Daily Dress Me: The Good, The Bad, and the Chic

Daily Dress Me


Let’s start with the basics. My initial question, after figuring out what exactly it is, was, how did the creator get inside of my head and build the website/app that I had thought up five years ago in English class. Madness!


What exactly is it? Well it’s a website that takes the weather, and uses it to display what kind of outfit one should wear that day, set up very much like a weather forecast. It is a fashion weather forecast!


Here is a visual:



Now, my second question after seeing this is how are the outfits put together and generated. After refreshing the website on my phone various times, I noticed a repetition of outfits.




Look at the first outfit displayed in the first mobile screenshot for a clear example.

This outfit is repeated quite a few times:

⅘ days of the week, all with rather different weather forecasts, all suggesting the same thing… So with that in mind, let’s begin!!



Today, Sunday, I will start this the first outfit that was suggested the first time I opened the site:

There is going to have to be some adapting, because I don’t really own everything that any of these outfits suggest. I can fake the jeans pretty well, others are a farther reach. The Black jeweled loafers will have to be black platform sneakers. The long wool jacket will have to be a long knitted sweater. The shirt will have to be another color. Lets see what we got:


But here’s the issue:

  • It was too cold for a sweater

  • Socks are important

Thus, the outfit evolved further to:

This outfit was actually not half bad!

It was not a combo that I would usually wear ever, but with the adaptations, I was perfectly dressed for the weather!

I think what I liked about this outfit was the simplicity. Just a plain navy t-shirt with blue jeans and blue sneakers was the kind of simplicity I needed to adapt my style from chaotic-cool to refined-adult-cool. This 100% comes from the style that all of the outfits in general are, which I first saw as an issue, but I now see as a great learning experience.



Today, for the first day of reading week, it is very important to make a good first impression. How does one do that? Dress logically for the weather!!


Here is what the website gave me a lot of for today (I had to do a lot of refreshing, you will see why in a moment):

I have a similar enough jacket and heels (though I will not run to the Divinity School in the rain in heels), but no nice shirt with a collar! Apparently I am too much of an edgy teen for this!


Most of the rest of the outfits for today looked mostly like this:

I own approximately 0 jackets that look like this. I really need to go shopping. Plus, I had a lot of running around to do, so heels WON’T CUT IT.


At this point I decided to take a gander onto the men’s side of the website (that’s right! There’s a Daily Dress Me FOR MEN).


Automatically there were two Monday suggestions that worked great!

These outfits were weather sensible, and totally doable!


I went with this:

Here is my recreation of the outfit:

I had a floral bomber instead of a long blue one, a white tee just like his, black jeans, and then pink sneakers instead of his white. TBQH, this outfit was a LOOK. I was happy.

I ended up untucking the shirt adding socks for comfort, but all in all, it was a good day for the app.


After shopping one class I realized I was chilly as HECK so I swapped the white T for a long sleeve tan waffle shirt. Thus:

Thus, I was officially warm and stylish, wearing something I normally wouldn’t have, all thanks to Daily Dress Me!




After some avid refreshing, I was inspired by this look...

...to make a look inspired by, but completely different than, it!


Here’s what I got!

It’s got:

  1. Cool denim detailing

  2. Embroidery

  3. A jacket of sorts

  4. And boots!

All inspired by the look given to me.


Now, although I was pretty well dressed for the weather that day, I wasn’t very far out of my box. Probably because this is an outfit I have worn quite a few iterations of. This made me sad. But it did get the job done!




By day 4, I was starting to get the hang on this website. It wasn’t all it cracked up to be, but I was figuring it out, and today’s outfit came rather easily.

I was given:

And I gave the world:

That’s right kids, I did it all, AND THIS TIME I EVEN GAVE IN AND DID THE HEELS. AND I FELT LIKE A GODDESS THAT WAS DRESSED WELL FOR THE WEATHER ALL DAY LONG (until my feet began to hurt and I changed into those pink slides that appear in almost every photo of mine from this week). But for those two hours I slayed my version of an outfit that the website suggested. I believe that is a (two hour) win!


(But on a serious note, this website should not be expecting women to wear heels every day. Almost every outfit suggested to me all week on the women’s site included heeled booties. Yet almost every men’s look had sneakers. I find this personally sexist, and something the website really should improve upon (by adding more variance?) if it truly wants to become a usable fashion tool.)




Today’s outfit comes with a lesson: this website’s advice is best used when in conjunction with your own personal judgement. What do I mean by this? The outfit I wore today, I saved for today. Why? Because it was very obviously the warmest outfit on rotation, yet was recommended quite often, no matter if it was 40 or 20 degrees. Thus, I used my best judgement and saved it for today.



Heels, jacket, leggings, and all, as per my own personal judgement. And I was warm, but only because I manipulated the website and chose to be. So did I choose the outfit, or did Daily Dress Me? They did technically style the look, I just chose the look that best fit what I thought would work based on my own knowledge of how the weather works. Draw your own conclusions there.




I’m not sure how THIS

became THIS

but it happened and these are just the facts. I was warm, I was cozy, and I did technically wear a sweater, joggers, black shoes, and a light jacket. Just not at all the same sweater, joggers, black shoes, and light jacket. Oh well. It worked!




Now, for the sake of honesty, I must share that I wore day 7’s clothes (clothes recommended for saturday), on the next day. Here is why: I had a dance audition, and none of these were danceable outfits. Sunday’s weather was also supposed to be very similar to saturday’s. So I saved a lot of possible looks:


And I ultimately went with:

Which in turn became:

Not at all a bad look. I was a bit chilly, but seeing as saturday was supposed to be a bit warmer than sunday, the outfit was ultimately fine. Fine work, Daily Dress Me.


Now to sum up how I this week was, and how I felt about Daily Dress Me as a whole, I feel as if none other than a good old fashion, pro-con list, can truly portray my thoughts and experiences on this site.



  • Great website idea/concept (stolen straight from my dreams)

  • Very appealing and comprehensible setup/layout

  • Refresh-ability = ability to find some variance

  • Both men’s and women’s fashion


  • Only really one look for women (NYC gal on the go) and men (street style athleisure)

    • This drastic split meant men following the recommendations were guaranteed to be comfortable while women were not

    • Also, not all men dress exactly the same, and not all women dress exactly the same. There needs to be some sort of variance in style (maybe a page for “edgy”, a page for “classic”, and page for “sporty”, etc.)

  • No clear algorithm: refresh enough and any of the same few outfits could be recommended for any day of the week, no matter how hot or cold it was

    • Could be improved by making the algorithm more specific, i.e., different outfits for 30’s vs. 40’s vs. 50’s, instead of simply a range of cold weather looks for any cold weather

  • Diversity in male models but not at all in female models (race wise). Not really detrimental to the function of the website, but simply something I noticed that's pretty uncool.

  • Overall lack usability on its own (i.e. without purposeful manipulation) because of flawed algorithm and lack of style diversity.


So that was my week! I dressed how a website told me too, and ended up with a LOT of opinions.