Alright! Here we go with my first ever fashion inspiration post. This idea evolved as a natural extension from both my Things I’m Loving Lately posts as well as the frequent questions I get on Instagram about what I am wearing, etc. Basically I thought it might be fun to share some outfits that I’m currently wearing often and when I mentioned this idea previously, it was well received by many readers! I’ll probably do this feature just a few times a year, likely with each season, unless you request it more often. Let me state a few things up front. First, I’m no model. As you will see my posing skills are pretty limited to standard hand on hip technique (maybe this could make a good drinking game?!) Additionally, my facial expression is frequently affected by BRF – not sure I can do much about that! But don’t focus on me – let’s just focus on the outfits. Hopefully even those outfits with items from past seasons will still provide some general style inspiration.

I decided to start with more casual attire and work toward some fancier options. Above is an outfit I would likely wear to brunch, lunch or drinks with friends. I love the way a bright silk cami can make an otherwise basic and neutral outfit pop. And, heels – in my mind, heels are always a great idea. (Handmade knit sweater from this pattern, silk cami, jeans, gray pumps, necklace.)

Surviving cold winter temps while still looking and feeling fashionable is always a challenge. This is my favorite overall look for errand running and general weekend life in the fall and winter. I was so wary of vests before but a good quilted vest is an absolute necessity for me these days. It’s all about the layers. (T-shirt, jeans, camp socks, booties, quilted vest, handmade fingerless mitts and cowl.)

I never used to be much of a hat wearer but this winter a few knitting projects have changed that! This is another casual look I like for just hanging around the house or running errands in less than perfect weather. Also, I can’t say exactly why but I’m really in love with this raglan t-shirt. If you see me on the weekend, there is a 99% chance I’m wearing it. (T-shirt, jeans, boots, vest, handmade hat.)

This was a more popular option back in fall when the temps hadn’t dropped quite so low. Now if this look makes an appearance, leggings are certainly part of the equation. In any case, this is a cute and comfy outfit that works for just about any situation! Sadness…since taking these photos (a month or more ago now!), these boots have been declared missing, and there is an excellent chance I left them at my yoga studio (but didn’t realize until weeks later when they were long gone.) I have since replaced them with Fryes and have been really loving them. (Past season shirt dress from Anthro, many many years old long metallic cardigan from J.Crew, past season boots from J.Crew, earrings.)

The one lonely photo I managed to take for this post way back in fall when there were still leaves on the trees! Just a fairly standard work outfit. Nothing particularly revolutionary about it but I always love the polished look of a nice collared and cuffed shirt paired with a sweater and pencil skirt. (Past season pencil skirt from Ann Taylor, sweater, now sold out shirt from J.Crew, past season heels from Boden.) Note about this sweater – I love the fit overall but they run really long in the body. I don’t usually require petite in tops but this one I wish I had gotten petite!

Most often I wear button down shirts as above, with a pencil skirt, but sometimes I like to mix it up and wear one untucked with a belt over the top. (Now sold out shirt from J.Crew, pants, past season belt from J.Crew, past season heels from Boden.)

This sweater is probably my favorite find from fall and I’m sad that it sold out so quickly because it was gone before I even had the chance to share it in Things I’m Loving. I wear it lots of ways – with jeans and boots for a casual look, with a midi skirt (see below), with a golden yellow pencil skirt (pictured below), but my favorite of all is paired with these pale pink pants and my fave heels. This outfit just gets me. (Sold out too fast sweater from J.Crew, pants, heels.)

I did make sure to mention this silk midi skirt in a past Things I’m Loving and I got a lot of questions about what I like to wear it with. The short answer is, almost everything! Though it is currently sold out, I fully expect it to return in the spring, hopefully in white as well as other colors. I also have one in lemon yellow and love it too! Here are a handful of my favorite looks for it. (From left to right: sold out too fast sweater and pink heels, past season plaid shirt, heels and necklace all from J.Crew, and now sold out bright lace top and past season heels from J.Crew.) Basically, I wear this skirt as often as possible without it seeming weird to the people who see me every day.

A good lace top is an absolute wardrobe staple as far as I am concerned. This top has been a long time, hard hitting favorite of mine. It can be dressed up or down, and I incorporate it into many outfits. This is one of my recent favorites. Very classic. (Past season lace top from Anthro, skirt, past season heels from J.Crew.)

