Fashion Tips & Reader Questions

Dressing Room Try-On: Madewell Fall 2019

Alright, folks, apparently we have a new feature: The Dressing Room Try-On. I spontaneously did one of these at Everlane the other day, and it seems you guys were into it, hooray! …But honestly? I think I was into it even more. It just felt like a throwback old-school blogging – you know, the kind I’ve been all nostalgic about lately – where everything isn’t glittery and perfect and staged. It’s just fun.

(I had fun.)

Madewell is one of those brands that I forget I love until I go into one of their stores, and then find myself wanting everything. Alas, it’s also priced slightly above my “Everything” budget, so I had to keep the actual purchase to One Of The Things (scroll down to see which one I went for), but still: It was all so good.


madewell painted spots pullover sweater

Painted Spots Pullover Sweater, $88

My size: M. This sweater is definitely cut to be oversized (albeit cropped), so even if you’re looking for a nice, relaxed fit, I’d buy the size you usually go with.

adore this sweater: The fit is perfect, the weight is just-right – heavy enough to be nice and cozy for fall, but not so heavy that you’ll end up all overheated and sweaty once you get inside – and the print goes with everything. (I very much want to layer this under the plaid blazer that you’ll see down there.)

madewell montford fringe pullover sweater

Montford Fringe Pullover Sweater, $89.50

My size: M

I don’t love how I styled this sweater – the fringe + florals feels a little fussy, and I feel like this sweater calls out for something super-simple and chic on the bottom. Wide-leg silk pants, maybe, or a great pair of jeans and fall boots.

The sweater itself, though, is great – super soft and zero itchy, and I like how the fringe detail makes an otherwise classic cream sweater feel extra-special.

madewell long sleeve rugby stripe shirt

Easy Crop Long-Sleeve Tee in Rugby Stripe, $45

My size: L, but I erred on the large side because I was afraid it’d be too cropped. Were I to actually buy this, I’d go for a M.  

This is the kind of shirt that I’d end up wearing every. damn. day. I only walked out of the store without it because I sent Francesca a pic, and she said “It’s really you, but it’s also just not particularly flattering”…which is exactly right. I love the shirt. The shirt is me. It also doesn’t look especially amazing on me.

(I may go back for it anyway, though. It is very me.)

madewell floral print miniskirt

Side-Button A-Line Miniskirt, $88

My size: 6. I usually wear a 6 in skirts, but this one felt a haiiiir loose around the waist – that’s OK, though, because the next size down would have felt too constricting, and it didn’t look too big at all.

A-line skirts can be tricky: They have to be cut just right, or they end up looking bulky and lumpy and adding hip action where we don’t need any extra, thanks. This skirt fit like a dream, and was a great length for getting the miniskirt look without, you know…risking showing your butt. I didn’t end up buying this only because it feels a bit East Coast to me; I want to wear it with knee-high boots and a big sweater, and just can’t see myself dressed like that in my current lifestyle. But you should! It’s so good.


madewell hi-rise roadtripper jeggings

10″ Hi-Rise Roadtripper Jeggings, $75

On Me: Size 27 – fits true to size.

Omg, these were so comfortable. Light and stretchy and very legging-ish (which makes sense, as they are jeggings). The waist hits at the perfect spot, as do the ankles, and I’m going to go ahead and say that these are the jeans that you need for an autumn denim refresh.

madewell dorset wool plaid blazer

Dorset Blazer in Navy Green Plaid, $168

My size: M

And finally: The winner.

I’ve mentioned that I’m super into blazers again (heyyyyy 2009!), and there was no way I was walking out of the store without this one. It’s actually much better in person than it is on the model – it’s perfectly boyfriend-y and slouchy without being messy-looking, and while it’s not *technically* outerwear, you could definitely wear this as a light jacket through the fall, and layered over a sweater even when it gets colder.

Tell me what other brands you want included in this series?! It’d be fun to get out of my comfort zone and test-run some new spots. 



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