Happy Friday! It’s time for a little fun. Today I’m reviewing the looks I’ve styled for the blog and the outfits I’ve really worn over the past year to collect my favorites.
Unlike the other year-in-review posts I’ve shared for 2021, I won’t be ranking these in order. That would be way too hard…and could change on any given day. Instead, I’m grouping them into seasons.
It was harder this year to pick out my favorites and keep the list at a reasonable length. So I think that’s a good indicator that I’m getting a little better at styling outfits for my personal style aesthetic and for my body shape and proportions. Speaking of those things…
- my personal style aesthetic is classic with modern touches (get started discovering yours HERE)
- my body shape is an hourglass (discover yours HERE and learn to dress it HERE)
- my proportions are fairly even (discover yours HERE and learn to dress them HERE)
- I’m 5’8″
- I generally wear a size 8 or medium in most things
- I have neutral undertones (discover yours HERE)
- the neutrals in my color palette are black, grey, white and brown, but this year I added navy and camel, too (choose your color palette HERE)
- my signature colors are red, light blue and bright blue, pink and green (choose yours HERE)
Since writing our Dressed for My Day My Way series, in which I discussed how to dress your unique body, and our Building a Wardrobe that Works for You series, in which I shared how to build an interchangeable and versatile wardrobe, I’ve definitely acquired a closet of clothes that helps me create outfits better suited to me.
My Favorite Winter Outfits
This first category will include both outfits from last winter and this one. And I’m simply linking you to the original posts instead of sharing links to specific items. But you can definitely click through the outfit title or the link in the photo caption to get shopping and styling tips. Let’s get started!
Donegal Tweed Pants and Ivory Cashmere Sweater
This first outfit was one of last year’s Winter Classics outfits. I’ll be sharing similar looks in this year’s 2nd annual Winter Classics series, so stay tuned. I still have these donegal tweed pants in my closet on the ready. They make me think of the English countryside.
I also liked how I added just a hint of color with my red suede shoes. Tucking and belting worked for me here. But you could create a similar look leaving the sweater untucked or just front tucked. I also liked how I styled these same pants with a blue chambray shirt in this post.
Black Sweater and Trousers with Loafers
I took a little flack for this outfit when I styled my black sweater and trousers with loafers and white socks. But that was understandable. It’s definitely a different look for some palettes. But I stand by my suggestion of treating socks that are seen as accessories rather than undergarments. And if you’re wearing your socks as an accessory then I think they should either contrast with your outfit, adding a splash of color (or in this case light), or bookend it, coordinating with your top or something else at the top of your outfit.
Now if your socks aren’t going to show for the most part then I’d definitely suggest wearing them in the same color as your trousers or shoes. But as I scoured the Internet for tips on wearing socks with winter outfits, I discovered that the most stylish and modern outfits featured socks of contrasting colors and even patterns. So I loved wearing this outfit.
Winter Classics Outfit with Investment Pieces
Like most of my readers, I really don’t like spending an arm and a leg for most of my clothing. But I do believe in investing in a few pieces that will stay in your closet for years and years. Leather jackets ebb and flow in popularity, but they never go out of style. So I was thrilled when I found this leather Veronica Beard blazer (same jacket, different color) on sale last year and took the plunge.
But it’s not just the leather blazer that makes this outfit work for me. I also love the combination of grey and black and light wash denim. And the zip-in hoodie dickey adds a fun, modern touch, too. Tucking the sweater and adding that black belt helped create good proportions here as well.
Winter Classic Outfit with a Column of Black
Here’s a look I created by duplicating something I found on Pinterest. I do a lot of that. Do you follow me on Pinterest, by the way? I love creating a column of color under an outerwear piece, whether it’s a coat, blazer or even a cardigan or ruana.
I wore a rendition of this outfit to church last Sunday, as seen in this recent post. But I think what sets this particular outfit apart is the cap toe slingback pumps. They’re still available, by the way, and at a great price. They also come in solid black and solid sienna. They run true to size. And I wore these year round.
