over your jeans without doing that annoying things that jeans do underneath longer dresses.

Emily Henderson Transitional Fashion Get The Look Striped Dress


Fall/Winter: 1. Hat | 2. Trench | 3. Striped Dress | 4. Dainty Necklace | 5. Black Skinny Jeans | 6. Leather Boots Spring/Summer: 1. Striped Dress | 2. Jean Jacket | 3. Orange Crossbody | 4. Nude Mules

This post wasn’t sponsored by thredUP, although I did steal all the photos from them 🙂 So if you are looking for a VERY affordable way to hunt and find used but quality clothes, head to thredUP. Otherwise all the links here are for similar clothes as well.

There you go, folks. You get it – more layers, more warmth, closed toes, and more coverage in the fall/winter. Brighter colors, less layers, and apparently MUCH more leg in the spring/winter. Thanks to thredUP for giving me an excuse to get my model on. It was actually far more fun than I thought it was going to be.

*P.S. As you know I am very fair skinned, so I do a spray tan called the ‘Versa Spa’ on level 2 (but it’s probably different everywhere – so try before some sort of important event). It’s way better than the mystic, but so much cheaper, faster, and more natural than airbrush (at least for us pale people – they ALWAYS over do me). It takes me 4 minutes from parking to back in my car and makes me feel a little better about showing so much skin. I know a lot of you have asked about it on Instagram or in comments so I figured I’d give them some unpaid endorsement.

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7 years ago

These outfits are so cute but I really feel like someone who lives in California can’t comment on dressing for the seasons, haha. I would die of frostbite if I attempted to wear those fall/winter outfits here!

7 years ago
Reply to  Vicki

I was thinking the same thing, sitting here in my wool turtleneck! 😉

7 years ago
Reply to  Kendra

Haha! Total opposite here in Florida. Was wishing I could need layers. It gets redundant…thankfully I can live vicariously through Emily 🙂

Pam Groom
7 years ago

I can see why Emily does fashion posts. It’s fun to play dress up!

7 years ago

Ahem, I don’t usually see you in shorts and fellt compelled to say you should wear them more often. Great legs!

7 years ago

Aww, don’t apologize for fashion posts! They totally have a place in your brand. I absolutely loved all the different scenes and poses you chose for the pictures!

7 years ago

Whoaaa! Christmas morning for me. I love love love your fashion posts.
The only thing that would we it even better if you could occasionally feature different body types.
Now, going back up to devour every word

7 years ago

just wanted to pop in to say i LOVE your hair in a bun! it suits you…you should wear it up more often!

Susie Q.
7 years ago
Reply to  Abby

I second that! Your hair looks very cute in a bun.

7 years ago

I really enjoyed this post – it’s perfect for a Friday. I am loyal to this blog mostly for the design stuff, sure, but also because I love the Emily Henderson style aesthetic. I think this article helps me understand how that style translates itself into a wearable version. Two thumbs up.

My only question here is how do you wear your hair down so much with Birdie? I have a child of a similar age to her and he pulls my hair so often (and steals my glasses from my face, will grab my earrings like they’re toys, etc. etc.).

7 years ago

You look so great Emily!!! What a cute post. Great options that are interesting and not weird-bad. The shorts are super cute for you…not professional in my opinion, but absolutely adorable!
Bun hint from a frequent bun wearer: Buns look best when they are opposite your chin- draw a line from chin up your jaw and put your bun on that line 🙂 That way it sits so you can see it in front and it helps fight gravity 🙂

7 years ago
Reply to  Kimberly

How can a bun sit so you can see it?

7 years ago
Reply to  Leila

I can see mine (in the mirror, facing forward) if it’s high enough.

7 years ago
Reply to  Kimberly

Totally depends on your face shape, because this is NOT true for me. Below or above that point is wayyyy better for my bun-wearing! 🙂

7 years ago

You should DEFINITELY wear your hair up more often. Super cute on you. And those legs…….wowza.

7 years ago

She’s got legs and she knows how to
Use them! Damn girl, you look good!
I love your fashion and especially beauty posts! I feel like I can’t add one more thing to my 850sq foot rancher….but my shopping
Carts will be loaded up
Pls-once you mentioned a make up application post. Still holding my breath. 🙂

7 years ago

Fun post! I live in NYC and need about 12 more layers than this but it was still enjoyable to see 🙂
I love the brown two-tone boots you’re actually wearing in the last outfit – I wonder where they are from?

7 years ago

I love the fashion posts! They either give me a ton of ideas or they make me feel like I’m doing something right already (as I have a lot of the same pieces as you do). And thanks for the Versa Tan tip, from a fellow pale girl.

7 years ago

Loved the hair…and the shorts…on you!

7 years ago

I love the culottes and the bun on you! Adorable.

7 years ago

I love the fashion posts! Please keep doing them. I think of it like choosing a hairdresser, you pick one who looks good and can do their own hair. Designers are kind of the same way, if you look good and put together, then there’s a good chance your rooms will be the same. Designs Posts + Fashion Posts = Good Blog!

7 years ago

Girl you look like a supermodel in that floral sweater outfit. Stunning!!!

7 years ago

Emily – you are just too adorable! I love these fashion posts….keep’em coming!

