Ah, here’s an outfit I can get behind.
While the last couple of experimental outfits have been fun, I love getting back to basics.
I’d give this outfit an A. It’s 100% my style. Everything is soft and comfortable. The dress doesn’t really show wrinkles (or anything else). I’m loving the color palette of denim blue, shades of tan, and black. And I like having the option to add or remove warmth with the denim jacket and wool hat.
I’d wear this outfit to run errands during the day — and I’d also wear it out to dinner or to a friend hang out at night. Versatility for the win!
Give your sleeves a single roll / To give the jean jacket a bit more interest, I kept the sleeves buttoned and gave ’em a single roll, just for fun. I like the exposed wrists and more casual vibe.
Try a hat / Hats have this magical allure. They seem like such a good idea, but if you’re not used to wearing them, it’s easy to feel uncomfortable or awkward.
Here’s my solution if you’re trying to get used to wearing hats:
Wear a hat when it has a clear practical purpose, like sun protection or warmth.
Don’t worry about the way it looks — simply pay attention to your hat’s purpose.
In the summer I wear a hat for sun protection, so I’ll usually take it off in a restaurant and just set it beside me — unless I was eating outside and wanted some shade. In the winter though, I usually wear a hat for warmth, so I might just leave it on the whole time I’m inside if I’m feeling chilly.
Think less about how it looks, or what others think, or the “appropriate” places to wear a hat. Instead, simply wear it when it has a practical purpose. Leave it on when it’s serving your purposes and take it off when it isn’t.
Also, look for hats that have an adjustable inner band. That way, you can tighten it when it’s windy outside and you won’t have to worry about it blowing off.
I’m curious, do you feel confident + comfortable in a hat? Did it come naturally to you, or did you have to get used to it for a little while? Got any tips for us? Share away in the comments.
TWO more outfits to go, and then it’s recap time on Friday. We can do it!
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Liked today’s outfit? You can shop it and support Unfancy at the same time by using these affiliate links:
01 | Dress (old) | Similar (made responsibly) | Similar (made responsibly for under $55)
02 | Denim jacket (old) | similar | similar under $75
03 | Shoes by Madewell (on sale) / similar (made responsibly) / similar slide (made responsibly)
04 | Hat by Hinge (Fit note: It’s got an adjustable inner band!)
05 | Bag by ONA
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I love this outfit. I especially love your tips for transitioning into hats–I could only get comfortable wearing them when I knew they were protecting my eyes! Thanks for sharing!
x, Tyler | http://tinymisstyler.com
I always had too much to carry around in college, so on rainy days I couldn’t juggle all of that AND an umbrella, so I began wearing a waterproof hat (fedora-style). Since everyone else was tucked under umbrellas, it was easy to feel that no one was staring and to grow comfortable with hats.
Heather, that’s the perfect excuse to try one! :) xo, Caroline
I’m from Brazil and your blog is really inspiring for me!
I also have a blog, and some of my outfits are very much similar to yours :)
By the way, here in Brazil we usually don’t wear hats, but I love to wear beanies when it’s chilly :)
Hi Anne! Very cute style, thanks for sharing :) xo, Caroline
Rachel Tuggle says
How do you avoid the dreaded hat hair look?
Krystal Nelson says
Hat hair is a total downer!
Before I put my hat on, I part my hair on the opposite side (switching my left-part to a right-part) and then flip my hair back to normal once I remove my hat. It’s not foolproof, but my helmet-head isn’t as bad!
Hey Rachel! I usually wear my hair with a wave in it, so most of the time, hat hair isn’t super noticeable. I usually get hat hair when I really tighten the inner drawstring, so I try to leave it loose unless the wind is really picking up. If I do have to tighten it though, and end up with some hat hair, I just try my best to shake it out real quick — either shaking it out with my hands or a quick flip upside down if I can. It’s not always perfect, but that’s how it goes sometimes, right? :) I haven’t down this, but you could keep a travel size can of dry hairpray in your purse for a quick fix. Hope that helps! :) xo, Carline
I love the look of big, a bit floppy hats like the one you’re wearing. However, when it’s cold, I’m usually more tempted to wear a big scarf, and then the scarf will tip the hat over. I haven’t found a perfect hat/solution for this, so for now, I just use beanies in the winter and hats with brim in the summer!
