Article Line Long1
Design

My Favorite 2021 Fashion Styling Hacks/Trends – A Step By Step How To Make Your Comfortable Clothes Look Like You Still Care

I feel like there is a hole in the market for fashion inspiration for normal people, or more like people who care just a little about looking stylish on an everyday basis but don’t necessarily want to stand out at school pick-up or when running errands. We simply want to be comfortable, but not look schlubby or lame when/if we leave the house in our comfys. And most of us aren’t models so we don’t feel comfortable with the crazy trends that often just look dumb unless you nail it (good for you if you do!). You saw my ‘fall’ uniform a couple of weeks ago but this pulls out what I find to be the fastest and easiest way to ‘edge up’ anything comfortable and basic. Not a fashion guru over here and shooting this made me LOL a lot. I used to live next to Suzanne, who works at The Great and just always dresses effortlessly cool and would help me, but now I’m on my own. Listen, I’m trying and I’m not sure I nailed it, but we can all see for ourselves below (and also WHO really cares?)

The Sock And Sleeve POP

Sweatshirt | Striped Shirt | Jeans (similar) | Beanie | Boots | Socks (no longer available)

For the first outfit, we have a classic quarter zip, and my favorite jeans that I’ve had forever. But I can’t leave the house like this so here’s what I do – it’s a real hilarious step by step:

  1. Put on a patterned sock, one foot at a time. I like to start with my right foot, but please honor your own personal preferences.
  2. Roll up the pants so you get just a pop of a green striped crew sock. The pattern is crucial – not just a solid dark sock please.
  3. Grab boots that are fitted at the ankle (like my Doctor Martens)
  4. 1/2 tuck the sweatshirt into your waistband. Duh.
  5. Reach into your sleeve and gently pull your long-sleeved striped shirt out so you can see 3-4″ of pattern. No more or you could be arrested.
  6. Shove your sweatshirt (with shirt) up almost to your elbow.
  7. Add a textured beanie so you don’t have to do your hair, one that has a bit subtle pattern for extra credit.

DONE. YOU ARE WELCOME.

1. Hansel From Basel Love Crew Socks | 2. Men’s Striped Crew Socks 3pk – Goodfellow & Co™ | 3. Women’s Marled Crew Boot Socks – Universal Thread™ | 4. Assorted Crew Socks (Pack of 3) | 5. MWL Cloudlift Sneaker Crew Socks | 6. Ella Collegiate Knit Sock

1. Slim Perfect Long Sleeve T-Shirt | 2. Women’s Striped Long Sleeve French T-Shirt | 3. Women’s Striped Long Sleeve Boat Neck T-Shirt | 4. Long Sleeve Thermal Top | 5. Tissue Turtleneck | 6. Truly Madly Deeply Frances Striped Tee

The Striped Crew Sock + Duck Boot + Tailored Wool Look

Ok, so you have your black stretch pants that you wear every day whether or not you work out, and we all have a slouchy sweatshirt. But you want to go to the farmers market and you might run into followers/readers. What do you do?? This?

Boots | Coat (similar) | Sweatshirt (similar)

I have worn this so many times, guys. Dropping off kids, popping by the farm, over to Fred Meyers. Here’s how you do it:

  1. Take tall crew socks (these are mens via Target) that have a retro stripe. Sure you could also do a different pattern but it shouldn’t be the star. (see above for more options)
  2. Place them OVER your stretch pants (I KNOW, I KNOW CRAZY) like leg warmers, then slouch them down. You need to be able to see the stripe, but it shouldn’t be straight or too tight.
  3. Throw on your duck boots (the “it boot” of the year). I got mine from L.L. Bean and I LOVE THEM. The zipper means no laces and you know how I feel about laces.
  4. Throw on a baseball hat – bonus points if it’s a small business or local merch. I love Skypark so much and it makes me feel close to Santa to wear it (it’s the year-round Christmas-themed adventure park (obviously) in Lake Arrowhead that I’m obsessed OBSESSED with). But I’ve started picking up cool hats from Breweries up here. I like the mesh ones that are adjustable because I like how they are slightly oversized.
  5. You can stop here OR you can even throw over a trench or tailored wool coat. Why not? I mean, obviously, a fleece works too, but don’t be afraid to pull out something that leans “menswear” even if it’s kinda tailored.

