Hahah :) man to woman I’ll do my best. Keep in mind my female fashion advice stems purely from my own taste in women, so I can’t express the absolute validity of what I would call the “female wardrobe essentials“ (at least as far as actually acceptable womenswear)

If it were up to me, all women would wear cute leather shoes, boyfriend jeans, white cropped Ts, and top buns.

Per usual start your search in the local thrift shops for some genuine vintage that won’t break the bank, but here are my thoughts.

A MAN’s GUIDE TO #WOMENSWEAR ESSENTIALS:

SHOES:                                                                                  

(fall/winter) - You’ll want some boots for the wet and snowy weather. If you can swing it get some Bean Boots, and if not spend some time looking for sweet vintage leather Sorel Boots. Or some original tall Hunter Rain Boots (stick to subtle colors) as this is a lifetime purchase, you’ll regret getting something obnoxious.                             

(spring) - Some pretty generic leather ankle boots for everyday wear (like these). For less functionality but more class, get these Willem wedge booties from J.CREW (in sandstone).                                

(summer) - If you aren’t down with rocking bare feet, I’d say you have three really sweet options. Arizona Suede Birkenstocks (in taupe) or any of the other suitable natural colors. Some narrow strap, premium leather, Rainbow Sandals (dark brown or sierra). Or some organic Keds lace ups / some classic TOMS (olive).

BOTTOMS:                                                                                              

(fall/winter) - Boyfriend jeans. Boyfriend jeans. Boyfriend jeans. I honestly cant say this enough. Take his old shit and use it to find someone better. But seriously though. Plus it’s cold out there, just because you’re a girl doesn’t mean you have to freeze your buns off in skin tight skirts. We’ll understand.                                                  

(spring) - long skirts and pencil skirts from JCREW, designer skinny jeans, and raw denim A.P.C.                                                                              

(summer) - Spend all your time in rompers. I can’t give advice about this because in reality I know nothing about womenswear, but do your research, and find one with a hot print that fits you really well. Also jorts. Never ever buy them. Take your old jeans, cut them well, fold them well, wash them a few times, and belt that shit. Some pretty good tutorials exist, check GQ for one about mens khaki shorts.

TOPS:                                                                                                       

(fall/winter) - WEAR AT LEAST THREE LAYERS AT ALL TIMES, unless you’re naked or wearing a bandeau and blazer in public.                        

(spring) - cotton tees at J.CREW, pocket cardigans at COS, cheap blazers at Urban Outfitters.                                                                        

(summer) - whatever you’re wearing now, but cut it up.

Beyond that, get a few bags like these or these. Try and cut down on carrying a traditional purse. THROW THAT HAIR IN A TOP BUN… 

and come find me so I can take you on a date.

THESE / THESE (in warm sienna) / THESE or THESE (in cognac) / or these which aren’t brown, leather, knee-high, or boots, I just love them.

Now I can’t totally support the validity of my answer here, given that my taste in women’s wear is almost entirely based on what I find attractive haha, but even so, winter coats are actually something I know a lot about so I’ll do my best. You could also always ask the lovely Sam, Kat, Becca, or Nicole.

My two pronged approach to winter outwear is obviously, form vs. function and a pleasant combination of the two.

First of (per usual) hit the thrift stores. Particularly in bigger cities, you can find everything from North Face to Burberry at a fraction of the cost if you’re willing to look. Especially because it is SO EASY to spend exuberant amounts of money on a nice coat.

COS Belted Wool Coat - #comfybathrobesteeze #affordable

J.CREW’s Academy Coat - I know I always play the same tune, but 9 times out of 10 the quality is spot on for the price. I know toggle is supposedly really cool, but im not really into it. I love the classic double breasted, and though you wouldn’t get the break in price, I’d suggest rocking the sandstone color.

Barbour’s Ladies Beaufront Waxed Jacket - I realized this seems like a weird suggestion, but again it plays into my personal taste. Wearing a more masculine jacket in shape/style/color like this gives the unique opportunity to maintain exceptional functionality, while being able to flaunt femininity. You could basically go swimming in this coat zipped up and secure. However, let it hang open and pair it with some highwaisted slim jeans, maybe a simple white crop top and some tan suede booties for a gorgeous natural look. In my opinion its all about balance.

Belstaff Roadmaster Jacket - “The epitome of rugged, authentic cool.”

Just to through it in here (if you’ve got a grand to throw around) and only if you’re super tall, grab this Edith Harris Tweed from Whyred

Patagonia’s Powder Bowl Jacket - You won’t be wearing this one to Fashion’s Night Out any time soon, but you will be warm and cozy skiing off cliffs of powder at Alta and blowing through trees in Vermont backcountry.

North Face Down Destiny Jacket - Every human needs to own a North Face Down Jacket. Buy it in black, wear it for your entire life, then send me a “thank you” card for making you a better a person.

A mans flask says a lot about his character. I personally have one wrapped in cork that I picked up in Boston a few years ago. It has a story behind it, it maintains a masculine aesthetic, and it serves its purpose without fail.

You want a flask that has the perfect balance of, “I love scotch. Scotchy, scotch, scotch. Here it goes down, down, into my belly,” and, “Why yes, as a matter of fact I AM James Bond.”

Per usual my first suggestion is this one from JCREW. Though I dont think they monogram and the imprint “this way up” is kind of lame flask ciche, it’s super high quality and the leather patina is gorgeous.