Thanks for sharing this outfit! Love the jacket.
Vivi / avecvivi.com
Hey Vivi! Whatever works, right? I love beanies in the winter too, and you can’t go wrong with the big chunky scarf! :) xo, Caroline
Love your thoughts on focusing on a hat’s purpose! I bought one at the beginning of the year while I was on vacation, and for some reason I found it so much easier to wear while I was out of town! I’m getting used to wearing them, but it’s taken time for me for sure. Loved today’s look!
I love hats! I started wearing them when I got a Panama hat for a tropical vacation and it was then that I realized- the greatest thing about hats is not having to do anything with your hair! Because I loved that little perk, I got a felt floppy hat for Fall last year and wore it every time I didn’t have time to do my hair, every time it rained, and whenever I’d be out in the sun. Al the practical stuff like you said. I get so many compliments when I wear hats that now I feel completely comfortable wearing them. I wear them often enough that some people consider me a “hat person.” So it’s sort of become a signature look for me now.
Hi Stacy! I love that! Just goes to show when you try something new, you might love it :) xo, Caroline
Tanya E says
Nice outfit! I do like hats and have branched out a bit in styles. I am pale, so need a sunhat in summer, but it’s taken me a while to find ones I like. I have a leather Australian hat (similar to a cowboy style) which is heavy enough for beach/walks and not get blown off and a straw fedora which is smarter which I have worn lots.
For cooler weather I have got out my felt fedora now (which I am going to put tape inside to make it a snug fit). I also have a baker boy style cap in wool and lots of beanies (it gets cold here in the uk) of various weights and warmths and a beret. Great advice about when to wear a hat and as for hat hair, I tend to just tousle my with my hands to fluff it out again.
That is a great idea for trying out hats! I love the look of them but haven’t found one that I love. I do wear baseball hats to run errands on the weekends, and while I do pick cute ones it isn’t a fashion statement so much as comfort and not washing my hair as often ha.
Have you ever heard of the brand Lou & Grey? I feel like it looks like your style. They have a small section of the brand at Loft but also have their own website and stores. Everything I have bought has been SO soft and comfortable, and good quality.
I love wearing hats, especially big floppy ones! I think they complete an outfit for me. They aren’t very practical in the heat & humidity of South Louisiana, but once Fall hits I plan all my outfits around which hat I want to wear.
Lynn herrick says
I am all about the hat – here in San Diego, it makes all the difference. I think it is super important to invest in a hat that can be folded for traveling – JCrew, Tommy Bahama and Lucky make great travel hats. It is also the perfect compliment to a summer outfit. I always get compliments.
Hey Lynn — that’s so smart. Would definitely come in handy for travel, especially if you can pack it without damaging it! :) xo, Caroline
Caroline, I love how much you’re posting outfits lately! These are so fun.
I just got my first hat in the mail yesterday! I’ve gotten comfortable wearing a baseball cap, but this is my first fedora-type hat, so I’m a little nervous to wear it out. Fortunately, I’m headed to NYC in a couple weeks, which seems like a good place to give it a go!
Hi Stacy! That sounds like the perfect opportunity to test it out :) xo, Caroline
I love everything about this outfit and post. It feels true to your style and relates to my own. Definitely wearable in the humid + hot southeast fall for me! The jacket and hat give a nod to cooler weather while the dress keeps things nice and breezy as the temps rise in the afternoons.
I’ve been following your blog from nearly the beginning and this outfit is easily one of my favs, definitely in the top 5!
I enjoy wearing wearing hats when I find the right fit for my style and face shape. Sometimes I steal my hubby’s wool caddy cap in fall and winter. :)
Gorgeous – this is my favourite so far. And the hat makes it.
I have this dress in navy, and I wanted to ask a question. I took it to wear to a formal dinner recently, and it was incredibly clingy. I had to do a last minute repurpose of an inner slip from another dress as I didn’t have a proper slip with me.
So – how have you washed it? And are you finding it static-y?