Adult Snow Day Outfit
I think I really wore this in December of 2020, but because it appeared on the blog in January of 2021, I’m including it. I love, love, love these photos, so that may have shaded my choice of this Adult Snow Day Outfit. But I sure did feel appropriately dressed for that day of exploring the Port Clinton, Ohio, area on a snowy day.
And maybe another reason I’m so happy with this outfit is because it’s my proof to myself that I’m learning how to dress for the climate in which I now live. After growing up in the South and spending the last 14 years in Arizona, it has taken me a while to acclimate style-wise. But with my fleece-lined pants, my waterproof booties and my packable puffer coat, I think I’m beginning to look more like the Midwesterner that I now am. Ha!
Jeans with Red Blouse and Brown Blazer
While this is the first How I Really Dressed for My Day photo I’m sharing in this post, I really did wear the outfits above, too. In fact, I should have shared that that’s one of my criteria for these favorites: I have to have worn them in real life. I wore these jeans, red ruffle front blouse and brown blazer to church on a Sunday last February.
These are actually cropped straight leg jeans in this outfit, too. But I made them work by wearing them with brown suede booties that have a high and narrow shaft that fit under the jeans legs well. I love combining red and brown, so I really like the color combination. And I’m always for a touch of animal print (here in the belt).
Black Trousers and Blazer with Grey Sleeveless Mockneck
Anytime I can wear my Veronica Beard Scuba blazer is a good day. And I liked how it paired with my black Nic+Zoe pants with this simple grey shell on this Sunday in early March.
Another technique I find myself using a lot these days is bookending. I wore my snakeskin pumps (about 10 years old) with a sleeveless mockneck shell in a similar shade of grey. I think the silver jewelry was a wise choice with the black and grey, too.
I also think this outfit is a favorite because I’ve kept the intensity level consistent throughout but I’ve added texture and changed up the shades a bit. I think it’s sophisticated and chic, but not out of touch.
Fun Pink and Red Combination for Winter
And my final favorite winter outfit is one I wore just recently. I shared this Fun Pink and Red Combination for Winter in yesterday’s Daily Outfits post and wore it on just an average day right before Christmas.
This is a great sweater and I really liked how it came together with black jeans and booties. I also liked the look of that JOY pin attached just at the base of the neckline. But of course the outfit really came together even more with the addition of my pink coat. I purchased this last year for this video, and I really have enjoyed styling outfits with it. Of course, the coat is no longer available, but I think the lesson learned is don’t be afraid to buy a coat in a bright, pretty color. They’re perfect for styling with neutrals, too.
That’s a wrap for winter. I could have chosen more, but I’m trying to keep the list tight. I love layering, so I think we’ll see that I had more winter and fall favorites than summer.
My Favorite Spring Outfits
Spring has proven to be quite challenging for me since moving to Ohio. I think I’m just now getting it into my head that spring is cool and sometimes plain out cold. In Georgia it was more temperate, and in Arizona it was always windy but warm. So adjusting to a wardrobe appropriate for a cool spring has stumped me a little. Let’s check out my favorite styles that I wore this past spring.
Sweatshirt and Cropped Chinos
I actually wore this particular outfit or slight variations several times. I love a sweatshirt with chinos or similar pants. Several YouTube viewers have recently requested that I do a video styling sweatshirts, so that’s coming.
I also liked this outfit because it featured my Birkenstock look-alikes from Kohl’s. I love the look, but the sandals eventually stopped working for me. So I’m considering investing in the “real things” this spring. We’ll see if they’re still trending.
Blue and White Shirtdress & Cardigan for Easter
I shared in my Favorite Purchases in 2021 post that this dolman sleeve shirtdress was one of my best purchases of the year. But it’s not just the dress that I love in this outfit. I also love the blue cardigan, the pretty floral earrings, my Madewell sandals and that Brighton straw bag.
I’ve discovered over the past few years that besides enjoying a classic style with a modern touch, I also love a retro vibe here and there. So anytime a silhouette returns from the past, I tend to like it. Hence, this shirtdress style continues to pique my interest. I recently ordered this long sleeve shirt dress from Ann Taylor and look forward to giving it a go.