I’m also a big Etsy supporter because if you do your research, quality is super high via. the more personal craftsmanship, and the price is usually awesome. Here’s one shop that does custom monogramed, leather wrapped flasks based out of Illinois, and her stitch detailing is pretty rad.

There’s also In God We Trust. Their flask isn’t leather wrapped, but is high quality and they do really cool custom hand engraving.

Then totally straying off the path of practicality, and having anything to do with what you’re asking for, is this. The Malacca Flask Umbrella by Swaine Adeney Brigg, the most ultimate of badass #menswear #status accessory a man could every own. If you’ve got like 600 dollars kicking around, fuck the leather flasks, this bad boy is for you.

Before I say anything, I will always push second hand / vintage wear. It’s  10x more affordable, and if you really look, you CAN find what want. Look for brand, fit (or ability to be tailored), and versatility / function.

That being said, I have a two pronged answer for this:

1. Every man should own a new, real “rugged” rain jacket, more than a duffle coat or a wind breaker or whatever light coat you may own, for those days when its really really wet (like the hurricane we’re currently preparing for), or when you’re on an adventure through the wilderness. Something you could feel safe and warm in after diving into a swimming pool.

- for this, to be honest, I’d really suggest any L.L. Bean raincoat. I have an old version of this one and I wouldn’t trade it.

- if you want to get a little more stylish, but still have a jacket that will literally hold up through anything, go with a traditional RainMac / Mackintosh. Its been around forever for a reason.

2. I have a total weakness for coats, so it’s difficult to pick something out new, with really high quality, that is also affordable haha. To be honest though, a really nice jacket is something you want to shell out the cash for. So my suggestions for more form over function are:

- J.CREW - I would cosign literally anything they have to offer. I have this one, its super warm, but also breathable, and fairly water resistant. 

- There are actually a lot of pretty good options from Urban Outfitter if you’re looking for something cheaper.

The Ben Sherman Hooded Jacket

The GANT Rugger Downer Puffer Jacket

The CPO Cotton Slack Jacket

- You could also go with this Harrington Jacket from Polo Ralph Lauren at Mr. Porter. It’s kinda of a niched style, but I feel like you could cater it towards a lot of different looks.

Best of luck!

Even though anonymous questions/statements can go both ways, I love how some people really open up with honest kindness :) 

The most sincere of thanks, I’m so glad to have you as a friend too!

shocker. not gay. never gay. I would hope that was at least kind of obvious, practically every other thing I post is talking about how awesome I think girls are haha.

you.

haha it’s a very rare occurrence,  but I would love it if a girl asked me out for coffee, especially if we didn’t already know each other! As I’ve always said, I love when I girl is confident :)

It’s just the best thing ever! sucks. Always Never having to think about money is awesome shit.

If the benefits out way the consequences then yes absolutely yes. Every situation surrounding love or some form of love needs to be handled differently, but I think as long as confessing your feelings to someone doesn’t cause anyone to suffer, then you should never hesitate. If it does however, you need to make the hard choice of whether or not you’re crossing the line of morality, and your words are better left unsaid.

Sitting on the couch in my boxers, with an entire pizza on my lap, watching a batman marathon on TV. Yes I am that cool. haha :)

I would remove the word moist from existence.

I’d say there are a few different directions you could go, I’ve actually never been to a wedding, so I can’t give you an example of something I’ve worn, but I’m sure we can come up with some that will keep you looking steezy while still being formal enough to talk about cribbage with your grandparents. 

When I shop for a pair of shoes, given my college student “broke” status, I’m usually on a pretty strict budget. I research the style/material/color/ect. of shoe I’m looking for, and then hit countless thrift stores until I find my prize. So depending on your time limit you might want to give that a try. You’ll obviously want a black shoe, probably leather or suede, and if the brand is unrecognizable you’ll want to check for quality of the material and the stitching in sole. As the heel goes, a pretty good rule of thumb is, “a single piece rubber sole means, put the shoe down and walk away.” That certainly isn’t always true, but most often you’re looking for something with a layered wood/compressed rubber sole and heel.

When you’re not searching second hand, you have a little more freedom to move into canvas and other materials, not having to worry about the condition of them. In the realm of actually making an investment for some new shoes I would suggest these:

Under 20$: Some black espadrilles if your pants have a more fitted cut. ASOS makes a pretty rad pair that are like 8$ on sale right now.

Under 75$: Some all black TOMS again only if your pants have a more fitted cut, either the Burlap or Canvas, velvet only if your feeling crazy.

Some black canvas Cadwells from ZURIICK

Under 100$: There’s a pretty reasonable pair of Generic Surplus black canvas oxfords that are really nice.

Some black loafers from OAK are always cool, and they’re on sale. They have some other really nice pairs at a good price if you look around.

Under 250$: Always an excellent choice, especially to maintain a formal fashun is COLEHAAN. I would suggest either these, or these.

Under 500$: Mark McNairy obviously needs to be in this list, these dark grey bucks would be sweet.

Some wingtips by Paul & Co. at Brooks Brothers.

500$ and up: If your wallet reaches this end of the list my friend then the world is your oyster and I salute you.

Some lace-ups from YSL

  Some brushed leather oxfords by LANVIN.

Several choices by John Lobb, if I had to pick, maybe these or these.

Good luck.