1. Leopard Print Coat | 2. Averdon Coat | 3. Women’s Plaid Double Breasted Overcoat | 4. Cozy Wool Blend Puff-Sleeved Coat | 5. Women’s Relaxed Fit Top Overcoat | 6. Houndstooth Quilted Long Coat

The Difference A Pair Of Vans And A Fanny Pack Can Make

The punch-up of the classic checker vans really works. I wear them with my sweatshirt onesie and it feels like an outfit (whereas normal cross-trainers or running shoes could look dorky).

Jumpsuit | Bag | Shoes

  1. Put on cool sneakers. Again, one foot at a time is recommended by our pediatrician.
  2. Put a belt bag over your head, then adjust to one side almost like it’s your armpit’s personal purse – this could be a fun leather one OR even just a more utilitarian one. I just like how they look, that is all. It feels weird wearing a “purse” with a sweatsuit but if you don’t need a big bag then what? The fanny pack that is what.
  3. Pull up your sweats to mid-calf – I have no idea why this is a thing, but it looks less schlubby, it just does.
  4. Repeat step #3 only with your arm sleeves. 1/2 way up to the elbow is advisable.
  5. Add baseball hat or beanie so that you don’t have to think about your hair with the humidity. Ideally, your hair is in a ponytail because if you have it down then go out in the rain you can look like a character in Wayne’s World when it gets curly. Pony + face-framing pieces. You know, like the Fronch.

While I don’t do too well with laces because I’m a toddler, I am eyeing a few others to shake it up below. Some classic waffle Nikes (gotta represent up here) and a couple others from Sezane, UO, FP, and Madewell (and while I think that Converse does the same thing I just can’t with how flat they are and how long it takes to lace up the high tops). I personally stay away from anything too white living up here. I’m LOVING these darker browns/blacks and greens – they feel fresh and not too ‘mom on the way to aerobics’ (not that anything is wrong with that).

1. Fanny Pack | 2. Leather Fanny Pack | 3. Desta Belt Bag | 4. Zip Closure Fanny Pack | 5. Mare Belt Bag | 6. Bella Belt Bag

1. Alex Sneakers | 2. Nike Daybreak sneakers in black | 3. Checkered Slip Ons | 4. Nike Waffle Trainer 2 | 5. Veja Dekkan Sneakers | 6. Gola Badminton Court Sneakers

The Baggy Jeans And Oversized T-Shirt Trick

Pants | Shirt | Sweater | Beanie | Bandana | Bag | Boots (similar)

This one I think looked better without the hat. I think I have slightly too much going on, but here’s what I did.

  1. Roll up pants to be high enough to show your sexy ankle. If you are from the Victorian era you might be offended at this notion. But with baggy jeans, you need to some some ‘leg’ to play with proportions.
  2. Put on tight boots that tuck in under the jean- a lot of shooties do this – or if they are elastic. They pipe right up your leg in just the right way. Work that sexy ankle shootie.
  3. Throw on a cardigan – I’m into oversized grandpa boxy ones on my frame. This does not need to be your grandpa, it could be a friend’s grandpa or if you see a grandpa on the street and you like his sweater you could offer to buy it. Just offer a fair price.
  4. I ALMOST FORGOT TO TELL YOU TO 1/2 TUCK YOUR SHIRT – PLEASE DO SO IMMEDIATELY.
  5. Apply bandana. I like doing this loosely, almost haphazardly because I’m lazy and don’t have a ton of patience. I like the knot to be in the front or to the side.
  6. WARNING: DO NOT PAIR BANDANA WITH BASEBALL HAT. I did this last week and was mistaken for a boys scout. True story. Almost.
  7. Add crossbody bag with pattern (Madewell has straps you can buy to put on any leather bag). I love this one very much.
  8. Add simple beanie, maybe. Maybe not.