White Trousers with Shell and Cardigan
Here’s another Sunday outfit that I wore to church. Hmm. I’m seeing a pattern here. Indeed, I do enjoy getting dressed for Sundays because I have somewhere to go and I want to look my best. I don’t necessarily “dress up” for church because our church is quite casual. But I do put in more effort on these days.
All the clothing in this outfit is from Talbots. I continue to be a Talbots girl at heart. I try to shop other places, too, because I want to share a variety of clothing here and on the YouTube channel. And because I don’t necessarily want to always look like Talbots. But their aesthetic definitely most closely corresponds to my own.
White Linen Blazer with Graphic Tee
My white linen blazer is one of my favorite garments in my spring and summer wardrobe. And I don’t think I’ve styled a single outfit with it that I don’t love.
Colorful Reversible Kimono with White Jeans & Graphic Tee
But it’s not just the white blazer I love in the outfit above. That graphic tee – another favorite purchase of the year – just worked so well for me in several outfits. I enjoy mixing prints, and I thought the floral kimono and floral graphic tee were a smart combination.
And speaking of that reversible kimono – yet another favorite purchase of the year – here’s another winner with it.
Mixing Animal Prints with a Kimono
In my opinion a piece like this Johnny Was kimono just begs to have fun. So why not mix things up a bit? I enjoyed styling this combination for the blog, but I also wore it on a date night and felt oh so pretty.
I just gave those black suede chunky heels to a dear friend who has the same size foot. I love them but just can’t keep everything I get to share here. Enjoy those heels, Leah!
Fatigue Barrel Pants & Coordinating Blazer
I didn’t include my Fatigue Barrel Pants & Coordinating Blazer in my favorite purchases list because they are rather trendy and I’m not sure whether I’ll be wearing them again this year or not. But I sure did enjoy them this spring and summer. They’re light weight and so fun to wear. And I loved how they worked with just a simple t-shirt.
I wore a black tee with them in another outfit that I like equally well. But I guess this white tee and faux Birks just looks a little more fun. And I think the Tumi backpack (a favorite accessory purchase) was a great addition to this outfit.
I did like some of the other things I wore in the spring, but, like I said, I’m still perfecting the cool weather spring looks. So here’s to a better spring in 2022!
My Summer Favorites
A few of these summer favorites were actually photographed in the late spring, but then I’m always trying to stay a little ahead of the seasons in my fashion posts and videos. I’m including them as summer favorites because that’s when I enjoyed wearing them on repeat.
Cropped Linen Pants & Linen Shirt
I definitely wore this combination or a slight variation several times through the summer. You know I love my linen! And to think that I didn’t even own any until a couple of years ago.
I really liked how this “sandy” grouping worked together. And that striped linen shirt from Chico’s ended up being my favorite linen piece. This outfit felt cool and relaxed, but also pulled together and classy.
Outerknown Jumpsuit and Sneakers
I was so surprised at how much I enjoyed wearing this green jumpsuit. But it felt comfortable and made me feel great.
This jumpsuit is definitely in my closet for the spring. I love how it paired with sneakers here. But I also wore it with sandals.
Cropped Chinos & Graphic Tee & Sweatshirt
Granted, this outfit is very similar to one in the Spring Favorites, but there are a few critical differences. And I love this fun summer outfit equally. Above I wore a solid white tee, but here I’m wearing my favorite graphic tee of the year. And I love the addition of the leopard print sandals.
Finally, I really did wear the sweatshirt that way, and it felt so fun. I think that little “thrown on” swath of color really makes this outfit.
Black Linen Pants with Graphic Tee & Ruana
Here’s another great outfit with that same graphic tee. This time I paired it with my black linen pants (love these!) and my ikat print ruana. I really enjoyed wearing this ruana so much this summer.
This outfit felt cool and summery, but also a little chic and elevated.
Black Parklet Shirt Dress and Sandals
I wore this Parklet shirt dress so many times this summer and any of them could have been favorite outfits. But I do think everything came together the best here. I love this black full dress with my sizable gold hoop earrings. Something about proportions I guess.
