Happy hump day, friends! Instead of What I Wore Lately, I’ve rounded up my favorite outfits from 2021. You might want to grab another cup of coffee and take a seat because it’s a doozy!

When I first did this post back in 2019, I found 20 favorite outfits, and last year I came up with 25. I tried to stick to 25 again this year, but even after eliminating a bunch, I still ended up with “30”… and that’s using quite a bit of liberty in my counting method. You’ll see what I mean…

I guess the fact that I have more favorite outfits every year shows that I’m getting better at dressing to flatter my body and convey my personal style. It was definitely interesting to see how some of the same outfit formulas and wardrobe combinations popped up again and again. While that may seem boring or redundant, I like how it demonstrates the concept of cost per wear.

Of course, a lot of these items are low inventory or sold out at this point, but I went ahead and linked everything I could find, in case anyone wants to hunt them down on eBay or Poshmark.

My 25 Favorite Outfits from 2021

SIZING NOTES: I’m 5’5″ with an hourglass shape, and I usually take a 6/28 in pants/jeans, a small in tops, and size 8 shoe. I linked the sizes I’m wearing beneath the pictures. 

#1. This denim and boot pairing is one of my winter favorites, and I love how the burgundy leather moto over the light grey cashmere sweater levels it up for an edgy-chic date night look.

AllSaints leather moto (8; similar) // Reformation sweater (M) // similar Good American jeans (6) // Vince boots (8; similar) // belt (M) // Yurman hoops

#2. And this is as basic as it gets, but I love this monochromatic look from last January. The donegal pattern in the knit, the shape of the v-neck, and the details in the sweater are so luxe and pretty. And I think the way the sweater contrasts with the washed black jeans and the overall proportions of the outfit are really pleasing to the eye.

Vince sweater (S) // similar Good American jeans (6) // Vince boots (8; similar) // Yurman hoops

I actually wore a similar version of this yesterday, with different black jeans and different black lug sole boots. I threw a faux leather puffer vest on top for added interest and an extra layer of warmth.

Vince sweater (S) // faux leather vest (S) // Good American Good Waist Crop (6) // Blondo Dagger boots (8.5)

And here’s that same outfit, but with blue jeans.

Vince sweater (S) // faux leather vest (S) // AG Mari slim straight jeans (28) // Blondo Dagger boots (8.5) // similar 11mm pearl earrings // Yurman bracelet

#3. This is another casually understated winter look comprised of basic wardrobe pieces, but something about it is really appealing. I love the color of this sweater and the way it complements the mid-wash blue jeans. It does have a bit of that neck brace look going on, but otherwise the fit is really good. I think I need to wear belts more; I really like that extra point of interest.

360 cashmere turtleneck // AG Mari slim straight jeans (28) // Marc Fisher boots (8) // belt (M) // Lagos earrings

I also included the look with my grey cocoon coat on top. I think I wore this to go shopping one day last winter.

360 cashmere turtleneck // AG Mari slim straight jeans (28) // Marc Fisher boots (8) // belt (M) // J.Crew cocoon coat // Lagos earrings

#4. And this is another look with those AG Mari straight ankle jeans and black boots. I really like this color combination with the camel sweater, blue jeans, black vest, and black boots. And again, fit and proportion is key to keeping this simple look put-together.

camel turtleneck (S) // similar vest // AG Mari slim straight jeans (28) // Vince boots (8; similar) // Everlane studio bag // Gucci sunnies (similar for less) // Madewell necklace // Kendra Scott hoops

#5. I styled this outfit for the blog late last winter. It was inspired by some of the street style looks I was perusing on Pinterest. I love the juxtaposition of the black wool car coat paired with jeans and sneakers; and wearing a coat and top in the same color is something I don’t do very often, but I really like it.

similar black sweater // wool coat (4) // AG jeans (28) // Veja sneakers (39) // Everlane scarf // Everlane Studio Bag // Gucci sunnies (similar for less) // similar 11mm pearl earrings

#6. Moving into spring looks, I wore this outfit to church back in March. I really like the fresh color palette, the neckline of this sweater, and the combination of white jeans and light grey suede boots.

BR sweater (S) // Paige jeans (28) // Marc Fisher booties (8) // Yurman hoops & bracelet

I topped it all off with a grey trench. Unfortunately, I’m not finding anything remotely similar to link.

#7. This is an outfit I styled for the blog and then wore quite a few times over the course of the spring, summer, and fall. I’ve worn it to church, for a dinner date with Paul, and even to a viewing for a friend.

BR dolman top (S) // black Mother Insiders (28)// quilted slides (8) // J.Crew blazer (6) // chain toggle necklace // hoop earrings // snake wrap bracelet // Michael Kors crossbody

I subbed pants for the jeans for the viewing and wore a slightly more conservative sandal.