This is one of those looks I adore because it is extremely comfortable while simultaneously being stylish. Win-win. Also, shouldn’t bright green be a more popular color? It is fabulous. (Past season black sheath dress from Ann Taylor, leggings, boots though mine are leather which is not currently available, past season cardigan from Banana Republic.)

Last look for now – this dress was an impulse purchase because I found a great deal on it, but I was unsure of the whole faux leather pleated skirt situation. I have to say, the moment I tried it on, this was an instant favorite! For me, the highest level of outfit success is compliments from random strangers, and every time I wear this I receive many of them! Though the dress itself is no longer available, a separate skirt is, so the look should be easily recreated with a white keyhole top. (Now sold out dress from J.Crew, boots.) Side note – due to the nature of the top, this dress requires a good quality smooth bra. This one is my fave fave fave!

I hope you enjoyed this first fashion post! I already have quite a few outfit ideas piling up for the next round, so maybe I will share a late winter/early spring edition soon.

  • Melissa Brooker

    Annie, you are incredibly photogenic! I love all of the outfits, but my fave is the pink pants, sweater and pink heels! It just looks amazing on you! I also suffer from BRF, i can definitely send the wrong message when i’m not careful! Anyways, i love this post!!

  • Some great ideas here and you look SOO pretty – I especially love the white/black dress with the pleated skirt, it suits you so well!

  • Annie

    Thank you Kerry!

  • Annie

    Thanks Melissa! You are so sweet :)

  • thatchicchick

    Love all these! I can never figure out the vest thing, but I love the look! What’s the temperature range in which you typically will wear the vest?

  • Emily P.

    Love these posts! Thank you for sharing!

  • Annie

    I wear mine basically all the time throughout the fall and winter unless it is below 30. If it is warmer (like in the 50s) I wear it with a thinner shirt underneath as shown above. If it is colder (30s) then I would more likely layer with a sweater underneath and definitely have the mitts and cowl as well.

  • Paige Cassandra Flamm

    I love that third outfit with the rain boots! It’s so cute!


  • Megan

    I love this post so very much! You are so stylish and always inspiring- love this new series on your blog!

  • Angela

    I love these. I like seeing the pieces in the Things I’m Loving posts and then seeing what you do with them. My favorite is the mustard pencil skirt with the lace top. It is lovely. You are lovely.

    (After I finished tying this, my three year-old son said, “that lady is so pretty.”) :)

  • Annie

    Aw, you are so sweet and your son’s comment made me smile. What a cutie.

  • Annie

    Thank you Megan!

  • Callie

    I love all of your outfits Annie! I only wish everything was not sold out online, but I am saving this post for inspiration! Can’t wait for the next fashion post! Also, just wondering if you have any recommendations of winter coats/jackets you are loving lately? I am on a mission to find a good one!

  • Natalie Stachon

    This post was SO MUCH FUN!! Your outfits are perfect. I absolutely love your color choices, from the mustard yellow to the bright green to the beautiful purple silk cami.

    You dress really nice for work. Like, really really nice. None of my doctors have ever been dressed as nice as you :)

    I only have one question from this post – how can you wear heels so often? And wear them to work?! I can barely wear a wedge for 30 minutes before my feet feel like they are going to die. What’s the scoop?

    P.S. Tonight’s soup = tortellini soup from the blog :)

  • Annie

    Thank you Natalie! You are so sweet. Ha, your question about the heels – not sure how to answer it! Part of it is definitely that my specialty allows me to sit the majority of the day. If I were on my feet all day long, it would probably not be feasible to wear them so often. However, there are days when I have to walk a lot to go do various procedures and I usually do fine with that. I think part of it is just being used to it because I wear them 80-90% of the time, and also making sure that they fit really well.

  • Annie

    Yes! Two great coat recs for you (probably should have included those but I took these photos weeks ago and just wanted to get the post published). Both are from J.Crew (surprise, surprise.) This coat ( I have from years ago in a bright cobalt/indigo color. I adore it! If they had the pictured yellow in my size right now, I would buy it in no time. Love this coat!