And those Eileen Fisher sandals (another favorite shoe purchase) look just right with this dress for a warm summer day.
Simple Tee & Cropped Jeans with Sandals
I’m learning to let good enough alone. Sometimes I can over accessorize. But I think this Simple Tee & Cropped Jeans with Sandals look is great because I just added a bit of contrasting color with my necklace but otherwise kept my jewelry very minimal and simple. And the flesh toned sandals keep the focus up above.
I really want to try to wear looks like this more this spring and summer.
Cropped chinos with Graphic Tee and Gold Sandals
I just realized something ironic. This is the third time I’ve posted an outfit with these cargo cropped chinos, and yet I didn’t include them in my Favorite Purchases of 2021 list. Even funnier, they are on the Most Popular Sellers list. So I really should have listed them in my favorites, too. I guess there’s nothing amazing about them, but they definitely were a workhorse in my spring and summer wardrobe.
And I loved how they paired with this simple graphic tee from Old Navy. I also like that I chose to add a little light to this otherwise “brown” look with my gold sandals. Fun!
Column of Soft Blue with Black Blazer
Another style hack that I’ve fallen in love with in recent years is adding a little juxtaposition to an outfit. So I love the contrast between the sharp black blazer and the black athletic sandals in this outfit.
Those pieces also bookend this column of casual, soft blue. There’s just something about topping such a casual summer outfit with a blazer. I’m a sucker for that kind of contrast and interest. But also this whole outfit is comfortable and easy to wear. That’s always a clincher for me.
Modern Summer Work Outfit
The post from which this outfit comes is one of my favorites of the year. I worked it up at home with mirror selfies, sharing lots of Modern Summer Work Outfits. Anyhow, I’m only allowing myself to choose one of them as a favorite, so I’m going with this one. I really like the combination of fawn colored pants, white tee and black belt. Add those black patent leather loafers and wowsa. Then add the black blazer and I’m all in.
To me it looks like a soft, creamy outfit punctuated with impactful elements in black. Yeah, I need to tuck this away and wear it as early as possible this spring.
Transition Into Fall with a Sweatshirt & Sandals
I’m not sure this is really a summer outfit, but I shared it in August so we’re going with it. I’m pretty sure I actually wore this outfit that evening out to eat, too. Y’all. I’m just a sucker for a great sweatshirt, jeans and cool, edgy sandals.
Add that Tumi backpack and I’m all in. I’m wearing Talbots relaxed fit jeans (similar) here, and I was so pleased with them. I still am, but I’m not wearing them much this winter. I’ll probably pull them out more for spring.
My Favorite Fall Outfits
We’re on the home stretch! These are my favorite fall outfits. Granted some of them look more like winter outfits to me. But indeed I wore or styled these in the fall months.
Green Blouse with Jeans
I’ve really had a thing for pretty blouses lately. And I especially love them paired with jeans. Once again, there’s that juxtaposition.
I also love blue and green with brown accessories. So I think that’s part of why this outfit pleases me so much.
Navy Ponte Knit Pants and Lavender Cashmere Sweater
I started adding navy to my wardrobe this year. I realize that means I now have a wardrobe with more neutrals than I normally recommend. But I’ve always loved navy and I think I’ve got enough quality essentials in black, so those bases are covered. Anyhow, I really liked how my navy pants paired with this pale lavender cashmere sweater.
I think I also liked that I had navy shoes and a navy jacket to wear with this combination. That certainly wouldn’t be necessary. But it worked out nicely.
Wool Lantern Pants & Henley Sweater
I know these wool lantern pants weren’t everyone’s favorites, but I really liked the look of them. I still do, but admittedly I haven’t worn them very much. I think I’ll hold onto them and see if they’re still trending next fall. After a little trial and error I finally learned how to style them – with a close fitting, simple top.
I really liked how this look came together, but by the time I figured out proportions – both lengthwise and fullness-wise, it was too cool for this outfit. I also thought pairing my gold loafers with the outfit was a smart move, but black flats would work nicely too.
