Ask dapperQ: How to WOW in a Jeans & Blazer

A reader writes:

“I need help! I’m 18 years old and a butch lesbian. My girlfriend will soon be 19 and we are going out for her birthday however my dress sense is horrible and I want to impress her. Is there any chance you can help me because I feel like she doesn’t look at me because I don’t ‘WOW’ her. I like jeans and a blazer, however I can’t look decent in it. I need your help!” – Hayley

First of all Hayley, if your girlfriend doesn’t look at you, your biggest problem is your girlfriend, not your wardrobe. It seems to me that you are not with someone who appreciates you the way you deserve to be appreciated. If she is not wowed by you every single minute – the moment you wake up; on Saturday morning in sweatpants; in the worst possible outfit you have ever braved to wear in public – then she does not deserve the amazingness that is you.

Now, that said, perhaps you just wish that your “dress sense” be more reflective of the incredible person that you already are. That I can help you with. It sounds to me like you really connect with wearing jeans and a blazer. So let’s go with that. Here’s my advice for wowing up your jeans and blazer attire so that when a girl comes around who appreciates you for exactly who you are, you will feel confident enough to approach her.

1)     Fit: Let’s face it,  it can be hard to find affordable butch clothing fit for a female body. I am sure you have shopped in the boys/men’s department only to find that your blazer doesn’t quite fit right. Or, you’ve bought a women’s blazer only to be like, “WHAT is this fitted situation all about?” I recommend finding a tailor and investing in getting the jackets that you already own tailored to fit your body. My guess is that you like the jackets you have, so why not keep them as the center of your wardrobe? For the cost of what you might spend on new clothes, you can get the clothes you already own fit in way that rocks just a little more.

2)     Classic Dapper: There is something about the oh-so-presentable-you-could-meet-my-parents classic dapper look. There is nothing I love more than a little dapper flare to jazz up a jeans and blazer outfit. A simple pocket square or tie can add a whole new dimension to your wardrobe and give you more variety without purchasing a slew of new outfits.

Classic dapper

3)     Undress-me clothes: You are 18 now, so I will assume you are ready for this conversation. There is something special about the kind of butch clothing that makes my mind wander to how “I am going to take it off?” Button up shirts beg to be unbuttoned. Ties beg to be untied. A pullover shirt or sweatshirt just doesn’t have the same allure for me (as a butch loving Femme) as things that button and tie.

undress me

4)     Layers that breathe: Keeping #3 in mind, be careful with layering. I don’t want to imagine an hour’s worth of undressing you. If you wear a sweater, put a button up underneath. If you have a polo shirt, try to avoid a sweater over it and an undershirt underneath. I don’t want to be lifting a million different pieces of clothing over your head. (I don’t mean to imply that clothing will always come off; but, you know, we femmes have active imaginations). Keep it to one “over your head” item per outfit.


5)     Shoes: Never underestimate the power of good footwear. Don’t leave the shoes as a last thought. There are so many amazing things happening with footwear these days (and socks too!). Check out some great ideas below. I also recently discovered this gem of a company where you can design your own shoes. They are a little expensive, but that’s what birthdays are for right? Put these on your wish list!

*For more inspiration on how to create wow jeans/blazer combos, check out Ellen DeGeneres’ Pinterest page. She always has great casual cool style:

In this photo released by Warner Bros, talk show host Ellen DeGeneres addresses her recent visit by the paramedics during a taping of "The Ellen DeGeneres Show" on Monday, September 26th in Burbank, CA.This episode will air on Tuesday, September 27th.Photo Credit: Michael Rozman/Warner Bros,

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  • I only had to read the first paragraph to know that this whole advice column would be spot on. First and foremost, surround yourself with people who know you are awesome!
    I would add as an alternative-addition-to the part about layers – if you want to keep a layer of cloth on no matter how much clothing comes off, choose Items of Power to wear as a skin beneath date clothes. Fabric, fit, and color should all be such that you're ready to rock them from the deepest dark, to the light of morning, when you just may be called upon to find and learn how to operate the nearest coffee making device. 🙂

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