Listen. It’s cool to be comfortable. Full Stop. Maybe these little things will help us feel slightly more stylish? Maybe not. 🙂 ALSO IT DOESN’T MATTER LET’S JUST HAVE FUN IN LIFE AND TAKE IT ALL LESS SERIOUS MKAY?

0 0 vote
Article Rating

WANT MORE OF WHERE THAT CAME FROM?

Never miss a single post and get a little something extra on Saturdays.

36 Comments
Oldest
Newest Most Voted
Inline Feedbacks
View all comments
MKP
1 month ago

Honest to God, this is VERY helpful to me. You made it so fun and funny but it is exactly the post I needed. I was literally just thinking yesterday about how I have tried so hard over the years to care a little about fashion/my appearance, but I guess I just don’t care enough to make any real effort. And then I remembered that I used to just have a little “edge” and that’s what’s gone missing. I like simple, comfortable clothes but miss having that edge. I sort of wrote this off as not possible (for me to figure out anyway) and then Boom! This fashion post. I really really REALLY appreciate it and please do more. Keeping them also light and a little sarcastic because truly, it doesn’t really MATTER if I wear a patterned sock and fun boot with my jeans and sweatshirt, but why the hell not?! I seriously love this and if anyone knows of where I can follow to give me more od this, please share. Thank you! Loved it.

Kara
1 month ago
Reply to  MKP

Same! All of the above! Who should I follow? I do follow @karlareed and she gives great styling tips just like this, HOWEVER, her style leans more preppy than mine so I would love to find an edgier version of her to get the styling tips with clothes that match my personal vibe more.

1 month ago
Reply to  MKP

i feel like the word ‘fashion’ is off-putting and gives off the wrong idea (at least to me?) – it’s all about style and what suits yours and makes you happy! after going on a no new clothes trip (that has yet to end) i’ve learned so much about mine – it’s all about utilitarian comfort and and what brings me joy. accessories, layers and the little things are where it’s at – purple shoelaces b/c it’s my favorite color, a folded cuff (that’s actually v. useful in muddy/wet places lol) / tucked in tee, a favorite coat w/perfect pockets, and grandpa sweaters that feel like blankets, etc, etc. i share my style here (it seems similar) and on my blog. also, the nothing new / slow fashion ig community is awesome 🙂
ps. hilarious post emily! it’s definitely cool to be comfortable.

Meredith
1 month ago
Reply to  MKP

MKP, the frisky_gato wears whatever the hell she wants and I love it. Find her on Instagram. Cup of Jo also regularly features women with unique style, if you aren’t already reading her blog.
Emily, the first rule of Converse is that the dirtier they are the cooler you are. Who cares if they get dirty! Lol.

K
1 month ago

Oh my goodness, this is brilliant and exactly what I need. I don’t want to look like Christian Girl Autumn (I am Christian, and that’s not meant as pejorative, just a funny meme) OR like a UO model, but I have a hard time finding the in-between. PLEASE more of this and the step-by-step is honestly so helpful in breaking down what works and how to apply it to other outfits.

Most moms of young kids I know feel like they’ve lost their coolness, and this feels like tips to recapture the feeling you had when you were going to a concert that started at midnight when you were 22.

1 month ago

your site is very interest thanks to a lot.

Kristin
1 month ago

100%. Everything about this post 100%. Thank you!

1 month ago

This is so me, as well! Why not take a couple of minutes to up the edge? I use scarves, hats, booties (or sandals) with abandon, ha! Love seeing your take.

Cris S.
1 month ago

So well written and hilarious! But also helpful in thinking of little things to do to edge things up (but in a way that prioritizes comfort yay!). One of the earlier commenters mentioned young moms – well, some of us old moms never got our mojo back over the years either. This will be helpful next time I get together with my “cool” friends. And may send me back to the store for the shooties I left behind yesterday. Thank you!!