Pink and Black Winter Outfit
I think this outfit is the only one from a sponsored post that I’m including in my favorites. When a brand sponsors a post I always get to select my own clothing. But sometimes the choices are narrow because of the focus of the sponsorship. That said, I absolutely loved putting together this black and pink look.
I really loved that splash of animal print in the tote bag, too. It’s the little things.
Classic Leather Moto Jacket Outfit
I remember I wore this outfit to eat dinner with friends from our church right after this photo shoot. Such a fun look, but suitably casual and a little hip.
Again, simplicity keeps this look modern and youthful. Leaving off the necklace was an intentional choice that paid off.
Travel Pants with Easy Turtleneck
I wore this easy-going black and camel ensemble on a rare Saturday when I managed to get out by myself and just shop for house stuff. I remember I came home empty-handed, but I had been comfortable in this outfit.
Wearing camel is still a little new to me. But I’m enjoying working with it. In the end, I think you just can’t beat black and camel. But adding a little animal print is always a good idea in my book.
Denim and Deep Purple with Black
I had this deep eggplant purple turtleneck in my wardrobe from last year. But I thought this outfit looked really fresh and youthful.
I enjoy wearing cropped jeans when the weather allows. So I thought I pulled it off pretty well with these shorter booties and the black belt. All those black accessories really give this outfit a little gravitas.
Thanksgiving Day Outfit
I have absolutely loved wearing my tweed Veronica Beard blazer, and I think the outfit I wore on Thanksgiving is my favorite. Everything came together here, from my camel cashmere sweater to my Chelsea boots to my pearl drop earrings to that amazing blazer. And I think I had a pretty good hair day that day, too!
Really, this outfit feels like the most authentic me right now, during this season. I’m really enjoying anything like this combination.
Blue Sweater and Black Jeans
Okay, so let’s bring a little color back to these favorites. I have been rekindling my love for blue this year. And this v-neck cashmere sweater helped. I love this simple combination of black and blue.
Oh, and that plaid cashmere scarf was such a nice touch to this outfit.
Green Cashmere Hoodie & Jeans
And finally, I’ve loved wearing my green hoodie sweater, too. In fact, I shared it again in yesterday’s post. But on this day in late November I topped it with my camel overcoat and red plaid scarf. This is one of my absolute favorite combinations of the year. I just love all the layers of color and texture here.
Whew! That was a doozy. If you’re still here, you deserve a medal. I’ll try to compensate by sharing lots of great outfits with you in 2022.How’s that? Thank you so much for dropping in and going through my list of favorite outfits for 2021. I learned a lot and maybe you gained a little inspiration.
Don’t forget, you can click through any of the outfit titles to get more information on those looks. Some items are still available, but of course many are not.
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Blessed for My Day
I think if we were ever to realize fully how much God loves us, we would be changed significantly. I know if I were to comprehend on an ongoing basis the depth and consistency and persistence of God’s love for me it would cause me to feel less fragile in my other relationships and more secure in who I am and what I bring to the table.
Think about how it might change your responses to the little things, your feelings about other people and your behavior in light of life’s challenges if you really were to tap into the depths of God’s love for you. What’s holding us back from this realization? Maybe we just need to take a few minutes each day to meditate on how much God loves us, how rich and full and deep His love runs.
So we have come to know and to believe the love that God has for us. ~ 1 John 4:16a
20 thoughts on “My Favorite Outfits of 2021”
This is a great fashion reflection back on 2021. You look good in everything, but my favorite outfit of yours is the black leather jacket. You look like the lead singer of a very hip rock band. I know you have had your hair shoulder length for a while now, but I want to say it looks so fresh and complementary. It gives you a very updated look. Keep on sharing your tips and tricks for fashion for women over 50. I enjoy reading your post with my morning coffee. Your upbeat personality is a great way to start a day. Happy New Year!
Hi Barbara, thanks for sharing. I appreciate the hair compliment because looking back over these photos I was kind of pulled to the shorter looks. But I do think the slightly longer hair is a little more youthful. I definitely need a trim right now!
I relate to your classic style and even though I’m 78, I’m constantly trying to improve myself. My latest challenge is my hair, both style and colour. I keep my hair coloured a medium blonde but it is hard to manage due to it being thin and fine. I would stop colouring it but white hair might be too stark, as well as not giving my hair the added body it needs. Would you have any suggestions for me?