Hi Cass! I had someone else mention the same problem! I wonder if it has to do with the climate? I haven’t had any major issues with it. Lately, I’m mostly hand washing and hang drying. And typically when I battle static cling, I either use a spray like Static Guard (http://bit.ly/2cUqYVd) or rub a dryer sheet along the inside of the dress. That seems to help :) xo, Caroline
Personally, I just can’t do hats. Even when they have a practical use. I generally choose ears over a hat. Even when I went to the Kentucky Derby, and lots of people were wearing hats, and it was practically useful for sun protecting, mine didn’t last more than five minutes on my head. Maybe its psychological from having to pin idiotic dance costume hats onto my head as a child…
Gabby, haha maybe you were traumatized! But yes, as with most things, hats aren’t for everyone. :) xo, Caroline
love..love… hat + denim jacket combo!
I wish I could pull of a hat as well as you!
Hi Eloise! I’m sure you just need to find the perfect one for YOU and you’d pull it off beautifully :) xo, Caroline
Madeline | mad's Muses says
Love this outfit! Definitely versatile and my style, too!
I love hats, though mainly knitted beanies in winter or straw hats in summer am considering branching out into a wool brimmed hat. I have to say though if its cold enough to cover my head I’d need my legs and toes covering too so this outfit won’t work in the Uk Autumn, but with leggings or tights I’m all over this! Back to your point about keeping our wardrobes relevant to the life we have, not our imaginary or fantasy one!!
Hi Rachel, I think tights would be an adorable twist on this outfit! Good call :) xo, Caroline
I love your hat!
Mireia from TGL
Hi Caroline, i really love hats, but I am afraid that I can only wear it with my hair down, and not with a ponytail or other hairdos. Any suggestions are always welcome!
Hi Eliene! I tend to keep my hair down with hats as well. I think it just looks nice having something to frame your face. But that being said, if you do pull your hair back into a ponytail or low bun, try leaving a few face-framing pieces out in front, and see if that helps! :) xo, Caroline
thanks a lot for the advice!!
I’m a total hat person! I think the easiest way to ease into wearing one is to throw a baseball cap over a ponytail. Perfect for football games or an errand where you’re not in the mood to fix yourself up. In the winter, beanies are my jam. They’re so darn cozy and cute (and like you said, practical!). I felt a little conspicuous in my woven hat over the summer, but I continually got so many compliments on it that those feelings didn’t last long. Just remember, most people are too self-conscious about themselves to focus on you anyway. I find that comforting, hehe. :)
Hey Taryn, excellent advice! :) Thanks for sharing! xo, Caroline
I’ve been living in my denim jacket! This outfit is perfect for running around town in :)
Alyssa J Freitas says
When I was younger I would wear a variety of hats daily! I had the most confidence with them and have been getting back into throwing on a hat when I remember to :) In the winter I tend to wear one most days but always feel like I have to take it off during class. Maybe I’ll be more inclined to keep it on from a stylistic point in the future.
This is similar to what I wore today, except I wore a stone open-weave cardigan instead of a denim jacket and my flats were close-toed. This is probably the last day this year that I will wear a dress without tights. No hat. We can’t wear hats at work.
I am loving the remix challenge and agree that this outfit is an A for sure :-)
Being a very pale girl in Australia I am a BIG hat person! I do have a massive head however (thanks Dad) so lady hats sadly never fit. I love a baseball cap for sunny days and am currently saving up for an Akubra (Australian made ‘cowboy’ hats that come in a range of very cool, non-cowboy, casual styles).
High five for sun protection!
the minimalist bohemian says
Ohhhhh I LOVE this outfit! This gets an A+ in my book. Especially loving that hat.
baseball hats and knit hats for winter give me life on the weekends. I think I have 15 of each.
Ohh, the hat part is right to the point! I’ve just bought my first hat and was brave enough to wear it outside the house (you can see me wearing it on my IG http://www.instagram.com/sasha_zeen). It was a definite step outside of my comfort zone. Somehow I thought that I will see many more people wearing hats (like I always do) and feel like a part of the club. Alas… I only saw one more girl with the hat. And she wasn’t even wearing it, just holding in her hands. So I did just what you said – I thought to myself “OK, it’s kind of sunny and windy. The hat protects my face from the sun and keeps my hair from flying around in the wind. And it’s cute! You know it suits you. So, who cares if you are the only person in the city who wears a hat?” That kinda helped! lol