DeniseGK
1 month ago
Reply to  Cris S.

Same! I’ve been without mojo for 16 years and after seeing nearly no one for 2 years, I’m ready to rock my own actual style when I’m out and about. Life is too short for me to worry and hold back anymore!

One thing I considered with some of the outfits that I wouldn’t wear myself is that the extra stuff Emily adds to “edge it up” would be good present ideas for my friends who have a style that is very much on the same wavelength as Emily’s. I’ve been busy with kids and a house that might be suicidal, lol. But I have a diverse group of friends, and even the ones with no children and sometimes no partner (by choice!) have been swamped with other things. A career can really take it out of you, caring for aging parents by yourself will too. So I think this post is good for people in all walks of life.

1 month ago

I also really appreciate your advice and suggestions on how to piece things together. I love your “comfy yet put together” style and you are often an inspiration for what I buy. I also prefer to be a little quirky, outdoorsy, laid back, grandpa-sweatery, PNWish (where I also live) and you also guide in that direction. Last, I feel this style works for a wide range of ages, and so that’s also good as I am a few years older than you (-: Keep doing what you’re doing, and…. thank you for your ideas!

Kristi
1 month ago

Fun! Next time could other staffers play too? Fun to see tricks on slightly varying body types/ heights.

Ashley
1 month ago

This post is for real so helpful! As a new mom I struggle with just looking schleppy all the time but putting together full trendy outfits is just not the stage of life I’m in. Slightly leveled-up basics/comfies is exactly what I needed! Thanks!

Rusty
1 month ago

While this was written tongue-in-cheek, it’s really helpful!
After not evvvvvver being alone for 11 years, I haven’t been able to buy a single piece of clothing, shoes, anything (or underwear, for that matter😳) that I like.
It. All. Had. To. Be. Approved. = boring, plain, no pattern, no writing on anything, no logos, etc.
Now that I can go shopping and be more my authentic self, I don’t have much of a budget, but I like thrift shopping!
Buuuut, I don’t have a car!!! I just bought some new sneakers and I was so rushed, because someone took me and kept looking at the time, I bought the wrong size! Now I have new sneakers that don’t fit properly and I can’t even get to take them back! Gah!🥴
Soooo, this post helps me think laterally about what I already have which isn’t much, but maaaaaaaybe I can edge it up?!?🤗 Gonna give it a go!

Mistymountain
1 month ago
Reply to  Rusty

So glad you are now FREE to live and shop now ! You can trade.give away or sell your sneakers online at a resale site – a great place to browse a million styles and prices to zero in on what makes YOUR hear sing!

Rusty
1 month ago
Reply to  Mistymountain

Oh, thank you, Misty😊xx
Thrift shops where I live in Australia aren’t really online, but I love the idea.
I’ll get there. I’m working on getting a 2nd hand car, but my budget u5s super tight. Then I’ll be able to go shopping!

Kara
1 month ago
Reply to  Rusty

Poshmark just opened up in Australia for thrift clothing shopping. 🙂

DeniseGK
1 month ago
Reply to  Rusty

Oh, Rusty, that sucks! People who offer or agree to do favors should do them with grace and a good attitude. I don’t know if Australia is too different from where I am, but I have had a little success with calling a local store and getting them to let me mail something through local snail mail to them for a return. The manager was able to decide that they would be willing to do that – don’t know if managers have that freedom in every company or culture. It might be worth it to try? Anyways, I hope the next person who helps actually acts like a caring helper and treats you with basic human decency.

KZ
1 month ago

Damn you Emily Henderson!! You did it again. I didn’t even know I needed this advice!! But I do and I love it. Details matter!! And you are hilarious and charming as always. I laughed for a solid minute on “Fronch”. Now I have to figure out how to apply your techniques here in Southern California where the blazing sun doesn’t allow for all your layers. I’m jealous of your cooler temperatures. Great work here 👏🏻👏🏻👏🏻

Roberta Davis
1 month ago

Nice tips and I will try some of them, but I always feel like I look dumb and awkward when I try to be cool like you.