BR dolman top (S) // similar pants (M) // sandals (8) // Kendra Scott hoops // coin layer necklace // Yurman bracelet // similar shoulder bag

#8. I love the idea of a sweatshirt dress as an alternative to a t-shirt and jeans for my casual life, and there’s something about this pink tie dye print and the white leather sneakers and denim jacket that is really pleasing to the eye.

Old Navy dress // Frye sneakers // denim jacket (similar option) // teardrop earrings // Yurman bracelet // Hobo crossbody (old)

#9. I wore an iteration of this outfit several times last spring. I love the combination of the olive bomber jacket, cheetah print tee, and washed black denim. I wore this with loafers a few times, but I like it best with the fashion sneakers.

Marrakech bomber jacket // Z Supply leopard tee // AGOLDE Toni (28) // P448 sneakers (39) // layer necklace // Kendra Scott hoops // rag & bone sunnies

Here it is dressed up with black skinnies and studded mocs for a casual date night look last May. I really wish this bomber hadn’t sold out so fast; it’s so good.

Marrakech bomber jacket (S) // Z Supply leopard tee (S) // similar Good American jeans (6) // AGL studded mocs (8) // Kendra Scott earrings & necklace

#10. I bought this cheetah print utility jacket back in March of 2020, but then, Covid. I only got to wear it once or twice that season, but I did get more wear out of this past year. I love how it pairs with a white tee with light wash denim.

Rails Collins military jacket (S) // ATM tee (M) // AGOLDE Toni straight ankle jeans (28) // Dolce Vita sandals (8) // Kendra Scott earrings // Lagos bracelets

#11. This is a tried and true look that I’ve worn for years, but I had to include it because I still love it. You can’t go wrong with olive, white, and denim.

ATM tee (M) // Paige Mayslie joggers (27; similar for less) // denim jacket (S) // TB sandals (8) // Lagos earrings // Yurman bracelet

Or olive, grey, and denim…

twist detail tee (S) // Paige Mayslie joggers (27; similar for less) // Dolce Vita sandals (8) // denim jacket (S; similar option) // Kendra Scott hoops // Gorjana coin necklace // similar tote

Or just olive and grey…

AllSaints tee (S) / Paige Mayslie joggers (27; similar for less) // TB sandals (8) // Madewell earrings // Clare V. tote // Victoria Emerson wrap bracelet

Or olive and black… I think I just love these pants. And that bag really adds an extra oomph, especially when I’m not wearing a jacket.

linen dolman tee (S) // Paige Mayslie joggers (27; similar for less) // Frame sandals (8) // Madewell earrings // Clare V. tote

And here’s another variation on the theme… olive, white, and black. I still have this jacket, and I’m not sure why I didn’t wear it more. I guess it was too warm for it during the summer, but it would have been nice for fall.

KUT from the Kloth utility jacket // ATM tee (M) // utility joggers // P448 sneakers (39) // R Minkoff bag // Kendra Scott earrings // Lucky Brand bracelet // Gucci sunnies (similar for less)

#12. I also love the olive and black combo in this shorts outfit. The straw hat and tote contrast with the olive and black and keep the look summery.

linen dolman tee (S) // cargo shorts (6) // slide sandals // color block tote // straw hat (30% off with BYE2021) // Victoria Emerson necklace & bracelet // Kendra Scott hoops // Gucci sunnies (similar for less)

13. Okay, let’s move away from the olive and black. How about grey and black? I love this Sundry Saturday Skirt so much I got it in both stripe and camo prints. It’s a nice alternative to shorts in the summertime.

Michael Stars muscle tank (S) // Sundry Saturday skirt (2) // P448 sneakers (39) // initial pendant // bracelets // Gucci sunnies (similar for less)

Michael Stars boatneck tank (S) // Sundry Saturday skirt (2) // Sam Edelman flip flops (8) // R Minkoff Megan tote // Lagos earrings & Lagos bracelets

Michael Stars muscle tank (S) // Sundry Saturday Skirt (2) // Dolce Vita slides (8) // hammered metal earrings // snake wrap bracelet

#14. There are so many versions of this outfit in my archives from last spring and summer, and I was drawn to them every time. It’s such a great update to the tried and true girl-next-door jeans and t-shirt outfit.

twist detail tee (S) // Mother Insiders (28) // SE puffy slides (also at Nordstrom) // similar pendant // Yurman hoops & bracelet

ATM tee (M) // Mother Insiders (28) // Dolce Vita sandals (8) // Hobo crossbody (old) // Gucci sunnies (similar for less) // Lagos earrings & Lagos bracelets

Splendid tee (6-8) // Mother Insiders (28) // Birks // similar 11mm pearl earrings

15. I love this tie dye muscle tank with white denim. I have a thing for tie dye, and the quality of this one keeps the trendy style of the muscle tee and tie dye combo age-appropriate.

