The #AskAW Show: Episode 02

Have a question you’d like me to answer? Ask in the comments of this youtube video or send me an email.

Show Notes & Links

Q: I’d like to find a good pair of suede Chukka Boots, but I’ve got big feet – Size 15, can you help?

Allen Edmonds - Dundee Suede

Allen Edmonds – Dundee Suede


Q: What can I wear with my blue suede wingtips?

Dark wash jeans 


Q: How can I dress nicely in really warm weather?

Polo Shirts


Linen Button Up Shirt


Chino Pant




Q: What watches would you recommend for a guy with skinny wrists who wants a brown band?


Q: What do you think about the proportions of this jacket? story I commented on. 


Short Pants & Baggy Jackets

This article is part of my Outfit Feedback series.

I love the tailored fit of your clothes, but the length of your sweater and pants are way too short. It looks like you’ve outgrown your clothes!

My Critique

  • Right now, the length of your sweater is making your torso look small compared to the rest of your body. The key with clothing is to make sure everything looks proportional – you want the upper half of your body to look balanced to your lower half. 
  • Your pant’s inseam is way too short and is making everything look “shrunken.”

How To Fix

  • Pull down your sweater so that it hits mid-crotch (about 1.5-2” longer than where it’s currently at).
  • There’s no way to lengthen pants that much. Donate them to charity or pass them onto a friend who’s shorter than you.


The color palette of your outfit – grays, blues, burgundy, browns are great Fall colors that complement each other perfectly. The fit and break of your jeans are spot on! With just one minor adjustment, this outfit would look great. 

My Critique

  • The bagginess of your jacket is disproportionate to the rest of your outfit/body.

How To Fix

  • Definitely size down your jacket to a Medium instead of the large you’re currently wearing. The fit in the body and the shoulders will fit your frame much. much better. 

Clunky Boots, Sweater Game & Long Pants

This article is part of my Outfit Feedback series.

This is a great fall outfit. The colors and fit of everything are spot on! You mixed textures perfectly -the key is mixing textures with similar fabric weights. Normally, I always recommend sticking with 3 colors max, but think of gray as a neutral (like black and white) so it doesn’t count here. Gray, green, navy and brown make a great color palette.

My Critique

  • The boots are definitely not clunky with your slim pants.
  • Mixing textures is a good thing – it wouldn’t look as great if you had a super chunky thick sweater with this outfit.
  • Overall amazing outfit and great job!


Great sweater choice! I love the first outfit in terms of the color palette and what you paired your gray sweater with. Overall, great job with the fit of both shirts – they are the perfect length and amount of exposed shirt cuff. Jeans fit great and have the perfect hem!

My Critique

  • Black sweater is too big.
  • Jeans and shoes in the second outfit are too light for what’s going on with the upper half.

How To Fix

  • Exchange the black sweater for a size small.
  • Switch the pants in the second outfit for a dark wash or black jean.
  • Try a dark pair of sneakers or boots for the second outfit.


Love the black and white color scheme. In terms of your jeans, this is a great fit in the legs. Overall, with a few minor adjustments this can be a great outfit.

My Critique

  • The fit of your shirt is a bit too long in the torso and sleeves – it makes you look like you have a long torso and short legs.
  • Jeans are too long – they’re making your legs look short right now.

How To Fix

  • Try sizing down or switching to a shirt that is a bit shorter.
  • Jeans need to be hemmed to a slight or full break.


Love the brown boots and sneakers here. Great leather jacket as well – I would keep it unzipped because it breaks up your body vertically, allowing you to look sharper. The most important thing with clothing is to make sure that you understand what the right fit is for your body type. With that being said, here are my critiques and solutions:

My Critique

  • Pants are too slim.
  • Zipping up your jacket will create a swath of fabric which makes you look larger than you may be.

How To Fix

  • Switch your pants to a straight fit instead of a tapered fit.
  • Leave your jacket unzipped.

The fit of your sweater and shirt are great – specifically the length. The sweater should hit the belt area and the shirt should hit mid-crotch, which they do here. I love the color of the pants, but this outfit could also look great with a nice pair of dark wash jeans. Lastly, I love the clean low profile of the sneakers.

My Critique

  • Pant’s are too baggy and long – you should only be able to pinch, at the most, 1 inch of fabric on either side of your thighs.

How To Fix

  • Buy slimmer fitting pants.
  • Get your pants slimmed and hemmed to a slight break.

Do these patterns clash?



The age old question… For this outfit, yes, it does. When wearing a bold pattern, like the one on this cardigan, you want to let the pattern stand out and shine. So the rest of your outfit should be more solid or muted colors to compliment this pattern, otherwise there’s just way too much going on.

How’s The Fit of My Cardigan & What do I pair it with?

The fit looks spot on, actually! The sleeves are a tiny, tiny bit too short, but my experience with these cable-knit sweaters is they’ll actually stretch a little with wear and those sleeves will be perfect afterwards. As far as what to pair it with, see below.

What to pair it with

Should I keep this new M65 jacket?

He wanted to know whether he should keep the jacket or not. I say HELL YES! The fit is perfect, and it breaks up the black color pallet he’s wearing, as well. I really like the small band of gray shirt at his waistline. He did a great job of breaking up a huge swath of black under the jacket.

I’m not the biggest fan of his printed t-shirt, but I’m not a fan of logos or artwork on clothing in general, so it’s just my preference.

Click here to see more of the thread.