    For a more casual option, I upgraded to a white puffer coat with a faux fur lined hood this year after having the same boring black North Face for the past 15 years (no kidding). I love it! It seems like it may be sold out now because I can’t find a way to link to it but you can see a pic of it here:

  • Carolyn

    Love this post!!! Great ideas and you look great – thanks for sharing :)

  • Ruth Beaty

    Love the clothes, but most of all, thank you for that video reference! I ’bout fell of the couch laughing and I had to share with the rest of the girls in the family. Now I know what’s wrong with me. I’ve always been accused of being mean or having a “bitchy” look, and now I know the name for it!

  • Tess

    Beautiful outfits! Also, thanks for sharing the links for the handmade knits! I recently started knitting and I’m working on my first sweater right now! It’s very addictive!

  • omahacommenter1

    Such cute outfits! Thank you for sharing them and where to put them together. I’m horrible at clothes, so this is great. I espeically love the raglan – those are my favorite!!!

  • Karen

    Would you recommend those leggings you are wearing? I bought a super cheap pair at costco to see if I could get on board the legging trend and am now looking to getting better quality ones.

  • Annie

    Yes! Love my PACT leggings. Also, they are Fair Trade certified and any time I can find that I am very excited!

  • Annie

    Yay, have so much fun with it! It is truly addicting :)

  • Annie

    Right?! Now we have an explanation for it. If only this were a more widely understood phenomenon, I could just be like, “I have BRF!” and people would understand that I don’t hate them despite my face. HA!

  • Katie Wendel

    What a fun post! This must have been so much work, thanks for putting it all together! Would you mind sharing a tutorial sometime on the hairstyle pictured many times above (in the last set, for example)? The part up with like a fancy pouf situation in the back? It looks so great! Thanks!

  • Dawn

    Beautiful outfits, Annie! Thank you for sharing. I got inspiration for the work week from a couple of them. :) My favorites, however, are your outfits with the items you knitted yourself. The green hat is beautiful and looks so pretty with your eyes.

    As a suggestion, do you ever wear simple long gold necklaces (like with a natural gemstone at the end)? There are a few outfits here that I think would look fantastic with that addition.

  • Rachel Taylor

    Loved these! Can’t wait to see more in the future!

  • Lara Langeneckert

    After my old Target rain boots developed a hidden crack somewhere (resulting in freezing toes during my pedestrian commute this morning and soggy tights at work today, UGH) I am on the hunt for a new and more reliable pair. What do you think of your Hunters? I’ve heard raves from some, but others have said that they are made in China now and the quality has declined. I’d love to hear your input. Thanks!

  • Annie

    Yay! So happy to hear that :) Thanks Rachel!

  • Annie

    Mine are at least a couple of years old, so I’m not sure when or how any manufacturing changes might affect my response. All I know is that I LOVE mine and definitely recommend them.

  • Annie

    Thanks for the jewelry suggestion Dawn! I don’t wear a lot of long necklaces but do have a few from Erin McDermott that I have been eyeing. I might have to incorporate a few in the future!

  • Maria

    What do you usually wear when you are home with your kids? I’m a SAHM (who misses dressing up to got to work), and I struggle with motivating myself to look “polished” most days, especially those winter days where we are going to be in the house all day.

  • Julia

    I love how ladylike and modest your style is! Plus, it’s totally suited to chasing my kiddos around!

    I design knitting patterns and love seeing what projects you pick out!

  • Annie

    I usually wear something like one of the first three outfits when I’m hanging around at home. I generally still do my hair and makeup because I feel super grumpy when I don’t. Most likely the second or third (i.e. something with layers and hand knits) because I am always cold!

  • Alana

    Love the outfits! So much inspiration. Thanks for taking the time to to blog. I love how you have such a well-rounded life and your honesty on here. Your blog is truly my favorite!

  • Annie

    Thank you so much Alana! You are so sweet :)

  • Gail Werner

    You look beautiful in everything you wear, Annie! Having seen you in the lace-pencil skirt combo, I can attest it’s one of my faves on you! But LOVING that faux leather skirt dress! (Can I come raid your closet?!)

  • Laurel Nippert Miller

    Love the outfit inspiration. You can totally rock the pencil skirt look.

  • Meghan Jenson

    You look fabulous Annie! Thanks for sharing outfit inspiration. I liked the skirt wear you shared three different tops to it!

  • Annie

    Thank you Meghan!

  • Annie

    I have! I do a lot of hot yoga, barre, and have gotten into running. It has been working wonders!

  • Emily @ Life on Food

    These are all so cute. I need to get out of my clothes rut. Great finds here to do just that.