HH
1 month ago
Reply to  Roberta Davis

Same. Or if I’m being casual “cool” I feel like it looks too forced. The funny thing is when I’m in my dressy or casual dressy mode, I don’t feel like this, but as a pregnant, teleworking, mom of a toddler, I don’t have a lot of desire or need to dress up.

DeniseGK
1 month ago
Reply to  Roberta Davis

I used to get this feeling when I was still trying to figure out my style. I thought I would be able to find someone else who would dress exactly like what I want and I could just copy them. I think we all have to tweak it. We can find someone who is close enough to be a starting point, but then we have to change a little this or that until we feel cool and confident without feeling like it’s awkward or forced. Keep trying, I believe you will get there!

Millie
1 month ago

Love this post, and can I ask a sock question? Am I the only one who has issues with socks sliding dow below my boots??? I want them to look fun but need them to stay in place! I don’t have the energy to be yanking my socks up all day! Advice? Brands? Thanks from an almost-40 mom of four kids! 🤪

S
1 month ago

Wasn’t Suzanne going to write as a contributor? I was holding my breath.
her style is the best of the best

S
1 month ago

Whoa! Someone suggested @karlareed so so good. This is just what I need. More of those!
I follow lecatch
I need more pizazz.

Julie S
1 month ago

First of all, hilariously written, probably my favorite and most useful fashion post to date (I often skip them). Second of all YES by all that is good and true we need this. I don’t care about fashion per se, but I do want to look like I have a little bit of a clue as to what waistlines/hemlines/silhouettes are doing, while being comfortable and not having to think too much about getting dressed. There are some good influencers doing this kind of fashion info so it’s out there- I try to check in with these blogs a couple times a year for fresh ideas and keep a finger on the pulse for “in” things that work with my short petite proportions. The half tuck, rolled jeans, and exposed socks/sleeve edges are all in my playbook too.

Julie S
1 month ago
Reply to  Julie S

PS As far as recommendations, off the top of my head I have browsed Get Your Pretty On, Frump Fighters (geared to tired moms), and Extra Petite blogs/insta for fairly realistic outfit tips and inspiration.

Rusty
1 month ago
Reply to  Julie S

Thanx for these🤗

1 month ago

“Amazing write-up!”

Li
1 month ago

Ok, I love this. It’s not BUY THIS THING TO LOOK COOL, it’s a try these tips to look like your trying and not just rolling out of bed. Love love this. More attainable fashion posts!

jasmine
1 month ago

how fun, I love this!! 🙂 I think the tailored coat or jacket is so good for hiding every shlub sin. I once saw a friend in the supermarket at 7am and she wore pajamas (!) but she had buttoned a knee-length wool double breasted coat, over the top. With her tousled bun and bare skin, she looked incredible. I’ve never forgotten haha. I keep a knit blazer at my desk which I throw on over anything, even a striped tshirt, and it instantly elevates not only my zoom calls, but my general outlook! Also – as a parent, I can’t stress the perfection of the striped button down enough. It hides stains and the collar makes everything better.

Ashley Y.
1 month ago

Give yourself more credit … You totally nailed it! I appreciate finding a fashion blog that doesn’t take itself too seriously, and your sense of style AND humor really brightened my day!

Molly
1 month ago

I’m a little late to the party, but I have to add the most essential tip to elevate your comfiest (for me) is put on your jewelry! Particularly hoop earrings. Great post!

Tamanna
1 month ago

LOVE THIS. also a new mom who has suddenly gone from cool funky style to….no style. such easy tips! also i’ve been on the hunt for a cute beanie that will not look huge and make that condom tip top on my small head…..sources? anyone? (you know what i’m talking about here right?! not cute!) i never click on anything fashion related, so thanks for this post.

1 month ago

Ok looks like huge different between two photos but just 1 or 2 pieces.. Amazing post

1 month ago

Really enjoyed reading the blog. Great website!

Go To Top