I don’t use the words “age appropriate” carelessly here; I generally don’t like that term because I think most style choices are more about personal style than age, but the older we get, the more quality matters. Good quality (and proper fit) is what keeps us looking polished and put-together, especially when wearing trends.

tie dye muscle tank (S) // white Mother Insiders (28) // Sam Edelman flip flops // Madewell earrings // Yurman bracelet // R Minkoff bag // Gucci sunnies (similar for less)

I also did this look with shorts a few times.

tie dye muscle tank (S) // Wit & Wisdom shorts (6) // Sam Edelman flip flops

16. And denim, grey, and white is one of my all-time favorite summer outfit formulas. The white crop flares with the raw step hem keep this look modern.

twist detail tee (S) // denim jacket (S; similar option) // white Mother Insiders (28) // Sam Edelman slides (8) // Lagos earrings & Lagos bracelets

#17. This is a dress I picked up during the 202o #NSale… or maybe it was 2019? I wear it a lot that summertime. I wish they would bring it back, or do something similar, but I haven’t found much. The quality is really fantastic, which is what makes this simple style so flattering.

Eileen Fisher dress (XS) // denim jacket (S; similar option) // TB Miller sandals // Victoria Emerson earrings // Victoria Emerson necklace // Monica Vinader bracelet

I also wore it to C’s high school graduation. This time I dressed it up with metallic wedge sandals and a pewter ruched clutch.

Eileen Fisher dress (XS) // Stuart Weitzman sandals (7.5) // R Minkoff ruched clutch // Kendra Scott earrings // Victoria Emerson boho cuff

#18. This tie dye tank was another summer favorite from Evereve; I wore it about once a week with cropped jeans or jean shorts. My favorite pairing is with these Mother Insiders. The casual, slightly boho vibe from the tie dye tank is perfect with the ripped up crop flares. I feel like I might be outgrowing this look… but I’m not ready to part with it just yet. I just choose carefully where I wear it.

tie dye tank (S) // Mother Insiders (28) // Sam Edelman slides (8) // Kendra Scott hoops // Lagos bracelets

#19. I grabbed this yellow denim jacket at Zappos and I wore it with several neutral outfit combos…. a grey tee and white jeans.

twist detail tee (S) // white Mother Insiders (28) // KUT from the Kloth denim jacket (S) // Dolce Vita sandals (8) // Kendra Scott hoops // coin layer necklace // Lagos bracelets

And a white tee with blue jeans. I like them both equally. This is the perfect elevated casual summer outfit. I hope they bring back this yellow jacket next spring!

KUT from the Kloth denim jacket (S) // Mother Insiders (28) // Dolce Vita sandals (8) // Gorjana star necklace // rattan earrings // Lagos bracelets

#20. Joggers became a regular part of my wardrobe in 2020, and I continued to enjoy them throughout 2021. They’re especially nice for road trips. Vuori is my favorite, but Zella makes a good pair as well. My favorite way to wear them is with a grey or white t-shirt and a denim jacket.

Vuori joggers (M) // Splendid tee (6-8) // denim jacket (S; similar option) // Veja sneakers (39) // Gucci sunnies (similar for less) // Everlane studio bag // similar 11mm pearl earrings

#21. This entire outfit is from the #NSale this year. I absolutely adore this sweater; it has such a great drape, and the color is gorgeous. And I couldn’t resist picking up another pair of Mother Insiders when they were on sale. This light wash is a nice alternative to the darker pair I wear so much, but definitely size up one, if ordering.

Vince sweater (S) // Mother Insiders (size 29) // Vince Camuto Welland booties (8.5) // Gucci sunnies (similar for less) // AllSaints shoulder bag

I wore this sweater and denim combo several times last summer and fall. This is how I wore it to meet a friend for lunch late last summer.

Vince sweater (S) // Mother Insiders (size 29) // Dolce Vita Izabel slides (8) // AllSaints shoulder bag // Madewell link earrings // Victoria Emerson bracelet

And then I wore them again with taupe mules to host family for Thanksgiving Day. I’ve worn it a few other times as well.

Vince short sleeve wool blend sweater (S) // Mother Insiders (29) // ruched flats (8) // Yurman hoops // Victoria Emerson bracelet

#22. I wore this grey short sleeve sweatshirt and light wash denim combo about once a week last fall. Both pieces have that perfect casual-chic vibe that works so well with fashion sneakers.

