How To Dress Comfortably While Still Looking Presentable

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I’ve mentioned before how I’ve been on a comfy clothes kick lately. But because I spend most of my days in pajamas since I work at home, when I’m out and about I like to dress up a little bit. I decided it would be fun play around with what I have in my wardrobe and share some outfits I consider comfy but still “presentable”. :) These can be worn to hang out with friends, run errands, or to more dressy events. Maybe you’ll find some inspiration here!

1. Comfy Tanktop, Comfy Shorts
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I’ve worn this basic outfit before here, although this time I’ve paired it with some comfy sandals instead of my Converse. This tanktop , while a little fitted, is just loose enough and made of a very soft material. Workout shorts are always comfortable. Rolling them up is a favorite way of mine to wear them, especially as just part of an outfit and not to the gym. I’m not sure why; I guess I just like the way that looks at the moment, but it’s also nice for hotter summer weather. I’ve worn this outfit before to my brothers-in-law’s football game, and something to cover up with was nice to have as the night got cold. A thick cardigan is a good choice, and I like the pop of this purple against the bright yellow stripes.

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Another cover-up option is a lightweight button up.

Tanktop: Love To Love, Shorts: Danskin Now, Sandals: Faded Glory (old), Purple Cardigan: Casual Corner Annex (old), Button-Up: Old Navy (old)

2. Stylish Jeggings
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I’ve mentioned before that I feel jeggings have come a LONG way. These from Faded Glory or any from American Eagle are a great sneaky, sneaky way to be comfortable while not wearing sweats or pajama pants. The first tee is in a soft, stretchy material and the second is one of my favorites because it has a wide neck (I hate most t-shirt necks because I can’t stand things that tight around my neck. No turtlenecks for me. :P) I wore basically this outfit a lot in the fall or on warmer winter days, and loved pairing the t-shirt and jeggings with these grey flats. I just think they make a basic casual outfit a little more chic or maybe feminine, while still being comfortable. I like how they look with these more deck-style flats, too, this particular pair has nice padding in the insole, and I think the pop of colors looks great with the light blue jeggings.

Though my hair is still pretty short, I’ve been growing out the top and my bangs, so some days I like to find ways to pin or pull them back out of may face that aren’t too finicky. They’re finally getting long enough to play around with, and one of my go-to ways is with either a twisted or braided across the front and bobby pinned on the side.

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I have accumulated quite a few sweaters over the years, many oversized and super comfortable. Often I’d throw one of these over this outfit in the fall. This one is a particular favorite. I love the color, the knit pattern, and the way it looks over a t-shirt and skinny jeans.

Both Jeggings: Faded Glory, Blue T-Shirt: Sonoma, Grey T-shirt: Danskin Now, Pullover: Boston Traders, Grey Flats: Faded Glory, Floral Deck Flats: Call It Spring (old) Bobby Pins: probably Goody’s

3. Jersey Knit Dress
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If you have to be a little bit more dressy (or just feel like wearing a dress) one made of t-shirt-like material is always a good option when comfort is the goal. A nice, lighweight cardigan is good for chillier days.

Another way I can keep my bangs back now that they’re a bit longer is by wearing a headband with stretch and wrapping/twisting the bangs around it to hold them in place. This is a simple single strand headband with a flower that I crocheted. You can see it worn here and here, also.

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This dress from Joe Boxer is very comfortable and the bright-colored stripes and tanktop-style bodice make it a nice style for the summer months. You can make it more casual with some sneakers, or dress it up with some nice, comfy flats.

Pink Dress: Rosebud, Grey Tanktop: No Boundaries, Cardigan: Worthington (Old), Floral Deck Flats: Call It Spring, Striped Dress: Joe Boxer (similar here), Grey Flats: Faded Glory, Shoes: Converse, Headband: made by me

4. Long Skirt, Big T-Shirt
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Long skirts have always seemed a comfortable option to me, they offer more coverage, go with lots of things, and can be worn in warm or cold months. I’m wearing this one with an oversized tee that’s nice and soft. I’m big on oversized tees right now, and I’ve also been into tucking tops into skirts lately. Paired with these comfy Dr. Scholl’s wedges, wearing this outfit feels casual while giving off a more dressy, almost 70s vibe.

T-Shirt: Arizona Jean Company (pretty sure it’s a men’s XL), Skirt: Marc Anthony (old), Wedges: Dr. Scholl’s

5. Jersey Skirt
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A jersey skirt, or one in any soft material, with a wide, stretchy waistband is great when seeking comfort, and I like that this one can be worn high-waisted or lower on the hips. Yes, it is a bubble skirt, and that may be not trendy anymore, but I for one never had one when they were popular a few years ago yet always wanted one, so I’m pretty happy to wear it (and I think it looks fine, anyway.) Skirts like this are nice with tanktops, especially more strappy ones for dressier nights. This tanktop is one with a built-in bra, so if you’re bold enough to wear just it, there’s the added comfort of less layers right there. However, this particular built-in bra is really only another layer of thin material with soft elastic underneath, so if you feel there’s not quite enough coverage (like me) you can throw a super soft crop top over it. Your crop top can be much less wrinkly, though, of course. :)

Skirt: Joe Benbasset (old), Tanktop: No Boundaries, Crop Top: One Clothing (old), Flats: Faded Glory

6. Overalls
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And finally, when nothing else works, just throw on some overalls! They’re wonderfully comfortable and can be styled in so many ways.

My bangs are finally long enough to simply push back with a headband without having them stick up everywhere, so that’s what I did here. I think pairing the overalls with this chunky bow headband and these flats gives the outfit a bit of a retro look.

Overalls: L.E.I., Crop Top: One Clothing, Flats: Faded Glory, Headband: made by me (also worn here)

Those are just a few ideas and staple outfits I wear when I want to be comfy. Hope you enjoyed!

God bless and have a great day!

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