7 years ago
Reply to  Lisa

Emily – I need to know! I’m so close to purchasing those Rachel Comey’s. I’ve wanted those mules for about a year now and am convinced (by you) that they are so worth it. BUT – I know I’ll wear them just as often as you do, so I need to know… do they get smelly?! Really can’t wear socks with them, and they’re not a “once in a while” shoe. They will be worn DAILY for me, just like you do. Please let me know!!!!
PS – LOVE your hair in a bun, you look amazing in this post, and as a design content lover, these posts are JUST as fun to read as all the rest.

7 years ago

You look great! Are you still doing the ‘plants only M-F’ eating thing?

7 years ago

I like the fashion posts! Especially when you photograph in your house etc. and get a little peek of design with it. I think you’ve done a good job marrying design and fashion, and for those of us who are hard core about design posts (myself included) im totally not mad at this approach for a fashion post. well done! and OMFG those rachel comey clogs are TO DIE FOR. gimmegimmegimmegimmegimmeeeeeee

Eileen Atienza
7 years ago

You are the cutest Emily! I’m sure you are told this constantly but you remind me of a way prettier Kirsten Dunst ?

7 years ago

You definitely have a specific clothing style that works for you, but girl, all those shoes are hideous. You wear heels to look taller, but the mules and the booties cut you off at the ankle. And I’ve never understood platform shoes of any kind – you’re so tiny, and they look like big weights you’re dragging around.

7 years ago
Reply to  Anna

You definitely have a specific communication style that works for you, but girl, all those judgments are hideous.

7 years ago

I just went on a SEARCH for those Rachey Comey mules for less or a similar vibe shoe and just bought these in case anyone else is doing the same:

7 years ago
Reply to  Zoe

Well done! Thank you for sharing!

Kristal Simel
7 years ago

Your legs look amazing in the shorts!!!

7 years ago

Can you provide the sources for the pink shirt (not the Gap one), and the actual maternity dress you’re wearing please?

7 years ago

Love the bun!

7 years ago

Love this!! Keep posting more fashion posts!

7 years ago

I think we all agree here that a. your legs and short shorts are best friends and b. you look wonderful with your hair up! I have the same problem in that my husband always hints that he likes my hair up better but I wear it down 99.9% of the time. Also, it’s about 20 degrees here in Chicago so this post made me even more desperate for the warm weather to get here!

7 years ago

Your fashion posts are some of my favorites! Also, I know the feeling of barely having any time to play in your own closet. I recently started setting aside 30 minutes every sunday night to go into my closet, watch a show on my ipad and plan my outfits for the week. Its fun me time and I get to get creative with what I have. Since I started doing this Jan.1, I have received so many more compliments at work. Things like “I love how you paired that” or “I never would have thought to layer those things”. What a difference it makes when you can put a little thought into what you are wearing.

7 years ago
Reply to  Hannah

Good idea!

7 years ago

Ugh I adore you. You look hot, you are rocking that bun, and you just answered the question I’ve been trying to answer for a year in LA – where the heck can I get a non-airbrush, good sunless tan?! Thank you.

7 years ago

You look AMAZING in the second outfit (floral sweater). I can see how that’s not something you’d normally gravitate toward; I wound’t either, as I love navy and black and stripes and denim. But, wow, you look incredible with a red lip, bun, and red/pink accents. I love the pants on you, too.
You have an incredible figure, so you look great in everything. Thanks for sharing.

7 years ago

Yes to the floral sweater! If I had to pick which piece of clothing is Emily the designer, not Emily the person, I would pick that one. It’s mid-century (the colors, the overpixelated design), granny-chic (the flowers), happy (the pink), and looks like the sweater version of your logo. The lips and bun make you look super current. New profile photo? 🙂

7 years ago

What shade of Glossier is that?

7 years ago
Reply to  Suzy

Good idea!

7 years ago
Reply to  S

Ops- I would like to know too. I want it!

7 years ago

You look so pretty with your hair up in a bun!! That whole outfit with shorts was so cute and fresh for you.

7 years ago

Love your big smiles here! And your hair up looks GORGEOUS, you should definitely wear it that way more often 🙂

7 years ago

You look fabulous. Loved the ones with the striped dress. The Old Navy jacket and hat look great. Keep such posts coming!

7 years ago

Loving these looks and your shoe collection!

7 years ago

Where are those ratan moose heads from?

7 years ago

I have a spray tan endorsement, too! I use the Neutrogeaspray tan, also level two. I do it at home right after the shower. You don’t have to rub it in at all, and the color is really natural. It’s super affordable and I just do it every couple of days. I live in Miami, so shorts and miniskirts are imperative throughout the summer. For special events, I also like the Sally Hansen spray on leg make up. It covers up any flaws so that you can feel really confident for a special night out.

7 years ago

Love the post!! Have to rethink my closet to transition soon (as I live in Canada I mean in like 4 months). I am on the hunt for the perfect black skinny jean. I have 4 young kids and want a jean that can be washed and dried on hot and still keep its shape and colour. Also due to my post mom bod I need something a little higher waisted. I’m also looking to spend under $100. I know it’s the holy grail here but if anyone can help a sister out:)

7 years ago

Terimakasih atas sharig ilmu dan pengetahuannya. Semoga selalu menjadi manfaat bagi semuannya. Salam sukses selalu. Amin

7 years ago

I LOVE these outfits! What brand are the two-toned ankle boots in your flea market outfit? I am adoring those!

Thanks greatly for one more worthwhile article I’ve been an enormous enthusiast to the previous few months and i really enjoy reading your posts

7 years ago

You’ve got some killer legs! You should be proud of those!