CHASER sweatshirt tee (S) // AGOLDE Toni straight ankle jeans (28) // P448 sneakers (39) // Lagos earrings & Lagos bracelets

#23. This is such a modern classic look; I love the washed black cropped denim with the white slub cotton tee, and the espadrilles give it the perfect luxe/casual vibe. These jeans were a new addition to my wardrobe this fall, and they’ve come in very handy!

ATM tee (M) // Frame jeans (28) // similar espadrilles // Kendra Scott earrings // similar Madewell layer necklace // Victoria Emerson bracelet // AllSaints backpack

Here’s the same look with a cheetah print tee and coated denim jacket. I wore this to travel to and from Minnesota last fall.

coated denim jacket (S) // similar tee // Frame jeans (28) // similar espadrilles // Lagos earrings & Lagos bracelets // similar tote

#24. And this is definitely one of my favorite outfits all year… this neutral plaid coat with an ivory sweater and grey jeans.

BB Dakota plaid coat (S) // Vince sweater (S) // Madewell jeans (28) // Dolce Vita mules (7.5) // Gucci sunnies (similar for less) // Victoria Emerson bracelet // Victoria Emerson necklace // Kendra Scott hoops

Here it is with a rust colored sweater. I’ve worn both outfits several times this fall and winter.

BB Dakota plaid coat (S) // Treasure & Bond sweater (S) // Mother Hustlers (28; also at Shopbop) // Dolce Vita mules (7.5) // Kendra Scott earrings // coin layer necklace

#25. And this is an outfit I styled for the blog that I really like. The cognac leather moto with ivory sweater, light wash jeans, and fashion sneakers is such a great mix of styles. I also love how the belt ties it all together. I really need to wear belts more!

cognac leather jacket // Vince sweater (S) // AGOLDE Toni straight ankle jeans (28) // P448 sneakers (39) // similar belt (mine in black) // Gucci sunnies (similar for less) // Kendra Scott hoops

#26. I love a sweater hoodie in the fall and winter. This one was another #NSale purchase this year, and I’ve worn it a lot with these light wash jeans and P448s.

cashmere hoodie (similar) // AGOLDE Toni straight ankle jeans (28) // P448 sneakers (39) // earrings // Madewell earrings

I also like it paired with off-back jeans and taupe mules.

Nordstrom Signature hoodie (S) // similar Good American jeans (6) // similar mules

#27. This is a similar color combo that I’ve worn a few times. I really like the oatmeal sweater, taupe moto, and off black denim, and the way the taupe suede mules bookend the look.

BlankNYC moto (M; similar) // Vince sweater (S) // Mother Hustlers (28; also at Shopbop) // Dolce Vita mules (7.5) // similar 11mm pearl earrings

I also did this with light wash jeans and lighter beige boots. This time the boots and sweater are a similar shade.

BlankNYC moto (M; similar) // Vince sweater (S) // Mother Insiders (29) // Vince Camuto Ackella Bootie (8)

#28. I like this Naadam boatneck sweater so much I have it in two colors — Merlot and Mink. As much as I love the Merlot and have probably worn it more than the Mink, I chose this outfit to include in this post because I love the way I styled it with the off-back skinnies, suede stretch booties, and the faux leather puffer jacket for a holiday date night look.

A+F Vegan Leather Mini Puffer (S) // Naadam cashmere boatneck in Mink (S) // similar Good American jeans (6) // Aquatalia boots (8) // Kendra Scott earrings // R Minkoff ruched clutch

#29. I don’t wear a lot of dresses, but I love a good sweater dress, and I actually found TWO this year. That’s kind of a record. The first is this cable knit mock neck from LOFT. I’ve worn this outfit several times during the holiday season… this picture is from the Christmas Tea with the ladies at church, and I also wore this out to dinner on Christmas Eve.

LOFT sweater dress (S) // Sam Edelman boots also at Nordstrom (8.5) // Spanx tights (B) // slip (M/L) // Kendra Scott earrings

#30. And finally, this is what I wore out to lunch with Paul the week before Christmas. The grey sweater dress isn’t exactly festive on its own, but the red coat makes the outfit holiday-appropriate.

similar red peacoat // tentree sweater dress (M) // Wolford tights (MD) // Commando slip (M/L) // Sam Edelman boots (8.5; also at Zappos) // Kendra Scott hoops // Yurman bracelet // similar WOC

Wow, that’s a lot of Jo-Lynne. If you made it to the end, you deserve a cookie… or a glass of wine, or something! I could probably go back and whittle this down some more, but I need to get on with my day. I still have my Year In Review to prep, and that one is always massive.

I hope you all are enjoying your holiday week. Stay well out there!

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