Thanks. I do love your posts!
Nova Scotia, Canada
Hmm. I really don’t know, Judith. Hair is such a conundrum as we age, isn’t it? My hair has thinned a good bit, too. I enjoy Hair Biology products and they do have them for all types of situations: dry hair, color treated hair, thinning hair and greying hair. I’m not sure you have Target in Canada? Anyhow, here’s a link so you can see: https://shopstyle.it/l/bCEus
Hi Judith! My name is Judy and I am 76 and also have white hair that is thin and fine. I started coloring mine when I was 21 and finally stopped after having Chemo for 6 months 12 years ago. I have embraced it and decided to go with a short haircut that I only have to blow dry and use products that keep it healthy and shiny. You wouldn’t believe how many compliments I get on it. And I can wear a hat without messing my hair up when it is cold and enjoy the summer breezes. Try letting it go white. You can always start coloring it again. Good luck!
Mother Teresa said,
” When you know how much God is in love with you then you can only live your life radiating that love.”
Thank you, Kay, for encouraging us in His love!
Perfect. Thanks for sharing, Lois.
I loved almost everything you posted as your favorites for winter and fall of 2021. The only item I still do not care for and I stand by my thoughts on these, are the barrel or lantern pants. They make you look so much bigger on the bottom half than you really are. I never try to wear anything that makes me look bigger, trendy or not. But everything else was so right on. You looked great! I loved the ruana you were gifted but it went on sale and sold out. The other one you showed I did not care so much for. Maybe I will find one I like this spring or summer, or maybe they are not for me.
Have a blessed day.
The slingbacks with black toe isn’t the same as you have on in the picture? Your heel is higher?
Ahh, you’re right. They’re the same shoe with a lower heel. Here’s a link to the shoes I got, but they are out in my color pattern. They may come back in stock. They’ve restocked before: https://shopstyle.it/l/bCEsm
You might check out White Mountain sandals for a Birkenstock style dupe. I have several pairs and find them comfortable without the $$$ investment. I love all of the wider leg pants, including the barrel style…so comfortable, and a nice change from skinnies and straight leg.
Thanks Rhonda. I’ll do that.
Love this post! My favorite is the one with the sweater and pink coat! I love coats, but alas, I have a lot and should not buy more. I love purses too.
Here is a suggestion for a post- the most comfortable shoes in each category-pumps, sandals, tennis, boots…I love being stylish, but I hate uncomfortable shoes. I’ve yet to find a pair of comfortable low pumps. Just an idea. It is helpful when you mention when a shoe is especially comfortable.
I just bought a book about love and hope and look forward to reading it.
Could you send me all of the sheets to help me find the best colors, styles for me? I am 75 years old but still very interested in fashion even if my mid section is not as slender as it used to be. Thank you so much I love reading your blog!
What I’m reminded of is once again is I should have bought those canyon colored crops. The great colors go fast. If you hesitate you lose. I love you in shirt dresses. You look so, my husband would say, womanly. That was a high compliment from him?
Great post and I will save this to show my granddaughter with the “cool” dark roots, bare midriff in winter, and backpack everywhere, little pagan, there is a better way to dress.?
Your Thanksgiving Day look is my favorite!
I bought the donegal tweed pants at the end of the season for a great price. I haven’t worn them yet this year, but I see them in the near future. I love how great they looked when you paired them with the chambray shirt.
In the Winter and Fall, when you wear flats do you wear socks, or tights or hose for warmth? Same question for wearing heels. On a recent YouTube post you mentioned that you were looking for a thin quilted coat that you could layer under lighter coats. Lands End had several 3 in 1 coats with zip out quilted linings that can be worn together or separately. Enjoy your posts. Thanks.
I would agree these are the best outfits. You look beautiful in each and every one. These have given me so many ideas on how to style my clothing in new ways.
Thanks for your channel. I am so inspired.
I’m so glad you are getting a little inspiration here. Thanks so much for letting me know. ?