What A Woman Wants: Ashley Weston

What A Woman Wants: Ashley Weston

The celebrity menswear stylist on leading men and wardrobe must-haves
ashley weston, what a woman wants, mens style, men's stylist

By Megan Collins | Last Updated: Mar 18 2018 | 7 min read

Scroll through celebrity menswear stylist Ashley Weston‘s Instagram feed, and you’ll spot more than a few SG Men’s Style Madness contenders. The Southern California native has dressed some of Hollywood’s biggest names, including Jon Hamm, Harrison Ford, Rami Malek, and Rob Lowe. Not surprising, as Weston’s friendly and relatable approach to style would put even the most fashion-averse guy at ease. We got her to take a break from dressing spotlight-stealing stars to share her take on the best (and worst!) of current men’s trends with Style Girlfriend.

Read on as Ashley Weston tell us what a woman wants:

ashley weston, what a woman wants, mens style, men's stylist

{Weston with Mr. Robot’s Rami Malek, via NYT}

When did you decide to focus on exclusively working with male clients in your styling business?

I started out styling both men and women celebrities, but at one point I had a really bad experience with a female client that pushed me to work exclusively with men, which I always preferred anyways. She wanted me to style her for a premiere just as I was about to leave town for a big family reunion. Long story short, she demanded that I miss my reunion and I fired her over the phone while boarding my flight as she screamed about how I’m ruined in the business and she was the best thing to ever happen to me – I’ve never had another female client since.

You believe (like we do here at SG HQ!) that the way a man feels about the clothes he wears impacts every other area of his life, from dating and work to overall confidence. What’s an easy way for a guy to instantly level-up his wardrobe?

A well-fitting, crisp white dress shirt and a pair of dark wash jeans looks amazing on every guy, no matter his age or body type.

ashley weston, what a woman wants, mens style, men's stylist

{A few famous faces from Weston’s portfolio, l to r: Jon Hamm, Chris Pratt, Liev Schreiber}

Working with clients for entertainment industry events like the Golden Globes and Oscars involves a lot more than a quick trip to the fitting room. What’s one thing you wish people knew about your job?

There’s a huge misconception that men have it easy when it comes to clothes. People think that all they need to do is throw on a suit or tuxedo and get it tailored, right?


There’s so many tiny details that go into making a standout, sharp-as-hell outfit for my clients that it’s literally a full time job. Also, people think that I just shop for my clients and hang out with them – I WISH it was that easy.

Most guys don’t have designers lending them items straight from the runway for a big event. How can they look like a million bucks without spending a fortune?

Tailor, tailor, tailor!

Keep it simple and timeless with your clothes. And make sure if you’re wearing a suit, add a pocket square, tie a half-windsor knot (that knot better have a dimple in it,too!), and wear non-scuffed, clean dress shoes.

ashley weston, what a woman wants, mens style, men's stylistHave any red carpet etiquette “do’s and don’ts” you dole out to help clients put their best foot forward during these highly scrutinized events?

Yes! I always tell them, just before they step out onto the red carpet, to check to make sure their shirt and jacket sleeves are pulled down. Sometimes they ride up, so just give them a quick tug so they lay in their proper place.

I can go on and on, so I’ll leave with this last one that’s a big pet peeve of mine. One of my clients even mentioned me and my quirk on the Live! With Kelly and Michael show: Make sure shoelaces are tucked into the shoes. There’s nothing sloppier (and visually annoying) than seeing shoelace loops sticking out from underneath pants. I’m going to dedicate a whole series to shoelaces on my website, haha! (I wish I was joking)

How important is it to build a relationship with your client?

Extremely. I tell my clients to look at me like an extension of their brain that handles everything clothing-related so that they can focus on their craft. I style my clients in clothes that they’d wear themselves but I just sharpen them up a bit.

You were an inner-city school teacher before making a jump to the fashion industry. Does that training come in handy when you need to discipline your clients on detention-worthy missteps like keeping their bottom jacket button unbuttoned?

That made me laugh! I don’t beat myself up or get upset with my clients if they make mistakes. They’re human like everyone else. It’s very hard to remember what to check for and do with your clothes, especially when they have to worry about a million other things like they do. So I’m never hard on them or scold them if they forget something. I’d forget things way more often if I was in their shoes!

The best approach is to be consistent with my advice and tips until eventually it becomes second nature for them. It’s all about baby steps.

Who is easier to work with – a client who has no clue about his personal style, or one with lots of (strong!) opinions?

I don’t think one is easier than the other. Both have their challenges.

ashley weston, what a woman wants, mens style, men's stylistNot to make you pick your favorite child, but… what’s your favorite recent look that you’ve styled (and why)?

Oh man, that’s tough. They all looked amazing this award season, and GQ and Esquire gave me the ultimate compliment by putting them on their various best-dressed lists. But if I had to choose, I loved Finn Wittrock’s Prada navy tuxedo look (right) from this year’s Academy Awards. Everything just came together perfectly and he looked like an old Hollywood leading man.

How does it feel to see clients of yours on best-dressed lists? Who gets more excited – you or them?

I definitely get way more excited – It’s the best feeling in the world because it’s the ultimate validation that I did a great job. I literally jump up and down with excitement and text them immediately. I love when my clients get recognized for our work together.

You and I caught up during the (jam packed) men’s fashion week here in NYC, what are a few of the favorite trends that you noticed?

I love seeing a lot of designers starting to incorporate high performance fabrics into their clothing. Men move around in their clothes and need to wear items that looks sharp but also stay comfortable throughout the day. I’m curious how it’ll develop over the next few years.

What about the trends that you’d just as soon leave on the runway?

I’m sick of joggers/sweat pants. Athleisure needs to stop. Gym clothes belong in the gym and only in the gym.

Give us a list – any guy who wants to look as good as one of your star clients should have X, Y, and Z in their closet:

Every guy should have a pair of nice fitting, dark wash jeans, and navy sport coat and a pair of black Oxford dress shoes in his closet. Throw on a white collared shirt underneath the jacket and you’ll look sharp and put together.

ashley weston, what a woman wants, mens style, men's stylist, wardrobe essentials

Jeans: AG, $140 | Sport Coat: AMI, $199 | Shirt: J.Crew, $70 | Shoes: Johnston & Murphy, $155

What’s your personal definition of great style?

Classic, timeless, sharp yet understated clothing epitomized so well by Paul Newman and Marlon Brando.

Favorite city (or cities!) for men’s style?

Paris, London, and Italy! Men take a special pride in the way they dress that I find extremely sexy.

ashley weston, what a woman wants, mens style, men's stylistQuick Hits

Favorite grooming item you’ve stolen from a guy

Kiehl’s Facial Fuel face lotion – It says it’s made for men’s skin, but I’m addicted!

Grooming item you’ve had a guy steal from you

My La Prairie eye cream which is super expensive, so I wish they would stop!

Top song played on Spotify

I still haven’t gotten sick of playing Adele’s “Hello.”

Peacocking: yes or no

Hell NO.

Athleisure: yes or no

Double no.

First celebrity crush

Leonardo DiCaprio circa Romeo & Juliet and Titanic era.


LA!!! I’m biased since I’m a native Angeleno, but it really is a wonderful city.

Coffee or tea


Chinos or jeans


After parties or premieres

After parties! Premieres are really boring, actually.

Tell me:

How do you define great style?

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I started Style Girlfriend to help guys look, feel, and act their best.